Dating is a ruthless game that can either result in new beginnings or broken hearts. Unfortunately, the following stories demonstrate the latter outcome—these bad dates are so unbearable, it makes you wonder how anybody can manage to get into a healthy and stable relationship nowadays. Read on for some blood-boiling tales:
1. Coming On Strong
He told me to meet him at a bar, which turned out to be a hole-in-in-the-wall in a strip mall, literally just a bar, no food, just booze. We were supposed to be having dinner. I had put in some effort with a cute outfit, nice makeup, etc. When he showed up, my stomach dropped. He had ratty old jeans and a paint-splattered hoodie. That was the moment that made me think "ohhhh this is gonna be bad."
Still, he'd already caught me, so we sat down and the bartender immediately put a pint-glass of tonic in front of him before even asking what I wanted. Clearly he was a regular. We tried to make small talk but he was just so weird. He was cutting me off mid-sentence with random nonsense, buddy-punching me on the arm, and kept hurrying me to finish my drink so I could keep up with him.
I finished my one light drink, paid for it (which offended him deeply), and got up to leave. Then it took another turn. He chugged his last drink, threw a $100 bill on the bar, and followed me into the parking lot. I tried to get away politely and he interrupted with "Come back to my place, I go like a freight train." I stumbled over my "Ah, no thank you" and before I'd finished the sentence he got into his car, started the engine, and screeched out of the parking lot, almost getting it onto two wheels on the turn.
There were some interesting characters back in the early days of online dating. 2004 was like the wild west.
2. Change Of Plans
I went on a date after talking with someone for a couple of weeks. The conversation online was pleasant and involved the usual small talk about hobbies, interests, etc., There were no red flags, or so I thought...We arranged to meet in the city for a coffee. When I arrived and she was already there...and she looked nothing like her pictures.
I thought to myself, "Oh, well most people tend to embellish their photos. Let's see what she's like in person." That's when I messed up BIG time. We got to talking and at one point, she asked me what I'd be doing the following weekend. I love camping and exploring, so I just told her I had a camping trip with my mates.
She asked me if she could come along and I replied, "Um, no...We only just met." She then proceeded to lose her cool, throwing a tantrum as if we'd.been dating for years. "How dare you not take me along," she snapped at me. Yet, even after she caused a scene, my idiot self decided to see the date through to the end. She continued to ask me more questions about the trip, asking which campsite I'd be going to.
I gave her a rough estimate of the location and she replied, "Oh, that's nice. I'll see you there..." I thought that was a weird response and reiterated that I was not comfortable with that. She replied, "No. I'm going there no matter what you say. You won't see me coming." She then let out a maniacal laugh. That was the last straw for me. I stood up, placed my money on the table to pay for my coffee, and walked away.
3. Too Close For Comfort
I dated this girl who was a friend of a friend. She used to come into the pub I worked at for $10 steak night with her mom and a guy who we weren't sure was her boyfriend or brother...turned out it was her brother, but they were weirdly close. Anyway, we went on a date, and she seemed quite uncomfortable the whole time. Didn't make much conversation, just obviously wasn't into it.
So I dropped her home, and she asked me if I wanted to come in. Against my better judgement I did. They had two couches in the living room. I sat on one awkwardly while she laid on the other couch and spooned with her brother. At this point I realized I should not have shown up...Every time she left the pub from then on, her and her brother left holding hands.
4. Three’s Company
I met a girl on Craigslist. After a few messages, we set up a date at a bar downtown. I showed up and there was an unexpected surprise waiting for me at our table—she was already there with a guy friend. No biggie; I just assumed she was playing it safe. They were at a two-person table and the place was packed. They already had drinks, so I grabbed one for myself and put it on my tab.
My date and her friend proceeded to ignore me. I tried to join in on their conversation a few times but neither of them acknowledged me. Even when I directly spoke to them to get their attention, I got one-word answers with attitude. So, I finished my drink, paid my bill, and left without saying a word. Later, I get a barrage of messages from her calling me mean and awful for sticking them with their own tab.
5. Doing An Ex A Solid
I matched with a girl on Plenty of Fish. We were talking for a while and she worked out she knew someone I had worked with in the past. I asked the previous co-worker what she was like and he said she's ok and not “mental or anything.” Little did I now, this was an evil plan. He actually really didn't like me because I was better at the job than he was and he was straight up lying his butt off.
So I arrange a coffee date between our houses. She only lived like 5-10 minutes away and the nearest shopping centre cafe was 10 minutes away. I arrive and wait a few minutes and in walks this girl 20-30 lbs heavier than her display picture with a baby in a pram. She recognized me and sat down like this was normal. Now see, she'd told me she had a daughter who was two.
I told her I had a two-year-old son as well. Turns out, her daughter was two months not two years and she never corrected the fact. Also this is the first time we had met and she asked me five minutes into the date if I could buy her baby formula. One look at her and I could tell she actually needed the formula and was in a desperate situation, so I bought it for her because I'm a sucker and didn't want her baby to starve.
I then politely told her it was never going to work because she straight-up lied. She said yeah fair enough and left. But that wasn’t the end. About two months later, I was talking to another girl on Plenty of Fish who happened to be friends with her. She seemed normal and not like the complete psychopath I'm sure she was. The crazy one from the first part of the story rang me (she stalked me through my friends) and told me how the second one was mental.
I said I didn't believe her and she hung up on me. Ten minutes later my messenger starts going off, it's girl #1 sending film clips and news articles of girl #2 having a complete psychotic break and torching her ex boyfriends car...on camera in a shopping centre. So it all worked out well and I dodged the bigger bullet because girl #1 thought I was too nice a guy to deserve girl #2.
6. Small Town Woes
I was on a dating app in a smallish town and I had already gone on a few boring dates. But eventually, I matched with this one girl who agreed to meet with me. I was thrilled, but there was something very odd about her and the conversation we had. She was eager to meet; almost too eager. I got to the Starbucks and waited inside for about twenty minutes past our agreed meet time.
The girl texted me to tell me she was running late, and she asked me to stand outside so she could see me as she drove by. I looked over and there ws another dude standing on the sidewalk with his phone in his hand. I recognized him from the gym, so I asked him if he was also meeting a girl. It turned out the girl was pulling a fast one on us both as revenge for her girlfriend who we both apparently dated.
7. A Blank Slate
When I went on this date with this dude, and he had 0 interests. When I tell you 0, I mean it. He didn’t watch movies, series, did not listen to music, did not watch TV, didn’t have any hobbies, did not have any siblings, any friends, any work, just university studies. He didn’t like to cook or clean or even go on walks. It was the most awkward date I have ever been on with someone.
He was studying Economics, he lived alone, and was an unemployed student. We met on Tinder, and both his pictures and our conversation there seemed normal. I thought he was just shy. But no, he was the most boring person I have ever met in my life.
8. The Sound Of Silence
On our date, we went to Dave and Buster's. I could tell she was uncomfortable. I tried to bring up topics for us to talk about, but I was only getting one-word answers or literally, “I don’t know,” even when I asked her questions about herself. We sat in silence for about five minutes before she finally showed signs of life.
She got up to go to the bathroom and when she came back, I just straight up said to her, “Hey, if you’re not having a good time, you’re more than welcome to leave. It’s perfectly fine.” That's when things went completely south. She got insulted by what I said and picked up her purse to leave. I repeated myself and said, “If you’re having fun, I’m more than happy to stay, but like, we’re not even talking right now.”
So she got up and left and I ordered another drink, waited a bit to watch the rest of the game on TV, then left. I got a text from her saying how insulted she was that I would ask her if she wanted to leave, etc. I just said, “I tried talking to you for 15 minutes and got no responses.” She then explained that sometimes she just doesn’t feel like talking and I was cruel for not being okay with that.
9. You Again
I went on a date a few months after my college girlfriend and I had broken up. I had matched with this girl off of Tinder and we messaged a bit. But there was one really weird red flag. She was relentless about wanting to know more about my ex and how I felt after the break up. I looked past this and met her for dinner a couple nights later. This was an enormous mistake.
I walked in the restaurant and my ex is sitting at the table under that girl’s name. I turned around to walk out and got a Tinder notification from the girl I had agreed to meet saying, “You’ll never be able to get away from me.” Should have stayed home that night, and steer clear of blind dates.
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10. A Quick End
I sat down and he immediately said, "Oh yes, you are hotter than your pictures and you're my girlfriend now." Cleary, he came on real strong. I chalked it up to keenness at first or maybe a weird sense of humor. I figured I'd at least stick around for a drink or two, just to feel it out. I even offered to buy the first round, partly as an excuse to get away from the table for a second.
I made some unrelated comment to the bartender that made him laugh, and when I got back to the table, my date caught me completely off guard. He started yelling and slamming his fists on the table, demanding that I tell him what I said to the bartender and whether I thought he was good-looking or not. He had somehow gotten jealous of this bartender five minutes after meeting me.
11. Seeing The Light
I went on a date with a guy on Tinder. He was a co-worker of one of my friends, so I figured he'd be alright. First date was decent enough so we went on a second. This date was also going well until I mentioned his pentagram necklace, asking if he just liked the design or if he was Pagan. He either did not wear this necklace to the first date or it had been under his shirt.
He replied Pagan, and I said how I found the Pagan religion to be very interesting and was hoping to hear more about it. Oh boy, I wish I didn't. He had been fairly shy up until that point. He did a complete 180 and started going on, very loudly in this fairly nice restaurant, about how his mother could physically heal people just with touch and about how his friend was in the army and got shot in the leg but didn't feel any pain from it because my date had linked minds with him from across the world and took all the pain for him instead.
I managed to get through the date and when I got home, I messaged to say it wasn't working out, that I didn't feel any spark after two dates, and wished him well. He immediately blocked me. I then messaged my friend, who was his co-worker, asking if the Pagan talk was normal for him. Friend calls me to cry from laughter over the phone about how he and all the other co-workers knew he was crazy but also knew he was harmless so wanted to see how I'd react to him.
Bit cruel on my friend's part to not warn me, especially since he knew I was going on these dates, but I definitely wasn't going on a third regardless.
