July 8, 2022 | Eul Basa

Disaster Dates: These Horror Stories Made Romance Turn Rancid

It seems that with the advent of online dating, stories of ridiculously bad dates have been on the rise. We’ve probably all been misled by appearances at some point, online or otherwise, but there are some stories that take it to the extreme. From strange venues to physical injury, these Redditors share their most outrageous dating moments.

1. Ok, Happy Gilmore

My wife told me about a date she went on once with a guy who turned up in shorts and flip flops on a rainy day in November. When she asked him if he was cold, he said "Nope, I have no feeling in my feet. Look!" He proceeded to stab himself in the foot with his umbrella while repeatedly asking her if she "wanted a go."

Disastrous Dates Facts Wikimedia Commons

2. Three’s a Crowd

Went to pick a girl up at her house after meeting her on a dating website. She seemed significantly larger than her photo, but only in the lower abdominal region. This is when I realized that she had failed to mention that she was pregnant.

Alcibiades FactsShutterstock

3. Argh, Matey

I was 16 years old when I scored a date with an 18-year-old girl. I really, really liked this girl, so of course I was extremely nervous. It was also my first date ever. I took her out to eat, and then we went to see the second Mummy movie. Everything was going great, I even had my arm around her and all that jazz.

Then, during the pigmy chase scene, one of those dudes popped up and made me jump. My arm was still around her—and somehow, my finger went straight into her eye. In fact, I had not only poked, but had actually scratched this poor girl’s eye. Our date ended because she had to go to the ER. But that wasn't even the worst part.

To make matters even more humiliating for me, she then had to wear an eye patch for weeks. So, during the first date I ever went on, I turned the girl into a pirate.

Scandalous Historical FactsShutterstock

4. Method Actor?

I went out with a guy for a pizza date. Or so I thought. As we were sitting eating our pizza, he suddenly put on a clown nose out of nowhere, and then just kept eating. I asked him if there was an explanation to that, and he said he was "just trying out his new nose." Then he started jazz scatting like he was Ella Fitzgerald. For two hours, he was just jammin’ to himself in a pizza place with a clown nose.

I didn’t want to leave because I was his ride back to the train station, and because he had traveled pretty far to see me. Eventually, I drove him back to the train station. He didn’t get out of my car. I asked him why, and he said, “I’m thinking.” Then he leaned in like he was going to kiss me—but instead rubbed his face on mine like a cat, licked my cheek, and left. Of all of my bad dates, none have ever left me more confused than that one.

Disastrous Dates FactsNeedpix

5. Ballin’

A guy I worked with kept asking me out, but I continuously said no. After about a year, I started to feel bad for the guy and finally said yes to a date. He asked me to lunch, so I figured it could be a quick, easy "date." He picked me up. Then he took me to Wendy's. Then he made me order off the dollar menu. I also had a limit of two items.

After a very quiet lunch, during which he hunkered over his chicken nuggets like I would steal them, he said he needed to stop at Walmart. We went in and he headed to the lotion section. He then grabbed two scented lotions and asked which one I liked better. Trying to be nice, I picked one. He responded with one of the most horrifying sentences I've ever heard.

"Great! I'll use this for your massage!" Luckily, I had to work in two hours, so I had an excuse to tell him the massage would have to wait. I spent the next three months trying to avoid him until he quit.

Stopped Caring FactsShutterstock

6. Wrong Answer

I had a guy take me to a Beer n' Christ show. He was an extremely strict Catholic and thought I could benefit from letting Christ into my cold, cold, cold, Jewish heart. So I went. I was open-minded; I'm only half-Jewish and have always been interested in other religions. It was going okay...until the priest told us a hypothetical tale of a brother who is paralyzed.

He asked, "How many of you here would purchase stem cells if they could allow your brother to walk again?" My hand shot up. I looked around the room... and realized I’d answered incorrectly. No other hands. Everybody was staring at me, including my date and the priest. I was ‘blessed out’ like nobody's business and was told I was an embarrassment to my date.

Dumbest Things Heard factsShutterstock

7. Cruel and Unusual Punishment

A girl I had just met asked me out to dinner. We ended up at this little Italian place, because she said she knew someone who worked there. When our waiter arrived, he appeared visibly shaken, and was stuttering. She introduced him to me as the friend that she’d mentioned before. I could see right away that something was very wrong. 