12. Miscommunication?
I had a crush on this guy in high school and my friend kept urging me to talk to him. I finally got the nerve to ask him out and apparently, he liked me too, or so I thought. We talked often and exchanged notes in the hallway. He even asked me to homecoming and I said yes. I was so excited; I bought a new dress and everything!
But when I got to the football game, everything changed for the worst. I saw my crush in the stands and I told him I was going to go sit with him for the game. He told me I couldn’t do that. I asked him why and he said it was because he was with—get this—his girlfriend. I was devastated and embarrassed, to say the least.
13. Three’s A Crowd
I met a girl at a bar and things clicked well. Went on a date a few nights later and she shows up with her “sister.” I didn’t think anything of it at the time. Figured she was being safe possibly since we just met. But this happened two more times. I finally said can we go out without your sister and she seemed insulted at the idea. I found out months later she had no sister, it was just her friend and they did everything together. It was truly strange.
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14. Why Did He Even Come Over?
I invited this guy from Tinder over to my place because he seemed pretty nice and we had a lot in common. He was decent looking on his profile, so I thought, why not? For context, I had just moved into my apartment and I didn't have a nice setup yet besides a table and a few chairs. The second he walked in, he waved the first red flag—he asked me why I didn't have any slippers for guests.
I was a bit confused but figured maybe he just lived in a fancier household than me (and yes, he made it clear he did). I said I didn't have any slippers, and he just shrugged it off. We then went to my balcony to hang out and he spent twenty minutes crying about how much he still loved and missed his ex-girlfriend. I just nodded along to be nice, but it was strange.
We eventually went back inside and he immediately started grilling me about my lack of furniture. "Where’s your TV? Couch?" When I explained that I didn't have the money at the moment to buy nice furniture, he scoffed and just kept nitpicking.
15. The Only Living Girl In San Francisco
We had gone to the Burning Man holiday party. I'm a volunteer so I get an invite and two drink tickets, but she hated it and made me take her to a nice restaurant around the corner. It was a nice place in the Dogpatch neighborhood. And I guess the whole time the staff slowly came to hate her and worry about me. She didn't like anything and didn't look at the staff much.
When I drove her home, she accused me of being a recruiter for a cult. I still asked her out again, though, God knows why. I showed up and she had forgotten so we went to a deli next door where she got in an argument with some street guy she seemed to really vibe with. I finally lost interest when we were walking very fast in a random direction and she went on about how she was the only person in San Francisco opposed to assault.
I gently disagreed so she turned and walked away. Should I call her?
16. Maybe She’s A Werewolf
I went on a date with a girl in college, a cutie from my class who I had been trying to get a date with for a while. I picked her up to drive to dinner, and it’s worth mentioning I live in Wisconsin and it was January, so it was pretty cold outside. While I was driving, she startled me with her next move—she proceeded to undo her belt, open the door, leap out of the car into a snowbank, and run into the woods.
I had to chase her down and convince her to get back in the car with me before she lost her feet to frostbite. We didn't date anymore, but I did check in on her every once in a while.
17. Secret Messages
She texted me an apology for the date while we were still on the date. Long story short: she arrived late, then friends of hers "just happened to be walking by" and they joined us. Clearly, their intention was to use me for free drinks, which they immediately began guzzling down as quickly as the server could bring them. I realized what they were doing, so I made sure to pay for my drinks in cash, which meant I didn't have a tab going.
I tried to give my date the benefit of the doubt in hopes that her friends would leave and we'd actually have a date, but she seemed more interested in getting their approval. At one point, she was staring down at her phone, and then mine started vibrating. Normally, I'd never check my phone while on a date, but this date was a disaster, and she was obviously staring at her phone, so...what the heck.
I looked down at my phone and saw a one-word text…from her. It just said “Sorry.” I looked at her, then I looked at my phone again, and I just shrugged. Whatever. There was a gasp when I got up to leave. One of her friends protested because I didn't pick up the bill for the whole table. I said, "I already paid for mine." Then I walked right out of the door.
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18. #BadDate
My date got mad at me for wanting to leave when all she did the entire time was mess around on her phone and post selfies of her and the coffee I bought her. I checked her Instagram profile later on (she wanted me to follow and like her photos) and the caption was disturbing. It was something like, "Treated myself #blessed #sogood #coffee.” And yet, she couldn't hold a conversation at all.
19. He Almost Fooled Her
I went on a couple of dates with a guy who genuinely seemed really nice. For our third or fourth date, he invited me to go tailgating with his family, who I clearly didn’t even know. I said yes because I’ve never been tailgating before. He quickly made me regret saying yes. I went over to his place and was invited into his room. There was no bed frame, no sheets, crumbs from food everywhere, clothes were partly folded on the floor, it was dimly lit, and the carpet was crusty enough that it had gotten stiff/hard.
Absolutely disgusting. His family ended up being friendly, but when it was time for me to go that night, he quite literally pouted like a child and initially refused to take me home. I should’ve drove myself, but didn’t. Hindsight is 20/20. On our way back to my house, he started talking about how he was going to spend $10k on an engagement ring for me and how he wanted to marry me “so badly.”
He also brought up that his last “girlfriend’s” father threatened to call the authorities on him if he didn’t leave her alone. The following day, I texted him and said that things weren’t going to work out. I blocked him after he messaged me really weird things and said he “just wanted to get a reaction out of [me].” I just hate how the red flags didn’t pop up on the first couple dates.
20. A Whole Mess
When we went back to my house after a bike trip, she fell and broke her cervical spine. I had to take her to the ER I work at—she got admitted and put into a halo in the ICU. I met her family there. We dated for something like nine months after that, but then she totally ghosted me. Months later, out of the blue, I got served by a sheriff—she was suing me for a million dollars over her injury.
It went on and on and even to trial. It came out she had lied to me and was still married when she went on date with me. Worse yet, she ghosted me because she was also cheating on me with another guy and she was pregnant with him at the time. He even testified about her disability at the trial.
21. Dr. Jekyll And Mr. Hyde
I met this guy on Tinder. He seemed really cool. We started texting for a month or so and later planned to meet at this tavern. It was hard trying to find him because the place was packed. When I do see him, I guess he’s tipsy. But he didn’t seem like completely out of it, he was functional. I tried to ask him questions and get to know him in this sort of loud and busy space.
The whole time, even though he’s inches away from my face, he can’t hear what I’m asking or saying. Mind you, he invited me to this place, I’d never gone here before. This was supposed to be our first date. He proceeds to buy me a pint and kept slapping me on my backside, quite forcefully to be honest. This is my first time meeting him. We get the drink and he asks me “Do you want a drink?” Alarm bells start going off.
I tell him he just bought me one. He asks this question annoyingly over and over again as if he forgot he asked already. This goes on for at least an hour…All the while I’m trying to kick it with him. Play some outdoor bar games and such. And he’s asking, “What are you doing here?” And I’m like “I’m on a date with you?” He asks me this question over an over as well…
I don’t get how anyone is that incoherent. He wasn’t that far gone, he couldn’t have been. Even if he was, when we texted he seemed fairly intelligible and kind. But the whole night he probably only asked me two or three questions, the same ones, over and over, and kept slapping me on my backside. There was a point we were going to congregate with his friends and I sort of lost him in the crowd and LEFT. Very rude and weird.
He had the nerve to call me and asked where I went. I told him I went home. He said he wanted to get to know me, and I was like yeah, maybe another time. Like dude you had the whole night to try. He had no intent to make a real effort. I blocked the heck out of him.
22. At Least She Didn’t Feel Awkward
When I was in high school, I went on a date with a friend of a friend. We went and saw a movie, then went out for dinner. I was nervous and awkward, and it ended without much fanfare. The date went OK, and there wasn't a second one, but that's not the bad part. About a month later, I went to a party at our mutual friend's house.
I saw her there and was afraid it might be a little awkward. I had no idea she was invited. About an hour into the party, she came up and started talking to the mutual friend, while I was standing nearby. After a few minutes of talking, the girl I had gone on a less-than-awesome date with came up and introduced herself to me.
23. Honesty Isn’t Always The Best Policy
We had a great time at dinner, and went for a walk through a park afterwards. We're walking along and talking. Then she makes a shocking confession. She mentions to me that she is still "technically" engaged to a guy, but she was only marrying him because he had gotten her pregnant. But she had had a miscarriage a few days ago (had not told him yet), and now that there was no baby and she had met me she was going to tell him and break up with him.
There was no second date.
24. Truth Is Subjective
I invited a girl from Tinder over to my house after a very steamy conversation (led by her). After bringing her to my place, she proceeded to absolutely ignore me and at best give me one-word answers to every line of the get-to-know-you conversation, acting like I was inconveniencing her by taking her attention away from her phone.
Any time I tried to make a move, I got shot down instantly. This went on for a few hours, so I put Netflix on. Big mistake on my part, apparently. Just as I was about to say it was time to leave, with no warning whatsoever, she straddled me and started aggressively making out with me. It was disgusting—a bunch of food residue from her mouth got into mine. She hadn’t brushed her teeth.
I noped out of that and we had a very quiet drive back to her house. Before I even left her driveway, she was texting me saying how great it went and that she wanted to see me again soon. Needless to say, that did not happen!
25. Don’t Follow Your Dreams
When he went on a long and obnoxious rant about how my job at the time (assistant welder) was "stupid and a waste of time" and that I should become a dental hygienist, a job I have no interest in, because "at least it has a future." The whole date itself was AWFUL. But it was at that point I realized, we were not a "match," to say the least.
26. You’re As Old As You Feel
I went on a date with a guy on Bumble. We made plans for him to pick me up and go to a local restaurant for dinner. It ended up snowing the night before and the road had developed a layer of ice on top. I suggested rescheduling, but he insisted. He picked me up, and when leaving my neighborhood, he started to slide on the ice. My life flashed before my eyes and we ended up rear-ending the car at the end of my road.