The guy obviously had a thing for her from the way he cringed when she introduced me as her date. She then bugged him for special orders and asked if we could get our meals free. He really seemed upset, but he gave her the "anything for you" look and agreed to help us out. All the same, I declined and paid for my own meal.

I felt really bad for the guy. I could see his torment at watching this girl date someone else. She was very attractive and very friendly, and I assumed he had just been friend-zoned. I hung out with her a few more times, but backed off of the romantic part. Then I found out the whole truth: The guy from the restaurant was her ex-boyfriend of 3 years, who she had just dumped a few days before our date.

Hate Someone FactsShutterstock

8. Dodged a Brainwash

On my first date with a guy I met on an Internet dating site, he took me to the Scientology museum in London. I thought it was a unique date, and that it would make it easy to find things to talk about or laugh about. Nope. He proceeded to read every single piece of writing on every single exhibit. He also asked the attendant very probing questions about how one goes about joining Scientology, visibly sweating throughout the conversation.

Once we were done there, we went for a glass of wine and he told me he used to do a lot of hard substances. I was out of there like a shot.

UFOs factsWikimedia Commons, Scientology Media

9. You Stole My Heart

I went out to the movies with a girl on Valentine’s day, and it was going well. Afterward, as we were getting ready to call it a night, she wanted to go for a quick visit to a gift shop. We went to a nice one nearby, and I bought a few greeting cards while she just browsed. When it came time to pay, I paid for my cards and was getting ready to leave.

The cashier asked me if I wanted to buy anything else, and I said no. Then he asked my date, "Is there something you want to buy, Miss?" I looked back and forth between them, confused. She said no, but he asked again, "Are you sure?" She said she was sure. The cashier got this really intent look on his face—and suddenly, everything unraveled. 

The cashier shouted "NOW!" and 5 of the staff surrounded us like a scene from a movie. The girl apparently was a kleptomaniac and had stuffed lots of gifts in her pants and bra. They had electronic surveillance and had caught it all on tape. The cashier threatened to call the authorities on the girl, but told me I could leave, as he could see I had no idea what was going on.

I decided to help the girl out and ended up buying all the stuff she had stolen to get her out of getting busted and her parents finding out.

Retail Workers Disturbing Moments FactsShutterstock

10. Cruel Intentions

So I went on a couple of dates with this girl, and she was giving me some signs that she was ready to get a little physical. So I leaned in close and tried to kiss her,  only to have her turn her face away from me. Stunned, I ended up going home and thinking it was over between us, but later on, she contacted me and wanted to go out again. I decided to go for it.

Again, after getting some heavy hints from her, I leaned in to kiss her—and she pushed me away again. So then I just flat-out asked what was going on. She straight-up tells me "I'm dating you so I can feel desirable, but I'm not attracted to you." She called me the next day wanting to go out, and I told her I wasn’t dating people who made me feel undesirable, then hung up.

Flirting Or Just Being Friendly? These People Couldn't Tell The DifferenceShutterstock

11. Let Down

I met this guy online and he kept bugging me to take me out to dinner. I finally agreed and he said he wanted to take me "somewhere nice." We agreed to meet in a well-lit grocery store parking lot and then ride to the restaurant in his car. It was cool out, so I had put on a dress and tights and high-heeled boots. He pulled up in a Mercedes, and I suddenly wondered if I was dressed well enough for wherever we were going.

Now, I don't know about any of you, but when I hear "somewhere nice," it means a place that involves wait staff and tablecloths. We did the greetings and I got in his car and he drove us across the parking lot – to the Taco Bell drive-thru. I am not joking. I texted my teenage daughter from his car and she told me that things like that only happen in the movies. Needless to say, there was no second date.

Most Metal Things They’ve Seen factsFlickr, Mike Baird

12. Keep Your Pants on

My freshman year of college, I met this amazing, cute guy on the bus. We talked until I had to get off. A few weeks later, he came up as a suggested friend on Facebook. I added him, and we decided to meet up for tea. He showed up dressed in a full suit, and then proceeded to take me to a computer lab on campus...where he made us tea in a microwave.