Thankfully, everyone was okay. I was pretty shaken up, but we continued on with dinner and the rest of the night was pretty mild. The following Monday, his insurance ended up calling me, asking what happened. I called him to say I didn’t want to get any further involved after having spent forever on the phone with the adjustor and he responded by asking me out.
Not only that, but he ended up standing me up anyway. He claimed, “in his older age” he tends to be more forgetful…He was 27.
27. Never Gonna Get This
I didn't show up for this date, and I was always super proud that I trusted my intuition. I had a date scheduled with a guy at a nice place downtown that I had agreed to. Right before the date he leaves me a message that we're going to a different place. I look it up, and it's a dive bar out in the middle of nowhere. Like in a field. Alarm bells started going off.
I actually really liked the guy and went back and forth with myself before I call the guy back and get his voicemail. So I leave a message apologizing profusely, but I need to reschedule the date. I also add that I'd like to pick the place this time. Alarm bells are still going off and I end up letting his return call go to voicemail. I'm glad didn’t pick up. His message sent chills down my spine.
I had to listen to it twice to believe it. This grown man proceeds to scream at me, calling me every name in the book. Calling me a witch, etc. Telling me how I missed out on the best date with best guy of my life. That was the most happy I'd been I went with my gut and skipped out on a first date.
28. You’re Focused On The Wrong Thing
My date phoned me the morning before our date at 2 am to say she was so excited about our date. Then, mid-conversation, she crashed her car. After that, I didn’t hear from her until the date—I had to pick her up at that point because totaled her car. The date started well and I took her to a fancy sushi place, but she did not eat one piece as she was talking the entire time.
I slowly established that she had not slept for a few days and her eyes were rolling. I settled the bill and took her home to a very judgmental roommate. As I was walking back to my car, I heard a bloodcurdling shriek..."Where is my goodnight kiss?!" My anxiety kicked in and I started running to my car. I looked back and she was chasing me, still screaming.
Neighbors from all over her complex started watching from their homes but I somehow managed to escape. Months later, I ran into her roommate out on the town and she said, "Oh yes, you were the one who ate all the sushi."
29. A Lie Of Omission
Weirdest date I ever had? Probably the time she was hiding the fact she had a baby. She didn’t say anything about that when we were texting each other days prior. But that wasn’t the deal breaker. The deal breaker was the fact she had a baby and was alcoholic that couldn’t keep herself under control and also mentioned that her ex (currently behind bars at the time) didn’t really “break up” so I figured she was trying to keep me as around as a rebound.
30. It’s Too Much
I met this guy Ron on OkCupid. He seemed nice enough, even though he was older than his profile said. We chatted over the phone a few times and he came across okay enough to meet. So, we did. I went to his house for the first meeting because I was honest in telling him what wouldn't be happening. I figured he was gentleman enough to respect my wishes.
We chatted for a while on his back porch and watched a movie in his living room. But then he started to act weird around me—he would grope me and I reminded him that wasn't happening and to please stop. "You're just so beautiful, I can't help myself." He could help himself. I was suddenly "very tired" and wanted to head home. He started texting me, just constantly bombarding me with compliments and it was smothering.
I talked about boundaries with him, but he just ignored me. He even offered me a key to his house. so I could pop over anytime. He wanted to get a dog so I could come over and walk it while he was at work. He also mentioned a work trip to Hawaii several months in advance and told me he wanted to take me. I started to pull away from him a little and explained that he was being too much too fast.
After a long break, we decided to meet up again because I make bad choices sometimes, admittedly. Things just got worse from that point on. He started groping me again, smothering me. He legitimately would not leave his hands to himself, so I leaned forward on my knees so he couldn't touch me. I told him I was leaving and he walked me back to my truck because it was late and dark.
He hugged me and wouldn't let go. I tried pulling back and telling him to let go, panicking, but he wouldn't. I started to nervously laugh because I was in full panic mode. I opened my door and he stood beside it, not letting me close it. I couldn't drive my car forward because I was in a parking garage and there was a car in front of me. If I go reversed, my door would have probably gotten torn off.
When I went ballistic and screamed at him to move, he backed up, made a snarky remark, and I finally went home. He started texting me again—long, long paragraphs about how when I "hugged him" he felt sparks he'd never felt before, how I mean so much to him, and how he's never felt this connected. I just stopped responding.
He started texting me more, I don't answer. Then he got mean, but I still didn't answer. I headed to work the next Monday and showed the text messages and his face to security and told them to not let him on campus. Security couldn't believe the text messages. I learned my lesson BIG TIME with him.
31. Now Let’s Talk About Me
I’m not sure what was the exact moment I realized I shouldn’t have showed up to this date, but I think it was at some point during the first 10 minutes. She showed up 30 minutes late and her “apology” was “Sorry I’m late but I’m always late.” Then she spent the first 15 minutes talking about her ex who she just broke up with a mere three days ago. And it STILL got worse.
During the entire date, she asked zero questions about me and only talked about herself and her problems. Gossiped about her friends (who I didn’t even know at all). Spent 20 minutes showing me photos and videos of her cat. I usually like cats but I was really annoyed at that point. Complained about the ice in her soda. And spent the last 10 minutes of the date talking about how much she needs to pee but refused to use the public restroom.
I was so glad when that date was over.
32. What Did I Say?
I met a girl through a friend at a party and we went on a few dates. On one of them, we ended up at a hotel and decided to stay the whole weekend. The last night, after a few drinks, we were chatting under the sheets. Drinks, snacks, good times. Suddenly, she switched to a whole other conversation. Not a simple switching of subjects, either.
This was a quick and smooth transition from a real conversation to one that was between her and…someone else. I was confused, but I brushed it off. This happened a couple of times. The third time though, I had to say something; I couldn’t just let it go. It was horrifying—she was weirded out and was just as confused as I was when I listened to the things she said.
I told her it was like she had parallel conversations going on in her head. She became visibly frightened by herself and nervously panicked, ultimately breaking down and thinking she was crazy. I tried to comfort her until we fell asleep. I found out later she was diagnosed bipolar, but never really heard from her after that night.
33. Am I Bothering You?
I went to a movie with my date, and everything seemed okay. We decided to grab dinner after the movie, and she just straight got sucked into her phone. Like, more than anyone I've ever seen. After more than a couple minutes of just sitting awkwardly and dumb small talk, I asked her if she had something going on or if she needed to go. "No I'm fine, just checking all my socials and keeping up with a few convos. You know how it is."
No, I don't. We had already ordered, so I just sat there quietly for the next 20 minutes until I got fed up with it. I said "excuse me for a moment," got up and told our waiter to put mine in a to-go box, and sat in the waiting room. She never looked up the entire time. Paid the waiter for my meal, and left.
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34. Strongly Opinionated
I went on a date with a girl who suggested a restaurant but it was closed when we got there. She told me it was where she'd had her wedding reception after marrying her much older husband. Then, at the next restaurant, she revealed her true colors—immediately asked me how I felt about Trump while telling me how great she thought he was before I answered.,
Then she drank most of the bottle of vino we ordered, made rude comments in the restaurant out loud, and told me constantly that she made more than I did (I'm not sure if she was right, but it was a weird thing to care about regardless). She told me she forgot my name twice and spent the entire car ride back to her place trying to convince me Obama's birth certificate was a forgery.
35. The Wrong Kind Of Double Date
It was midway through the movie and she said she had to go to the bathroom. She then came back with her boyfriend, who I wasn’t aware existed. So he sat in between us and swapped spit with her while I sat. I just walked out and went home afterward. Didn’t say goodbye or anything.
36. Older, Not Wiser
I was 18 with a Plenty of Fish profile and I got catfished by this dude who was about 20 years older than me. We met at Starbucks and upon seeing him, I knew I was out of my depth, but I didn't know what to do so I went along with the date. Worst decision ever. He would ask me my interests and then shoot them down. For example, he'd be like: “You're into Harry Potter? I think that is so childish!”
I knew I needed to nope out of there, but he kept insisting I come over to his place. He used the fact he bought me a coffee to make me feel guilty. I agreed to go to a park but that was the most he was going to get. I said I had to drive separately as I had to go somewhere later and during the drive, I called a friend and asked her to call me in fifteen minutes to give me an excuse to bail.
At the park, he mentioned that he knew he was older and attributed that to my "strange" behavior. He found it so odd that I did not want to see his house—he explained that he only invited me because he felt a connection and knew I wouldn't want to meet him if I knew he wasn't like his picture anymore. Not long after my bailout call came, he became so cold and it was scary.
Thankfully, I slipped off after a very awkward hug.
37. A Mountain Of Lies
I met a woman and she went on a diatribe about how into mountain biking she was. I asked her if she'd like to go mountain biking for a date and several days later we went. I picked her up and her roommate gave me "that look," like "good luck." There were a lot of verbal (sassy/complaining) and facial clues that said "this is not the date you're looking for."
We got on the trail and within about five minutes I realized she was not in fact "into" mountain biking. She pouted the entire time. Afterward I dropped her off, and she said something like "I had a nice time" and all I could do was think "are you kidding me?" There was no second date.
38. The Divine Plan
I went on a first date with a guy after meeting him on a dating site. The phone calls went well so I thought, why not. We met at the mall. Right off the bat, I got a weird vibe. He proceeded to tell me how many kids we would have, and how he would spank them whenever they were disobedient. The guy was fully serious, too—he said we had to do it because "it’s what God wants."
He ended up following me to my car and I was thankful it was daytime in a busy mall with a security guard watching. He then tried to make out me, but I slapped him and drove away.
39. Child’s Play
He took a weird interest in me working in childcare. Kept bringing up kids and toddlers. Eventually he made it clear he wanted a lot of kids and wanted me at home taking care of them. Which…whatever, I like the idea of being a housewife. Just the way he came across was bad and misogynistic. He told me at one point he’s not touching the kids till they’re out of diapers. That’s my job.
At that point, I knew I had made a mistake. Problem was, he was also my ride since a friend dropped me off. Had to go home with him.
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40. The Wrong Film
The guy was hot and interesting, so I invited him over thinking we’d have some casual fun. He arrived and it was going fine—we had loads in common including film taste. We decided to watch a movie and settled on Nymphomaniac, which neither of us had seen or known much about. Little did we know what we were getting ourselves into.
It was a very disturbing film for various reasons, awkward and painful viewing. It totally ruined the mood. We finished the movie and mutually decided to end the date. I didn’t bother to arrange another date.
41. Getaway Car
When she asked if we could stop at her mom's house first so she could "grab something," then after 10 minutes of waiting in the car she came running out of the door carrying a baby and a woman was chasing her, screaming. She jumped in the car and started yelling "drive drive drive!" I knew exactly what I had to do. I turned the car off and got out.
It was her kid, but she had lost custody to her mother because of addiction issues. We had met on a dating site and she thought I would go along with her plan to take her child back. She spent that night in a cell.
42. Oldest Trick In The Book
I got to the restaurant first and waited outside. When he arrived, he was extremely energetic past the point of being normal. When we sat down, I could see his eyes were dilated and unblinking. I assumed by that point he had done some sort of substance before the date. We agreed to have one drink at the restaurant, then go somewhere else for food.
During the drink portion of the date, he told me he could get me a good job selling cars at his business and then asked me to move in with him to annoy his ex-wife. I just chuckled and brushed it off. I told him I'd meet him at the restaurant and he shocked me with his next move—he followed me to my car, got in on the passenger side, and wanted me to drive him there.
I was a little freaked out but I tried to roll with it. We got to the restaurant and the vibes were all off at that point. I was significantly freaked out, so I used the bathroom excuse to ditch him and leave. I got to the front and realized I left my purse behind, so I asked the hostess for help. I told her to please find a way to get me out of the date. Fast forward about ten minutes and a glass of pinot later.
The manager came in making his rounds to the tables, stopped at ours, and asked for my name. He said I had a phone call up at the front. Not the smoothest line, but I went with it. I told my date I'd be right back, then grabbed my purse and hightailed it out of there.
43. He Should Have Watered Himself Down
When he walked into the café we were meeting at with a 4L jug of water, plopped it on the counter, and told the barista to use his special filtered water for the tea he was ordering. Turned out he sells these water purification machines that optimize the PH...which he insisted was not a pyramid scheme (it definitely was). After enduring his awful sales pitch, he also told me he used to be a drug dealer and that he turned to selling water because "he's addicted to selling." But that wasn’t the worst part.
He also told me how he had “extremely old fashioned values” (his words) and that he is a very controlling person and can't help it. He said he hates when people waste his time and is looking for a wife. Every time I tried talking about anything, he would cut me off and start talking about himself. He offered me a ride home at the end. I politely declined and ran the second I was no longer in line of sight.
44. It’s Shark Week Every Week
She had a weird obsession with sharks. She had shark decals on her car, shark tattoos, and wouldn't talk about anything but sharks. After lunch, she revealed she had no money, so I had to pay. I was going to anyway, but for her to bring no money on a date and just presume I would pay was pretty insulting.
45. Dads Always Know Best
He got into a political rant about 15 minutes into sitting down at dinner. And then opened his mouth and goes “Minorities wouldn’t have it so bad if they just worked harder. Opportunities don’t just fall into white people’s laps.” I excused myself to the bathroom, went to the hostess, paid my half of the meal that I didn’t even get to eat, and walked out.
I then went home and told my dad, who then made me an awesome grilled cheese and a hug. He also said I should have just left him with the bill and I have to agree but I just felt too nice to do that.
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46. Multi-Level Madness
We met up at a café. Within the first minute, he pulled out a bunch of brochures and started telling me how amazing Amway and its products are. He told me all about how you could gain access to all kinds of cool events and stuff by becoming a sales rep, etc. I was pretty annoyed that I was scammed into an MLM pitch meeting and I told him so.
After I said that, he completely lost it. He got extremely angry and defensive. He said: "I'm not trying to recruit you! I knew you were from Michigan and Amway was founded there, so I thought it'd be a good topic!" Right. I told him I was leaving and asked the waiter for the check. The dude literally then screamed: "SEPARATE CHECKS!" at the waiter, drawing the attention of everyone in the cafe.
I started getting a bit freaked out and was scared to walk to my car because the dude was literally shaking with rage. I was terrified he'd try to follow me, so when we went outside, I remained standing by the café door thinking he would walk ahead to his car first. Nope. Instead, he took it as an opportunity to stand there and scream at me in the parking lot.
H was still insisting he wasn't trying to recruit me and said I ruined the date by accusing him. As if somehow him yelling at me in a parking lot is going to change my mind. Finally, I couldn't take anymore—I just went to my car, locked the doors quickly, and drove multiple circles before going home.
47. Don’t Just Be You
One of my first attempts at online dating many years ago was a total disaster. The girl wasn’t very bright, but she was really nice and absolutely beautiful judging by the pictures she’d sent me. As a little background, she told me she was 5’2 and worked out, and had an average to slim body. I didn’t think anything of her telling me her height because she asked me mine, and that’s not always easily deduced from photos.
But her telling me that she worked out and had an average/slim body was odd because that was clear from her photos. After a couple weeks, we set a time and place to meet. I arrived at a park near a gazebo she said she would be at. I looked through my windshield, but all I saw was this really tall, obese woman wearing pajamas standing inside.
She was easily 6’4” or 6’5”, certainly taller than I was. I thought maybe she was late, because clearly there was no 5’2” petite female in sight, so I call the girl. I’ll never forget what I saw next. I see the PJ woman’s flip phone light up and play a song I didn’t recognize, and she answered. It was her. She said “I see you,” immediately hung up, and started walking towards my car.
That was the moment I knew I’d wasted an hour of my time driving out to meet a stranger. I hit the lock before she could open door and rolled down the window with a “do I know you?” She said something along the lines of “Yeaaahhhh, I’m a bit taller than I said.” I apologized, said I had to go, and I pulled away. Whatever my type of girl, starting out any relationship on an easily verified lie is a gigantic red flag.
She texted me a minute or so later and told me it was screwed up of me to make her get ready to go out just to leave her hanging. Her version of “getting ready” was putting on old unwashed pajamas. I ended up hanging out with some friends I hadn’t seen in years that happened to live 20 minutes away, so it wasn’t a total loss. Bullet dodged, nonetheless.
48. If The Shoe Fits…
I was taking part in a college "Cinderella" activity where girls put one of their shoes in a pile. A guy would pick a shoe and he'd go out on a date with the girl who the shoe belonged to. My roommates and I all did it as a group and it was supposed to be fun...until the weirdest guy picked my shoe. I honored the activity and went on the date, which was at a bowling alley.
Every time I got up to bowl, he would shout at the top of his lungs like: "THAT'S MY DATE!" He also shot put the bowling ball and probably ruined the lane. Sometimes his throws were so bad they would go down someone else's lane. At one point, he tried to kiss me in front of everyone...It was terrible.
49. When Dating Is Free Therapy
She was a kleptomaniac. I thought she was exaggerating or maybe just went through a tough time. Then she showed me the pile of paperwork. She was on first name terms with the judge because she had been to court so many times. Then she asked me to touch her back. Said she felt super sweaty from the MCAT she'd taken and then showed me how she disposed of her used needles because she was an addict.
Should have noped out sooner, but she was sweet. But yeah, she needed a therapist, not a boyfriend.
50. Just Make A Decision
I matched with a girl on Bumble and we talked over the course of a few weeks. We made plans to meet u one weekend. I texted her the day before to see if we were still on. She didn't reply until the day of. She said that she actually had somewhere to be later in the day, but asked me if I wanted to get coffee before then.
She also asked me if I could pick her up because her car was in the shop. I said yes to both, like a true idiot. She asked me if I knew of any places we could go. I said there was a Starbucks in my area, but she asked me if I knew of any places other than Starbucks. I went on Google, found a neat little local coffee place, and threw that one by her.
She didn't respond for 45 minutes. I ended up shooting her another text asking her how that sounded. She replied back that it sounded good, but the place was closing within the next twenty minutes. I went back to Google and found a different coffee place in her area that didn't close for another two hours. I threw that one by her and then she texted back asking if we could take a raincheck.
I said, "Sure," but didn't have much intention of reaching out to her again. She had already flaked twice before and the fact that she basically ended up wasting most of my afternoon kind of dampened my interest a bit.
51. Putting Out The Wrong Signals
I went out for coffee with a girl. She seemed really nice and cute over texting...Woof. I was wrong. Got there, and she looked vaguely like her photos, but had multiple decayed black teeth, smelled horrendous, and had breath that was so bad that the people in the next state could be hurt by it. She was also really, really...odd. She wasn't mean or rude, but just sort of overall lacked personality, in general.
What really did it was the overall hygiene, though. It was repulsive. At the end of the date we walked to the cars, gave her a hug goodbye, and then she questioned when I was going to kiss her. I tried to be nice and say I don't kiss on the first date, good guy, etc. but she wasn't having it apparently. She stuck her tongue straight into my mouth and said she can't wait for next time when we can have more fun, wink wink.
I sat in my car questioning my life while chewing multiple pieces of gum. It took several rounds of mouthwash to get her taste out of my mouth.
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52. We’re All Confused
It was our third date and we decided to go to a club. It was getting pretty late so we ordered a Lyft to beat the crowds of people trying to exit at the same time. We exited the club and someone pulled my arm hard when we got outside. I turned around and my face went white—a random guy was accusing me of ghosting him and leaving him at a club with the bill.
I told him he had me confused with someone else which only made him more and more upset. He kept reaching and pulling at my arms. My date pushed the random guy away and pulled me closer, which only set him off even more. Security noticed and thought we were causing an issue with the dude. My date tried explaining what was going on and the random dude lunged at me.
I remember I had my taser with me, so I took it out and laid it on him. He fell to the ground, confused. I'm pretty sure he mistook me for someone else, but that was terrifying.
53. Making Small Talk
This would have been in late 2011- early 2012, when Plenty of Fish was still a popular online dating option. This would have been my second (and last) date from online dating. I chatted with this one woman for a few days. She had similar interests and her picture made her seem pretty cute, so I was interested. The day before our date she admitted the picture of her was actually her friend.