He talked the entire time about how he was a nude model, and therefore was really good at sitting still?? He then demonstrated this by sitting still without moving for about 30 minutes, not looking at me, as I struggled to talk to him. Two weeks later, I cut through a building on campus and saw nude paintings of him. We never went out again.

Strangest Date FactsShutterstock

13. Hallelujah

In University, I was interested in a gorgeous woman in one of my classes. Every time I saw her, I’d flirt shamelessly, so I was elated when she asked me out. She said we were going to see some live music. I went. I was in for a nasty surprise. She had taken me to a born again Christian conversion ambush group. They were singing songs though, so I stayed until the end.

Disastrous Dates FactsWikimedia Commons

14. Better Than a Toothache! Or…Not

A guy I had met three days previously offered to pick me up so we could hang out. I was cool with that, until he ended up dragging me around on errands. We even went to his dentist appointment. When I said I wanted to go home, he said he'd give me a ride, but only in exchange for oral favors. I got out right there and walked to a bus stop.

“I Called It” Moment FactsShutterstock

15. A Dangerous Game

I met a girl on OkCupid and took her out to dinner. She seemed a little odd, but overall nice, and the conversation was going well. We both liked video games, so I invited her over to my place after dinner for some Xbox action. It went downhill very fast. She then proceeded to drink all my liquor and take all my leftover pain medication from a work injury I had suffered a few months prior.

Then, when I asked her to leave, she started unplugging all my stuff and calling me names like "Brian" and "Todd" and going on about how she doesn't like it when people hit her. I told her I was taking her home and ended up having to physically drag her to my car with her kicking and screaming the whole way there.

She then tried to get out of my car while we were on the highway, but thankfully I had the sense to lock the doors and she was too drunk to realize it. She got angry and started hitting me while I was driving on the highway. I finally got her home, got her through her front door, and fled. On my way back to my car, her iPhone hit me in the back of the head.

I drove home bleeding. She called me the next day from a number I didn't recognize asking how our date went and if I knew where her phone was. I laughed and hung up.

Hortense Mancini FactsShutterstock

16. Not as Previewed

When I was about 20, I agreed to a date with a guy who had described himself as "nearly six foot, athletic, late 30s." I met him outside my friend’s bar. He was just slightly taller than me (I was 5 ft 5 inches), skinny, had grey frizzy hair, and was probably not a day younger than 50. We went inside and ordered a meal, but all he did was talk about his work in insurance at the bank and about his orthodontist.

When he went outside to make a call, I went to the bar to get a drink and say hello to my friend. She commented, in all seriousness, "I didn’t know your uncle was coming to visit!" I nearly spat out my drink and spent the next few minutes in hysterics trying to explain that he was actually my date! Not my proudest moment but hey, it still gives me a laugh.

Disastrous Dates Facts Pxfuel

17. A Bad Beginning

One time on a first date, a guy took me to go see a psychic. She proceeded to tell him that we wouldn't last as a couple and would end up splitting up. I thought it was funny, but I guess he believed her pretty firmly. On the 2-hour drive home, he cried and said he didn't see the point in dating if we weren't going to end up in a proper relationship.

I just wanted to get the heck out of there, but to make matters worse, when he pulled up outside my house, he locked me in his van and wouldn't let me out until I threatened to call the authorities.

Creepiest Place FactsShutterstock

18. Starting Things off With a Bang

I met a girl who said she was outdoorsy and hunted, fished, etc. She wanted to hang out and she was cute, so sure why not? So I drove out to her house and we talked to her parents for a bit. Then her dad showed me his guns. No big deal. She asked if she could take me to the gun range. I’ve been around guns my whole life, so I was comfortable. I had no idea what was coming.

We started shooting some paper targets, and everything started out well. Then at one point, she asked me to go down-range and staple some more targets up. This is when it happened. I started walking down range and then BANG!...She accidentally shot me in the butt cheek. So, off to the hospital for me. I called my parents, and that was the last I saw of her.