She sent me a picture of her from the bridge of her nose up. She had pretty eyes, and I understood the shyness of putting your actual picture out there, so I still went on the date. Her face was…pear shaped to put it bluntly. She was kind of slim, but also chubby in places you don't really think of when you hear "chubby." Anyways, we sat and had coffee, and she only wanted to rant about her mom and little brother, and how unfair it is she had to watch him the previous night.
Considering our online conversations were about video games, music, and TV shows we liked, this was a complete 180 for her. I tried steering the conversation to anything else, but she persisted. We both would have been 21 at the time. I left and told her we weren't a good match, then I deleted my profile later that night. No more for me.
54. Third Wheel
I had been talking to a woman for a couple of weeks and she ran hot and cold. Mostly cold. I was thinking about moving on from her, but then one lonely Saturday night, she called and invited me to a bar for a few drinks. I told myself, why not, and went. when I got there, she was with one of her girlfriends. Her friend was a late 20-something and chatty as anything.
Immediately, I could tell my date was far more interested in her friend’s welfare than in me. It later came out that the friend’s husband was a jealous weirdo. I played along, had a few drinks, and listened to the friend vent her problems, but it was clear I was not part of the night’s festivities. Whatever. It was better than being home alone on a Saturday night. Then, an hour or so later, things got interesting—the weirdo husband showed up.
He charged up to our table, whipped out a camera, and took a picture of all of us. He muttered some vague threat to his wife before leaving. The friend got super upset and decided to go home. My date wanted to walk her out and we went outside to say goodbyes. She walked away and I turned around, thinking finally I got my date to myself.
Then I see she'd already hopped inside her car. She drove off without even a wave goodbye, leaving me all alone. I went back into the bar had a couple more drinks hoping to meet someone, but I suck at bars. I went home an hour later.
55. Food For Thought
I was supposed to pick him up at his Airbnb so we could go out for dinner and drinks. Turns out the place was actually his parents’ house. I thought it was weird that he lied about where he was staying but figured he was just embarrassed so I didn’t make a big deal about it. When I suggested a place I wanted to go for dinner, his response made my hair stand up on end.
He told me his parents made dinner so he wanted to stay there to eat and go out for drinks after. I felt super awkward about having dinner with his family on our first date, but it got worse. He made me a plate of food, had me sit at a table in the garage, and told me he’d be right back. Then he went inside and had dinner with his whole family while I sat alone in the garage.
I wish I could say I noped out of there, but unfortunately I stuck it out for the worst date night of my life.
56. Too Much, Too Soon
I met a guy online about 20 years ago. He was really smart and funny, so I gave him my number. I really enjoyed talking with him. I’m 5’7” and he said he was the same height. I was in my early 20s and he said he was in his early 30s. We decided to meet up on a Saturday morning and go to the flea market which was huge in our area at the time.
When we finally met up, I shook my head in disappointment—he was only 5’4” and in his early 40s, easy. I was mad that he had lied to me, but I really liked him and decided to continue with the date. It was my first time meeting this guy face to face, and he was all over me. Kissing me, hugging me, holding my hand, and I had a difficult time walking around because he was literally attached to my side.
It was just way too much. After the market, he wanted me to come up to his hotel room. When I said no, he was hurt and disappointed. I’m grateful that he didn’t get angry and abusive, but at the time, I couldn’t get away from him fast enough. He quickly moved on.
57. Crazy Cat Lady
I was the bad date: Got super hammered before I got there, talked A LOT about my cat. Invited him in, basically talked him into it. I really wasn't planning on bringing him, so I get undressed and I'm wearing cat underwear, which I know added to my crazy cat lady allure because he commented on them. After finishing some lousy love making, he goes to get dressed and finds my cat sitting next to his cat pee-soaked clothes. Poor guy.
58. Entertain Me
I showed up for a coffee date and about five minutes in, I knew it wasn't going to be a fit. But I figured hey, might as well be polite. After about fifteen minutes of trying to make conversation and getting back one-word responses, I paused. I told her that part of my job was to talk with all sorts of people and that I was struggling to keep the conversation going with her. I then asked if she was okay.
I was legitimately concerned for her because her behavior was so abnormal, and plus, the anecdotal evidence is that I'm a fun and easy date. Her response was chilling: "Oh it's just funny watching you struggle.” I stared at her for a few seconds, then told her she was a terrible person and left. I still shake my head at that one.
59. Getting Back In The Game
This happened to a friend of mine. He had recently broken up with a long-term girl and was looking to “get back out there,” but was too cheap to pay for a dating service so stuck to free ones. He sets up a date with a girl to come over to his place and do some hot tubbing. She shows up and wants some specific kind of drink, I'll say goldschlager, which he didn't have.
So she insists they make a store run. She seemed sketchy, so my buddy is about 50% sure he's going to get robbed, so he tells her to drive and deliberately “forgets” his wallet and phone at home. He had no idea what he was in for. When he gets in her car, there's no passenger seat. She said she has a huge dog so she took the seat out, and he has to sit in the back seat.
The date was late, so the closest store is closed. Rather than go back to his place, she says she knows a store that's open late. He says they're all state stores, they all close the same time...she won't listen and they hit the highway. After a while, he starts to wonder where they're going, and says "Where is this store?" That’s when she screams. She had forgotten he was in the car because he was in the back seat.
My buddy now accepts that she has been drinking for some time. She won't stop or pull over to let him drive, just keeps driving. Turns out the late store is about 30 minutes from his house, and she forgets he was in the car twice more on the trip. They get to the store and it's closed, as expected. This is when she snapped. She gets out anyway and is doing the jerking the locked door thing and yelling "HELLO!" over and over.
My buddy is out of the car watching this as she starts yelling at some sketchy-looking dudes drinking 40s in the parking lot. She starts with "why is this store closed" and quickly escalates to profanity. My buddy takes this as his opportunity and just walks away, doesn't even look back. Now he finds himself 30-minute drive from home, with no wallet or cell phone because he was so smart.
He eventually gets a convenience store clerk to take pity on him and he called his brother to come pick him up. He said he was worried about the girl showing up at his house, but he never heard from her again.
60. A Journey
I started chatting with this girl on Tinder. She was cute and we got on really well. I asked her out for a drink and she said sure. As I was getting ready, she texted to say she was running a bit late. Fair enough—I figured I'd go on time, grab us a table at the bar, and have a cheeky pint to calm my nerves. When I got there, she asked if I could just meet her halfway.
Since it was getting dark, I agreed to meet with her. I was walking and walking but there was no sign of her. She kept texting me updates, telling me which roads to turn on and whatnot, but I was starting to feel a little uncomfortable with it all. Eventually, I came to a house. I hesitantly knocked on the door and some chick in nearly see-through leggings and a matching black top opened the door.
She looked nothing at all like her profile and I felt I'd been catfished. She welcomed me in saying she'd just be a few more minutes and we can go. Me being me, I decided to be polite and play along to the end of the night knowing full well I was never going to talk to her again. We went inside where she then had a screaming competition with her mom and stormed off to her room.
I awkwardly followed, and when I entered her room, I discovered her secret—she was a massive hoarder. Her room was a mess. In the middle of her bed, there was a half-eaten kebab. She invited me to join her and I awkwardly sat on the edge of the bed while she ate it. After chatting for a bit, I mentioned going back out for that drink but she said she wanted to stay in.
When it started to get late, she tried to make several moves on me but I politely turned her down. I excused myself to go to the loo, noped it out the house, and went home. When she realized I'd gone, she texted me a bombardment of nasty messages and threatened to come round mine with a bunch of her mates and hurt me.
I ignored it until she texted me my own address (which I'd never told her) and said she'd see me in a few. Thankfully she never turned up!
61. Off The Deep End
When she was speeding in the rain, driving in the opposite direction of the restaurant, telling me how her parents had her admitted to a psych ward, but she didn’t take any meds because there was nothing wrong with her! I convinced her to stop at a Chinese restaurant instead of a coffee shop because an immediate dinner would have been a shorter evening than a coffee shop on the other side of town.
Afterwards, I told her to take me back to my car because my mother was in town. In the parking lot, she insists that I should not see my mother because I have seen her my whole life, but she and I were just getting to know one another, so I should prioritize my time with her. When I ignored her future calls, she continued to stalk me for months, followed me around town, spied on me running errands, showed up at my house unannounced, knocked on my bedroom window at all hours of the night, left food at my door, left love notes on my windshield, etc.
I was very close to filing a restraining order, but after I physically removed her from my place and my roommate told her I would get a restraining order, she only stalked me on campus.
62. On Thin Ice
I went on what was supposed to be a simple coffee date, but our shopping center was hosting an ice rink that she absolutely wanted to go to. I have poor stability even on solid ground, but I thought maybe a bit of messing around on an ice rink would make her laugh. Nope. Within seconds, I slipped and outright twisted my ankle and wrist.
I needed help being carried out to sit on a bench and try to recover. But here's the kicker—she couldn't care less and continued skating by herself, attracting the attention of another skater. I watched the two of them leave without her even looking back to check on me.
63. Shooting His Shot
So I met a girl on Tinder (I am also a girl). Let’s call her Cecelia. We plan to meet up for coffee. You know, nice slow date, let’s defy the U-Haul stereotype. I get there, and a guy comes up to me. “Hey, are you Kate?” “Yep.” “I’m Brent. Cecelia’s my cousin.” “Oh, could she not make it?” “I was using her pictures. You were talking to me on Tinder.” “Why?” His answer floored me.
“Well, straight girls are so judgmental. So I decided it might be easier to just get a lesbian to turn. You liked me when you thought I was a girl, let’s give it a shot.” Did not give it a shot. Ended up tracking down the real Cecelia through social media and telling her what Brent was doing. Unfortunately, she was not actually a lesbian and I remain chronically single.
My last two dates would not talk about anything but astrology and cryptocurrency, respectively.