Anna of Russia factsShutterstock

19. Speed Dating

I once went on a 10-minute date with an acquaintance from a group I hung out with. Everything was fine until the waiter showed up. Our waiter was African American, and this was apparently a big deal to my date. The minute the waiter turned to leave, my date started giving me his hate-laced views on the African-American race.

I was so shocked I didn’t even know how to respond. He zipped his mouth when the waiter returned, but the look on the waiter's face was clear; he had heard. I was HORRIFIED, mortified, and totally flabbergasted. As the waiter started to ask for our order, I was digging in my purse. I threw a $20 bill on the table, told my date I did not agree with anything he was saying and was very uncomfortable, and bolted for the door.

He called me daily for two weeks after that, saying we could go out again because he understood that I had left because I "was shy and just got nervous."

Disastrous Dates FactsShutterstock

20. Wrong Turn

I was on a Tinder date over a year ago, and had agreed to meet this girl to go for ice cream. She said she would pick me up along the way. We met, introduced ourselves, got in her car—and within 30 seconds of meeting her, she reversed straight into my neighbor’s parked vehicle. Not knowing what to do, I let her get out and check for damage.

She got back in the car, said it was fine, and we drove off. I looked in the side mirror and saw a big dent in my neighbor’s car. She also had a big dent in her car. Needless to say, it was an awkward ice cream and we did not see each other again.

They Can Never Get Over factsPixabay

21. The Roaches Check in; They Don’t Check out

I took a girl on a date to a new local bar. The bar wasn’t full, which was great, and there was live music playing. It seemed like a cool place, so we sat and asked for beers. Five minutes in, I felt something on my back. I slapped it with my hand, thinking it was a mosquito or something, and looked at the ground.

It wasn’t a mosquito. It was a cockroach. Gross, but I didn’t want to look like a wuss, so I ignored it and kept chatting. Two minutes later, she yelled and found a cockroach going up her leg. She shook it off and also decided to keep drinking and chatting. Suddenly, there was a bit of a commotion and we looked around. I can never unsee what I saw.

There were cockroaches going up the walls and tables everywhere. It was like an invasion, like the first Men in Black movie. Everyone rushed outside and looked back through the door. The cockroaches were everywhere. Every hole, every possible space on the ground, was wriggling and teeming with cockroaches. Apparently, the bar next door had put down some roach poison and closed its doors, so all the roaches had fled to the bar where we were.

Bug Infestations factsFlickr, ric_k

22. Below the Belt

I agreed to go on a date with this awkward guy from my school, mostly because I felt sorry for him. He showed up to my place to pick me up and hugged me. After I released the hug, he asked, "Can I have another?" I gave him a weird look, but figured okay, whatever. He leaned in for a second hug—and immediately went for a butt grab. Nope.

Airport Goodbyes FactsGetty Images

23. The Business of Bragging

After my freshman year of college, I met a guy on OK Cupid and we went to get dinner at Friday's as our first date. He offered to give me a ride, but I said no. He was a couple of years older than me, well dressed, and started talking about how he'd started his own business after college and it was going well. It seemed like he was bragging a bit but hey, that's an accomplishment.

After we ordered, he said, "Let's play a game. We'll each take out our wallets and compare what's in them." It wasn't a joke, he literally started showing me his credit cards and bragging about the high limits, ending with "Clearly, you can't afford to pay for this dinner, but don't worry I can cover you." I was annoyed and protested, but he wouldn't take no for an answer.

As we left, he said he wanted to show me his car. Unfortunately it was before mine in the parking lot, so I had to walk by it. It was literally a white, windowless serial killer van. I was pretty glad I drove separately.

Worst Dates factsShutterstock

24. Car Pharmacy

I agreed to a date with a guy I met online. He came to get me and seemed a bit weird, but I try not to judge people by their appearance. I had planned an evening of tea and movies, but he said he’d rather go to this party that his friend was having. I am very polite and I was trying to be open-minded, so I said yes. I regretted this almost immediately.

As soon as I got into his car, I noticed a funky smell. Then as he was driving, he pulled out bag of pills while explaining to me that he made his own version of a popular street substance. I politely declined, but he told me that if I didn't want to try that, he had other things. I then saw the collection of substances in his car. But it didn't end there.