64. Dinner And A Show
There was a girl in my IT support training session and she knew so little about computers I was positive she walked into the wrong class and just stuck around. I figured maybe she just wasn’t used to working in an enterprise-level company and maybe she was just out of her element. Either way, I didn’t think she was sticking around so I asked her out.
I later found out that she was an aspiring actress and not a computer professional at all; she just wanted to see if she could play one. The date wasn’t so bad but shortly after the food arrived, her behavior became startlingly weird—started playing with her food. I mean, full-on making sounds while playing with it. I noticed, then made a comment like, “Don’t play with your food,” as a joke.
But she just glared at me then went back to playing with her food. I think I gave her the benefit of the doubt for long enough at that point. She was really attractive which was why I probably looked past everything...but when she started singing to her steak, I kind of just gave up.
65. The One That Got Away
A guy asked me out to lunch. I dressed cute that day. On my lunch break, I met him at his place of employment. We went to the filthy break room/store room where he instructed me to sit on an upside down bucket. He began to prepare a packet of cheesy pasta in the microwave. He served me this tepid glop in a Styrofoam bowl. Then he spent the entire time talking about his ex-girlfriend, who looked like a Renaissance goddess and wrote amazing poetry.
Several years later, I became friends with this woman and told her about this “lunch date” and she was mortified.
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66. Fate Can Be Funny
I finally went on a date with a guy from work who had asked me out about 20 times. It was as awful as expected. He would sit silently staring at my chest then suddenly blurt out some ‘fun fact’ before going back to boob-watching. So, I went to the loo and climbed out the window; except, the worst-case scenario happened—I got stuck. So stuck that the restaurant had to phone for the fire brigade to get me out.
My date had come into the bathroom to watch, but all he did was keep staring at my bum, trying to touch it. The firemen threw him out so he went round the back of the pub (where my top half was sticking out) and tried kissing me there. As my arms were through the hole, I managed to land a right hook on his face.
The firemen made him leave. When I saw him at work the next day, he had a massive black eye and told everyone I had freaked out and attacked him! About three years later, I met my now-husband. One date night, whilst out with friends, my husband was asked about funny moments at his job. Coincidentally, he is a fireman. He told the story of a woman who was trapped in a bathroom window trying to escape a date!
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67. She Didn’t See This One Coming
I was using a dating app and this woman had messaged me first and we had a few great conversations. She was listed at 35. She suggested that we meet up, have a meal and then see where things go. I show up to her place to pick her up and as I am waiting, a 65-year-old woman approaches my car. She introduces herself and I ask her how old she is and she says 35.
I ask to see her ID, she declines and she insists we go get a meal. I politely tell her that the start of any friendship or relationship needs honesty and I would kindly like to know her age as it is obvious she is not 35. Keeps saying she's 35. As we are driving (I am going in circles under the pretext of going to a restaurant) I ask about her life.
She gets interrupted by a phone call she must take as it is from work. She asks for me to pull over to let her talk, I do. She doesn't exit the vehicle. I then hear a conversation that makes it all make sense. She works as phone psychic, and I sit there listening to her faking it to a lady who sounds like she is in need of help, explaining they pay $9.99 the first minute and it goes up from there.
After her call ends she says, "Easy $12." So I resume driving, now headed back to her place which she doesn't realize, and I continue asking her about herself. She drops that she has a son who is 31. I brake as I start laughing and say "So you gave birth at four?" She starts mumbling about how she misspoke but I pulled up in front of her building and politely asked her to exit the vehicle as dishonesty is a deal breaker.
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68. Ah, Young Love
One time in the eighth grade, I finally got the courage to ask this girl out. She just so happened to be the friend of my best friend’s current girlfriend, so we decided to make it a double date. During the movie, everything was going as planned. I sat by her while my friend sat with his girlfriend. Then we saw a couple of her girlfriends walk into the theater.
They happened to see the girl I was with right away. She then motioned with her hand for her friends to come over there. When her friends got to where we were sitting, the girl I asked out turned to me and asked, "Can you scoot down a seat so I can sit next to my friends?" I said sure, so I got up, and just walked out of the theater.
69. Game Night Gone Wrong
An alleged friend told me her co-worker and I would be great together and wanted to do a double date at a festival with her and her husband. The date suggested he and I meet up the night before to get to know each other and I suggested a gaming bar I'd wanted to try. Date time arrives and he's not there. He finally shows up and tells me he had to stop home to let the dogs out so they don't poop all over the floor.
He then proceeds to show me a picture of a floor covered in dog poop and says, “Guess it didn't work.” He is still wearing his work clothes. It has been three hours since work ended and he went home to deal with the dogs but didn't change. He proceeds to eat the rest of the charcuterie plate I ordered by himself and then orders wings for himself.
We decide to check out a game since I have now paid for more game time. He wants a mall madness game that is not designed for two people. We settle on a playable game. It's not great. As we are wrapping up, he tells me the last date he took here hooked up with him in the parking lot. He then stares at me expectantly. I tell him that's not going to happen.
I tell my friend I'm skipping the festival. He's shocked and thought we had a spark.
70. No One Had Fun That Day
The girl was totally normal, nice, and well-mannered. It was the circumstances that made it awful. We decided to meet at this bar/grill with a big outdoor patio in the late afternoon one weekend. We got there and the place was PACKED, so the hostess sat us at a small table for two. As soon as we sat, we heard an older woman say my date’s name in kind of a shocked tone.
My date turned her head and her face dropped. It was her MOM! Her mother just happened to be there getting some drinks with friends, so we had to spend our whole first date making chit-chat and sipping our drinks with her mother about five feet away.
71. All Over The Shop
He was picking me up and texted me "here" a little early, so he had plenty of time to do this before I got down to his car. But no, he waited until I opened the door and there were about a dozen right-wing magazines on the passenger's seat. He said, "Hope you're not some crazy liberal! Don’t mind these mags" and then brushed them onto the floor.
It was super awkward and cringy. It was my first date since a rough breakup and the rest of it was just as bad if not worse. I ended up crying in the bathroom halfway through. Also, he picked me up in a Prius—which like great car, save gas and what not, but also like the antithesis of what you would expect from someone whose first comment to me was “hope you’re not some crazy liberal.”
For the rest of the date he just kind of ragged on me, like he asked me my hobbies and I said scuba diving, and he went on and on about how that’s bad for you and he free dives soooo far down and can hold his breath soooo long that he doesn't need air on his back; he's in such good shape! I was like okay. He asked me if I cook and I told him I'm a bad cook but I don’t care because I'm not a picky eater at all.
He went off about how his mom was such a good cook and "southern values" and how it’s so unfortunate I can't cook. He didn’t outright say “as a woman” but still comparing me to his mom a bunch and using phrase "southern values" alluded to that. Then I think he could tell we had NOTHING in common so he asked if I would mind if his friends would join us.
I was like sure, honestly excited because I figured they had to be better than him and assumed they would be our age, in their 20s. They were 60+ year old fishermen. Honestly, though, that was the highlight of the date. They were kind of cool, and it made sense to me he did not have friends our age.
72. Red Hot Love
I once invited a girl I liked a lot to see a movie and she agreed. We chatted about this and that before the movie started and out of the blue, she mentioned her boyfriend. I kept talking as if it was no issue, but halfway through the movie, I excused myself to the bathroom. I walked out and planned to never see her again.
She called me about a week later saying had lied about the boyfriend because she was nervous. I liked her so much that I decided I would give her another chance. On the second date, it didn't get any better. She told me she was a volunteer firefighter which was cool. But the only thing she was interested in was... fire. "Have you ever seen a house burn? It's so beautiful!"
Fire this, fire that on and on through the evening. Every time I tried to draw the topic away from fires, she found a way to come back to it. Needless to say, I never called her again!
73. A Family Affair
I showed up and her best friend was there. I hadn’t been warned she was coming with us. Then her brother showed up. Then her dad showed up. Then her mom and her three of her cousins aged 3-5 showed up. That was the point I excused myself to go to the bathroom. THANKFULLY this is one of those places where the employees will sneak you out if you’re having a bad date and need an out, and apparently I’m the first guy they snuck out at that point.
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74. Did It Hurt When You Fell… From Bed?
We were getting it on and he launched me out of bed. My head broke the fall. I kept blacking out so he took me to the ER. As I was sitting in bed with a neck brace on, awaiting tests, he asked if he could see me again. I just stared at him. Twelve hours later, I was released with a severe concussion. The doctor asked me to take a month off of work.
I couldn’t do that so she lowered it to a week if I agreed to sleep during most of it. So, for seven days, I was on medication that knocked me completely out. I would wake up long enough to eat, drink some water, pee, and take more medication. The adult cuddling wasn’t even that good… and no, I never saw him again.
75. Fancy Meeting You Here
Before our first-ever date, which he told me he wanted to plan, I’d told him I had been vegetarian for a few years now and as long as where we went had vegetarian options, I didn’t mind where it was. He brought me to a steakhouse. Said he’d forgotten I’d said that. I ended up just having fries the whole night. Points to him, he did seem like he had actually forgotten and the conversation was good so I agreed to a second date.
Now, I had also told him I was caffeine intolerant—couldn’t have any coffee, Coke, most teas etc. And where did we go? To the university coffee stand. I left to go to my archaeology class and my desk buddy tells me we are getting a new tutor because our first one got sick and couldn’t see the rest of the semester through. Guess who our new tutor was? Mr. Steakhouse and Coffee Stand Guy.
I maintain to this day that it was worth it all just for the look on his face when he walked into class. I wish I was making this up.
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76. An Unsettling Turn Of Events
I met a girl online who was beautiful, fit, and smart, but a little older; only by about five years. She was a dentist and we had an awesome date. She came over and we did the deed—she scratched up my back and all, but whatever, it was great. That morning, I woke up to the sound of plates breaking. I ran downstairs and saw her throwing out all my plates into the trashcan.
I calmly asked her why she was doing that and she said I deserved better plates. OK, I suppose so. Then she asked to go upstairs and cuddle. That's when things got scary. She started whispering to me about how she lost her ability to practice dentistry and that she was not what she seemed. I laughed a little and started to get nervous. When I asked her if she was OK, She ran off to my bathroom and locked the door.