Because I felt too awkward not to, I went to the party then an after-party, feeling trapped and extremely anxious the entire time. He dropped me off home later—and asked if he could have any of my medication. I awkwardly said no, and then gave up on love.

Brightest Things Said By Dull Students factsShutterstock

25. Maybe They Were Moving?

There was a guy who had been asking me to hang out for a while, but I had always said no because I got a weird vibe from him. He didn’t give up though, so I finally said yes, more to shut him up than anything else. He wanted me to go hang out at his house with his roommates, so I went. He then took me into the basement...where there was a dirty mattress on the floor, and nothing else.

I ran. To this day I have no idea what it was about, but I ran and never told anyone about it.

Disastrous Dates FactsWikimedia Commons

26. Stars In Mom’s Eyes

In the ninth grade, I agreed to a date with a guy from school. His mom drove us to the movies, and we had a pretty good time. When we got back though, everything changed for the worse. His mom started crying and saying he was going to be a big football star and that I was a gold digger just trying to capitalize on his success.

He was only on the school's ninth grade team, but she clearly thought the NFL was a guarantee. They had a family meeting. When my sister arrived to pick me up, they wouldn't let me leave the room until my status as a non-gold digger was verified.

Life Ruining Secret FactsShutterstock

27. A Family Affair

I had been friends with this guy for a couple months, and one weekend at a party we kissed. He was a nice guy, but a terrible kisser. He asked me on a date to go to an art gallery, and I thought that sounded really cool, so I said yes. What he failed to mention was that his entire family would be there—parents, siblings, grandparents, etc.

It was painfully awkward, to say the least. He invited me to have dinner with them, but I made my excuses and left, and said I had plans that night as well. Later, he showed up, uninvited and alone, to the party I was at that night. Creeped me out.

Unromantic Moments factsShutterstock

28. A Meaty Faux-Pas

I had a decent first date at a restaurant. She was a vegan; I'm not. After dinner, we walked out the door together and I playfully made a wisecrack: "So, do you think less of me because I eat meat?" Her dead-serious response: "Yes, I do. Eating meat is wrong. But don't worry, I'll convert you." There was no second date.

River Phoenix FactsShutterstock

29. Too Soon?

I think it was about my fifth date with this guy, and on a previous date, I had apparently mentioned something about my flat not having a full-sized bathtub. For our fifth date, I had agreed to a pizza and movies night at his place. The night was going okay, and then he told me he had to quickly do something in the other end of his house.

About 20 minutes later, he came back and told me to follow him to the bathroom. When I saw inside, I panicked. He had drawn me a bath. Lit candles and the clashing scents of aroma oils filled my nostrils. I know that it was, in theory, a nice gesture, but I felt completely stress out. To me, it was a very full-on act so early in a relationship.

He left the room and I sat there awkwardly in this bath for about 15 minutes, dying of embarrassment and awkwardness the whole time.

Messed Up As a Kid FactsPxfuel

30. False Advertising

I met a guy online who seemed really nice. We exchanged a few emails and got along well enough, so we decided to meet up for a matinee. We exchanged photos so that we could recognize each other at the theater where we were meeting. I showed up expecting to see a heavy-set dude around my age because that's what his profile showed.

Instead, he was about 20 years older than me, and 100 lbs heavier than his picture. I am a fairly open-minded person when it comes to dating, and I know that many folks embellish, but c'mon! We watched our movie in silence, and politely parted ways.

Disastrous Dates FactsShutterstock

31. Very Public Displays of Affection

A girl once took me to a Kumdo lesson, which is a Korean sword fighting sport, for a first date. I thought that was cool. It was an advanced class and I made somewhat of a fool of myself, but it was all in good fun. At least, I thought it was. It turned out that she had brought me there because she wanted me to be part of a documentary about foreigners in Korea.

Which meant that me looking like a fool was going to be broadcast nationwide. We then visited the grandmaster's house for makeolli and the film crew started interviewing me. They were basically focusing on my relationship with the girl I was going out with. They didn't seem to understand it was a first date. So I spent the rest of the date trying to answer awkward questions without embarrassing both of us on national television.