At that point, I was pretty terrified she was going to either use my razor on herself or on me. I heard the sound of canisters being emptied out and nervously asked what she was doing. She came out and says she made a mistake. She was married and has a child but she was not allowed to see her kid or stay at the house. At that point, I realized I was dealing with someone ill.
I told her to come downstairs and I'd cook her some eggs. I had no plates anymore, so I offered to take her out for a quick sandwich. We headed over to the place and not a single word was exchanged. I picked up both sandwiches and we ate them on a bench outside. She said thank you and called me cute, then left me there. She just walked away without a word and I didn’t hear from her again.
77. Moving Fast
Drove 50 minutes to her small town to watch a movie. Turns out she meant at her place, and it was a sequel to a trilogy I had never started. She was pretty awkward, which was fine but then she started REALLY over sharing saying she was a crack baby and telling me all her trauma. That was the point I knew it was a mistake, considering she had fibbed her way into the date.
By the end of the night she was telling me she loved me. I left shortly after that and I let her down over text once I was home. Cherry on top: she got pregnant three months later from her boyfriend of five months.
78. The Art Of Pitching Woo
I was 10 years old and had a huge crush on my best guy friend who probably still thought girls had cooties. Being a hopeless romantic, I decided what better date to go on than dinner and a movie. My mother, as our chaperone, brought us to Olive Garden where I excused myself to the bathroom and proceeded to change into the only dress I owned.
Then we went out to the movies where I insisted that my mother and sister sit in a different row from us and, faking the damsel in distress, asked him if he would hold my hand if I got scared. Even better, when we dropped him off at home that night, to his horror, I kissed him on the cheek in front of his mom and older sister.
I then spent the next few YEARS being ridiculed about the whole event while his sister told the story to all our friends every chance she got. Needless to say, I embarrassed myself pretty well, and probably scarred this poor boy for most of his prepubescent life.
79. Kind To Be Cruel
I waited on the park bench next to a girl for about 30 minutes after the agreed-upon time I was supposed to meet my date. Turns out I was sitting next to my date the entire time, I just didn’t recognize her because she was at least 200 lbs bigger than any of her pictures with no similarities. Turns out her much more attractive friend was trying to help her out by making a Tinder profile, using her own pictures, doing the matching and flirting, and then letting her less attractive friend actually do the meetings. She should not have tried to help.
80. Jokes On Him
I showed up at the pub and he looked only vaguely like his pictures. I thought well, I'm not really attracted to him, but maybe he has a good personality. As we went deeper into the date, I got my answer. He started asking me questions about my interests and then dissecting and belittling my answers. The one that I remember the most was, "What kind of movies do you like?"
I replied that I like comedies, to which he responded, "Oh, I only like documentaries because I actually can learn something. I surround myself with friends who are funny so that's where I get my humor." After several interactions like that, I just went home. I was surprised when he texted me asking if I wanted to hang out again. He does know how to be funny after all.
81. Joking Around
I went to this guy’s house to play Magic after meeting him at my local store a couple times. I excused myself to pee. It took a very dark turn. As I was peeing, he stood outside of the bathroom door and did an awful impression of the Joker laugh while saying he’s been waiting for someone like me and other extremely creepy phrases about how I am “perfect for him.”
The post peeing bathroom exit was so absolutely awkward. Riddled with me saying several different versions of “Oh wow, that was a great Joker impression haha” and him continuing to speak like the Joker. It was the longest, most tense, fearful walk down the stairs. I left shortly after that. It still haunts me.
82. A Whirlwind Romance
I excitedly met up with this girl at a bar and the first thing she told me is that my hair is gross. I take very good care of my hair; she just doesn’t like long hair on dudes. We got the pleasantries out of the way and then she went on to brag about how she'd been with several guys who were over six feet (I’m 5’8"). She then asked me to send her $30 because “These nails didn’t do themselves.”
But that's not even the worst part. Continuing on, she started roasting me for living with my family even though she also lived with her family. At the end of the date, she asked me to sit in her car with her. I agreed and we talked for a bit. It got a bit too political, which I didn't like, but it was better than hearing about her escapades. After a while, she told me that she was leaving because some other guy had just arrived to pick her up.
83. Only One Woman For Me
He said how he missed his mom and started crying because the music reminded him of her. She's alive and all. Just wasn't there at the restaurant with us.
84. Three’s A Crowd
I once went with a larger group of friends to an outdoor movie festival that was happening in a remote place. You could only get there by boat, but it still attracted quite a number of people. The options were camping or a super expensive hotel. I was in college, so we camped. The place also had an outside bar and restaurant.
I was sharing my tent with my then-girlfriend and one of my exes had tagged along because we were on good terms and she was part of my group of friends. Fast forward to the first evening of the festival and we were grabbing dinner at the venue. I bumped into another of my exes. Being the polite person that I am, I said hi and asked her how she was doing.
She later sat down at the same table. Things were beginning to get awkward for me at that point. As I was finishing my food, guess what? Another ex showed up with her current boyfriend and sat down at the table. Mind you, at that moment, there was my current girlfriend and three of my exes sitting at the same table, along with some other people.
One of my friends decided to make things extra weird by very loudly pointing out the situation and ensuring everyone there knew who everyone else was. Needless to say, I had a freshly minted ex by the time the night was over.
85. Tell Me How You Really Feel
When she live-tweeted the date and said she didn’t want to be there…at the beginning of the date.
86. Mistake Number One
I talked to this guy on OkCupid for about three or four days. I learned an important lesson after I made the mistake of telling him where I work. One night, he told me that he was going to the casino with his friends. In the morning, he said that he won some money and used it to buy me a gift because he really felt that this was going to be something special.
I told him I was uncomfortable with him buying me a gift as we had only been chatting with each other for a few days. But he didn't want to hear it—he replied that he was going to take the next bus and get off at the stop near my work. He told me to meet him there if I wanted the gift and if I felt the same way. I didn’t respond.
I also didn’t show up. When I left work for the day hours later, I saw him sitting at the bus stop with a brown paper bag in his hands. I blocked him and changed jobs. It was just a fast-food part-time thing during college, so I was easily able to find something else. I didn’t feel safe working there anymore.
87. Dress The Part
That time when I walked into the restaurant where I was meeting a “Dr.” was the worst date I’ve ever had. I met him online, and he was there wearing a white lab coat….to dinner…our first (and last) date.
88. Memory Of A Goldfish
I’d been messaging a girl on Tinder for a couple of weeks. We even spoke on the phone some nights and she seemed pretty cool. We organized a date to check out a food market in the city and I offered to pick her up from her place. I let her know when I was on my way, but when I got there and let her know I was outside, there was no answer.
She lived in a gated apartment block so all I could really do was call and text. I must have waited out there for about 20 minutes trying to let her know I had arrived, but still no response. I went to grab myself a burrito near her place and she called me later with an update that made my blood boil—she told me she’d "forgotten about our date"… even though I literally called her like 30 minutes beforehand to confirm.
Anyway, she begged me to come back, and stupidly I obliged. By the time we went out, most places to eat were closed and she didn’t want to go to any bars or anything. She barely made an effort to engage in conversation and was just scrolling on her phone while we drove around. In the end, we decided to just call it a night.
89. From A Yes To A No
When he asked me out and I said yes, he then asked if I’d like to go to dinner and what kind of food I liked. I said anything but sushi. He took me to a sushi place. Said he thought he’d be able to change my mind.
90. A Sly Twist Of Fate
This was the first woman I went on a date with after getting out of the army. She pretended to twist her ankle in the restroom as the bill came out. She then had me carry her, fireman style, outside to her car where she tried to convince me she couldn't drive because it put pressure on her foot (she was trying to get me to invite her back to my place, I assume).
When I asked her if any family members could pick her up, she said no. I was standing outside the driver's door at the time and she asked if I could just look inside to see if her foot looked normal. My naïve self just leaned in and that was a big mistake–she tried to kiss me. I pulled back saying I wasn't feeling that kind of connection.
She called me a terrible person, then burned out of the parking lot. She later proceeded to blow up my phone saying how sorry she was and that we were soulmates.
91. A Real Winner
I suggested a Tinder date meet me at the Hirshhorn Museum in DC. He showed up, said, "I hate art" and then touched every single piece of it until a guard saw.
92. He Tried So Hard And Yet…
I convinced a girl who I was crazy about to go out on a date with me. I knew I had to make it count. We lived by the ocean and she had dropped the hint that she had never been out on the pier at our local beach. Challenge accepted. I nervously drove her down to the beach and we proceeded to slowly walk out on the pier together.
She seemed hesitant from the beginning. We stopped short of the end and I leaned against the railing over the water while she stood back a bit from the edge. She didn’t really seem into it at all. Awkwardly I said, “This is a great view, huh?” Just then, two pigeons flew up and landed at our feet. “Sweet, chicks dig birds,” I thought to myself.
To my horror, the birds began to make passionate pigeon love in front of us while neither of us spoke. I had never witnessed such athletic passion. I quickly scanned around and saw a couple holding roses on the other side of the pier. “Awesome, they look romantic, chicks dig romance,” I thought to myself. We quickly walked away stood next to the happy couple.
The man and woman were holding each other and both holding roses but something seemed off. I glanced up and noticed that both were sobbing, the girl I was with noticed too. As we were both looking, the couple took their roses and cast them into the sea. I had posted us up next to a funeral, some kind of sea burial.
Between animal lovemaking and funerary rites, I had executed one of the worst dates of all time. Just as I had accepted my failure, my date started getting fidgety. Based on her body language and her expression it dawned that she hadn't told me about the pier as a hint but because she was terrified of it. Turns out she had a fear of heights and the ocean.
93. Disappearing Act
We matched on Bumble and hit it off. She asked if I wanted to talk on Snapchat instead. I said sure. We had a good time and I asked if she wanted to go out for dinner that week. She said yes, so I suggested a place between our towns so neither of us would have to drive the full distance. She said she wanted to be closer to her house, and that she knew a nice, low-key Italian place in her town.
I said okay, and we continued talking until the date. We were sending pictures on Snapchat, so there was no catfishing on either of our ends. We knew we were the people in our profile pictures. So the day comes up and I drive the 55 minutes to her town. We meet up at the restaurant, everything is smiles and laughs. Sit at the table, the waiter asks what we’d like to drink.
I get a water, she says she’ll have the same. I ask her what’s good on the menu, because she said she’s been here before. She names off some things, tells me what she plans on ordering. I take one of her suggestions so we could spend time talking instead of me looking over a menu she’s already familiar with. I asked her how her week went, she told me about how much of a hassle work was.
She worked in cyber-security or something like that, and I asked how she got into that line of work. She started talking about her major and where she studied. She asked me about school and what I studied, I told her and said I was now in grad school full time while working part-time as a security guard at night. One of us made a joke about how we both do security in some way, and we both laughed. I could have had no idea what was coming.
The waiter came over with our drinks and asked if we were ready to order. We both ordered, and he walked away. IMMEDIATELY she says she needs to run to the toilet really quickly. She grabs her bag and coat and leaves the restaurant. No urgency to it. No shame. Nothing in her voice to suggest she was having a bad time. It was all very casual.
Now, I have both a friend and a family member who refuse to use public restrooms, so my mind immediately said “Oh, she wanted to be close to home in case she had to use the toilet. That makes sense.” No big deal. After about 15 minutes, the waiter comes over and delivers our dinners. I say my date had to step out but should be back soon.
I wait about ten more minutes and start eating, because the food was getting cold. I text her something like “Hey, is everything okay?” She doesn’t respond for another ten or so minutes. When she does: “Yeah!” I text her, “Are you coming back? The food’s getting cold lol.” Her response still shocks me. She says “Nope!” One-word responses, with exclamation marks.
At this point, I’m confused. I feel like I didn’t stress this enough: We ordered our food and then she IMMEDIATELY got up and left. It wasn’t that we ordered and I said something that made her uncomfortable. She said she had to use the toilet before our waiter had walked even five steps from the table. So not only am I confused at this point, but I’m kind of angry.
I drove almost an hour out, and now I was going to have to pay for an uneaten meal? So I stewed over a text for a while, trying to come off as, well, not upset. I texted: “Oh…okay? If something suddenly came up we can reschedule? I don’t know why you wouldn’t just say so though?” And she said, “No, nothing came up. I just didn’t feel a spark.”
Now, I’m sure we’ve all been to a restaurant before. It doesn’t take long for a waiter to bring you your drinks and ask if you’re ready to order. Maybe 10 minutes, max? So we talked for 10 minutes, at most, with the bulk of that time being her talking about her work—mostly gossiping about co-workers that I don’t know. Then she deliberately ordered food and left.
You’d think if she wanted to leave she’d not have ordered first? Anyway, I finished my dinner, the waiter came over and asked if I was done with my plate. I said he could take the other one too because my date had walked out. He said, “Before the food showed up? Rough.” I said, “Actually, she left right after you took the order.” He kind of laughed and said, “Darn, sorry man. You want a drink?”
I said I shouldn’t. He said it was on the house. So I said sure, thank you. He got me a drink and came back later with the bill. I said the second meal wasn’t on there, and he said, “You’ve had a tough night, don’t worry about it.” So I tipped him $16, which was what I estimated the cost of her meal to be. Never heard from the girl again. No idea what that was all about.
94. It Could Have Gone Better
I met this girl on the Internet and she seemed really nice and down-to-earth. We had a lot in common including our hobbies and politics and stuff like that, so I thought we might hit it off. We agreed to meet up in person at a coffee place. Now, bear in mind that I'm not super attractive and up to this point, she hadn't seen any pictures of me.
Instead, we had pre-arranged recognition signals. She walked in the door and I spotted her by her clothing instantly, so started waving. She got this sort of uncertain look on her face, then walked over and said, "Sam?" and when I say yes, she just said, "Haha...NO."
95. This Is A Girl Who Can Multi-Task
I was 18, a girl sent me a message on MSN saying she got my details from my friend and wanted to go on a date with me. I asked my friend and he said she was hot, so after talking a bit I agreed to a date. I had seen a photo and she was attractive. I turned up at the cafe for the date. It all went wrong instantly. I was approached by some girl I'd never seen with a baby.
She then told me she was the girl, even though she looked nothing like her photo. She explained she thought I'd never go for someone who looked like her (she was right). But that wasn’t all. She then left her baby with me while she went to the toilet quickly. Alarm bells started to ring after 15 minutes. I asked a waitress to check on her.
When the waitress came back, she told me news that made my blood run cold. She said no one was in there. I looked around the cafe and she was gone. I hadn't noticed her leaving. I didn't have any of her contact details and smartphones were not a thing so I didn't have internet access. I phoned my friend and got him to attempt to contact her on MSN.
After telling him what happened he was surprised and had no idea, apparently he also thought her pictures were the real her. Another 20 minutes went by and I was scared so I asked the waitress for help. Thankfully she was able to help and called the authorities. They showed up and I explained what happened. I didn't know anything about this girl so I couldn't really help them.
They said if she contacted me to get her to contact them. I left and walked towards my car, and in so doing I went past another cafe about six shops down. I couldn’t believe what I saw. There she was with a different guy. I went back to the officers and got them to take her baby in while I watched through the window outside and waved when she looked up. Turns out I was the babysitter for her real date.
96. A Relaxing Vacation
I met this guy. We vibed right away and started hooking up within a day or two. This guy swept me off my feet and I couldn't help but think, “Yes! FINALLY, a real man.” Then, one day he said to me: “I know this house we could go stay at for the weekend if you’re interested.” Sounds great, right? But then we got there and he said he forgot his key...so he proceeded to get a crowbar.
That freaked me out, so I asked him to explain exactly whose house we were at. He assured me that it was his dad’s summer house and he definitely had permission to use it. I ignored my gut instinct and decided I was probably just freaking out for nothing and overreacting. We stayed there for about four days, with no more issues.
I slept in the master bedroom, showered there, made food in the kitchen, the works. When we left, this guy said, “Look what I got.” He proceeded to show me jewelry and some credit cards from the house. I was starting to truly panic now. As naïve as I was, I still thought it was his dad’s house and he was just having a rebellious moment.
And that’s when he fessed up. I realized that I’d just helped him burglarize this home. It wasn't even his dad's house; it was his mom's ex-boyfriend’s house, and let me tell you—they did NOT give him permission to be there. His stepdad even had a restraining order on him for a similar incident a few years before.
So fast forward a few weeks—I got pulled over and snatched out of my car for having been involved in this whole thing because these people had rightfully pressed charges. I ended up narrowly avoiding doing serious time.
97. Emily Post’s Long-Lost Brother
While perusing the menu, he asked what I was going to get. I said "Um, I'm thinking about…" and he cut me off to say "They don't have UM here." I chuckled and continued "So I think I'll have the uh chicken." He responded seriously with a raised voice, "They don't have UH CHICKEN here either" and shook his head like I was annoying. I just stared at him for a minute.
98. Cats, Cats, Everywhere There’s Cats
I met this girl online. She seemed nice, geeky, and into a lot of the same nerd stuff that I was. She was cute in her photos too. She dodged me several times about going on an actual date, but finally, we managed to set something up. She wanted me to come to her house so she could make us dinner and watch a movie together. We were both introverts, so that was fine by me.
She said she lived in Houston, but it was actually over an hour outside of it. When I got to her 'house', my jaw dropped—it was actually a trailer in the middle of the woods on a wooded lot full of trash. Turns out, they didn't have trash service, so she basically just threw it outside. At first, I thought I was seeing cats everywhere, but it turned out to be cats mixed in with a few massive rats.
Still, I'd driven an hour plus, and I was already there, so I climbed up the decrepit deck and knocked on the door. When she opened it, the smell of cat urine poured out of the trailer and invaded my nostrils. When I got inside, there were more cats everywhere. Orange cats, brown cats, old cats, young cats. Cats everywhere.
Her mom was "cooking dinner" for us, which was frozen microwaved dinner. This girl then dragged me to her room and attacked me like an animal in heat. I told her I had to go to the restroom but it was covered in cat waste and litter. Just box after box, in the shower and everything. I couldn't do it. I went and told her I’d forgotten flowers in my car and drove away as fast as I could.
99. Oh, Those Summer Nights
A couple of years ago I went on a date with this girl who I had a crush on in my college math class. I was too scared to ask her out and didn’t do so until one summer day when she hit me up on Snapchat asking about some tea places that I knew of. I told her some places, then I shot my shot, saying we should check one out together.
She agreed. I picked her up and we went to the tea place. We had a really nice time and even played Jenga. I didn’t want the date to end, so I took her to a lighthouse on the beach. We got to know each other so well and had nothing but a great time laughing the night away. Night eventually came and she had to go home, but we planned on hanging out again soon.
A week or two later, I woke up and checked my Instagram. The first post I saw made my blood run cold. It was her with another dude at the same beach holding on to each other. Mind you, she told me she was single and not talking to anyone. I was heartbroken even though we only hung out that one time.
100. Bait And Switch
When she responded to a “Hi” on Tinder with something like “hey cutie, want to come to my parents’ house?” We chatted for a bit, and according to her she wasn’t looking for anything serious but she wanted me to pick her up, take her out to dinner, and maybe get it on afterwards. Very transactional, which kind of stung but whatever she was hot.
I looked up the address she gave me. When I read it, I got a small, dark feeling. I was surprised to find a neighborhood I did some work in, and that the house was one I knew was for sale. Specifically, the owner passed and it was being gutted to be resold by his kids. At this point I was 100% convinced this was a scam, but somewhat curious, I decided to drive by and see if anyone was there.
I texted her I was coming, but in a different type of car. It was a really expensive neighborhood on a sea-cliff, and it felt like an adventure. I took my work truck. I drove by and some huge dude comes out of the house, stares at my truck, and goes back in. I could see other people inside. I noped out of there super fast. Pretty convinced it was a phishing scam to mug me, or a prank. Didn’t feel like finding out.
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