Attention-Seekers factsShutterstock

32. Meet the Parents

First time going out with a girl, she picked me up—and took me straight to her house to meet her parents. After a quick scripture reading, (I am not religious at all and still feel lucky not to have burst into flames while reading), her Father pulled out a banjo, which is my least favorite instrument next to bagpipes.

He then played several songs, including the complete instrumental from Deliverance. He was a very good player, but I was only thinking about playing with his daughter. Unfortunately, the end of the music was pretty much the end of the date.

Famous Real-Life Ghosts factsPublic Domain Pictures

33. You Had Me at “Wallpaper Shopping”

A guy who I liked moved pretty far away. We kept in touch with each other though, spoke a lot, and eventually he decided to visit me for a weekend. I imagined romantic things happening…but instead, he wanted to go wallpaper shopping. And so it was that our first "date" was in the home furnishings department of John Lewis.

He got lots of very ugly samples. Then we went to Habitat, where he looked at lamps and said the word "rimming" very loudly.

Disastrous Dates FactsPexels

34. Wrong Place, Wrong Time

I once went on a date with a guy who told me, while we were being seated at a restaurant, that there is nothing more disgusting than seeing a woman put food into her mouth. He said this with a facial expression of sincere disgust, and went on to explain that his mother was terribly obese and embarrassing to him.

Thankfully, it was a first (and last) date. So I came up with an ingenious plan. I did what any self-respecting girl would do and ordered the most expensive seafood on the menu and didn't touch it. It was a rather boring hour hearing him talk about himself, never showing any interest in my life. The irate look on his face when the bill came was worth it, though.

Worst Dates factsShutterstock

35. Playing Games

In college, I had been avoiding a date with this guy I had met at a bar and drunkenly given my number to. One day, he called me to ask what I was doing, and I told him I was walking home from the library. He said, "Oh great, because I'm outside your apartment. I want to take you to dinner." Sure enough, he was there.

Dumbfounded, I stupidly got in the car. I was wearing jeans and T-shirt and noticed with concern that he was wearing a suit. Not a nice shirt and pants, a full-on suit. So I immediately said I was going to go upstairs to change, but he insisted that it would be fine. We drove for a while, and he wouldn't tell me where we were going.

Eventually, we pulled into the mall parking lot. At that point, I was assuming there was a gas station or something nearby that we were stopping at. I assumed wrong. He parked and motioned for me to get out. We walked in, him in his suit, me in my jeans, to the mall food court. We got pizza and played games in the arcade. I didn't see him again.

Not Paid Enough FactsShutterstock

36. Madness Takes Its Toll

A cute guy from another school asked me out to the movies, and I was desperately grateful because I had never been on a date before. I spent the whole week being giddy. Then, the night came, and he knocked and I opened the door expecting to see my prince charming! He was there…but he was wearing lingerie, high heels, a bra, and full makeup.

He had neglected to tell me that he was taking me to The Rocky Horror Picture Show.

J. Edgar Hoover FactsShutterstock

37. Ateeeeeeeen-tion!

In high school, I had a crush on this guy who was involved in a lot of "extra curricular activities," but I didn't know him well enough to actually know what they were. After a couple months of talking, he asked me out, and I agreed. When I asked where we were going, he said he wanted to keep it a surprise. No problem, I thought, this is going to be fun. I love surprises! I was so, so wrong.

He picked me up and we drove for about 30-45 minutes, until we reached a big metal gate, complete with barbed wire and watchtowers. The gate guy took my date’s ID, welcomed him, and waved us in. It turns out that he was a part of an army program that trains you while you're in high school. He had taken me there to recruit me.

I sat there for 3 hours while they marched and went through protocol and tried to simultaneously get me to join in and talk to me about the benefits. They sent me home with a recruitment form.

Psychopaths FactsMarine Forces Reserve

38. Father Knows Best

My Dad does not usually involve himself in my dating life, but when I told him I was going out with one particular guy, he told me that he didn't like him, and that I shouldn't go. I thought that was strange, because he's usually pretty indifferent. Later, the guy came and knocked on my door. I opened it, and the first words that come out of his mouth were, "Oh, I thought you were going to wear something cute tonight." I guess dad was right.

Strangest Date FactsShutterstock

39. Spectacular Spectacle

About 8 years ago, I was working as a reporter for a regional newspaper. Just before Christmas, I had to go and report on a carol service happening at the local conference centre. I expected a carol service of the type I'd grown up with—a small community affair, "Hark the Herald Angel Sings" with some light moral preaching afterwards.

Instead, it was a full on, arm-waving, evangelical-sermon-spectacular, complete with a band and modern carols I'd never heard of, in front of about 3,000 people. I went home at about 9pm, not overly bothered because, hey, it was my job to be there. 10 minutes after, my housemate came in from what I knew had been a first date with a girl he liked from work. He looked shell-shocked.

Turns out the girl had taken him to the exact same event that I'd been at, and that she’d been arm waving and praising enthusiastically with everyone else. He's not religious in the slightest. I don't believe they went out again.

Disastrous Dates Facts Wikimedia Commons

40. Irony, You Suck

I had a date with this gorgeous girl, and within the first 30 seconds, it got bad. She opened with, "I'm sure glad you're not one of those guys with a fancy red sports car!" Before I could respond, we walked around the corner from her apartment to my fancy red sports car. The date only went downhill from there.

Dumbest Arguments Lost FactsPxHere

41. Crossed Cultures

When I sat down with my blind date to have dinner, she told me that she was a huge fan of Asian culture. My family is Korean, although I was born and raised in Canada. I groaned inwardly but nodded as I ate my pasta. She then went on and on about this love of Asian culture, and then produced a backpack that had Hello Kitty on it.

She opened it up and started producing tons of Hello Kitty merchandise. Pencils, makeup, pencil case, just stupid random stuff. She then showed me her Hello Kitty tattoo, and told me that she was even wearing Hello Kitty underwear. Then, I was torn. Part of me wanted to see if she would show me this underwear, but the annoyed part of me just wanted her to shut up.

Believe it or not, the annoyed part won. I told her I was Korean, and that Hello Kitty was a Japanese thing. I added that I basically just considered myself Canadian, and I had very little interest in something that would be considered "Korean" and less interest still in something Japanese. Her next response stunned me. She only said, "There’s a difference?"

Cats factsFlickr

42. False Accu-steak-tion

I met a young woman in the meat department of a grocery store. She looked in my cart and asked what I was going to cook. I told her some filet mignon, a salad, and baked potato were on the menu. She made a few comments about being jealous of my girlfriend, I told her I was single, we exchanged numbers, and had a date two weeks later.

She wanted to go to Outback Steakhouse. When I ordered steak, she called me a murderer. I told her I didn’t see it that way, she left, and then I ate two steaks, alone.

Floyd Mayweather Jr. factsPixabay

43. Red Flags

I met a gorgeous guy during my senior year in high school. He was 19, and I knew nothing about him, but I agreed to go out on a date anyway. He picked me up and took me to his Church—and we watched a documentary on Joseph Smith. At this point, I called my friend and had her pick me up because I was so freaked out.

Creepy Camping Experiences FactsShutterstock

44. Give up Trying to Make Me Give up

I was on a third date with a gorgeously giant linebacker. He was smooth, and seemed to have good intentions. We finally got to his place and, instead of initiating anything, he ended up explaining the entire Naruto: Shippuden plot. Meanwhile, I was sitting on his bed waiting for him to stop talking...but he talked about Naruto for well over 30 minutes.

Obvious Romantic Hints factsShutterstock

45. Mudding

When I was in high school, I went on a date with my brother-in-law's cousin. He was a good-looking guy and was nice when I met him, so I figured it would be a good time. I got all dressed up in a skirt, cute top, and heels. I even curled my hair. When he picked me up I asked him where we were going, but he said it was a surprise.

We drove out into the country and into a field. Right about that time, I was getting a little nervous. It turns out he was taking me "mudding." I learned that mudding is when a bunch of country kids get in their trucks, find a muddy spot in a field, and drive through it over and over. So I ended up standing in a field, all dolled up and in heels, to watch a bunch of boys play in the mud. No second date occurred.

Green Day factsPixabay

46. Handbag Hater

A guy I met in college asked me to go for dinner that night. I didn't know him very well at all, but I figured I might as well go for it, just to see what he was like. He picked me up and said that we were going to go to one of the most expensive restaurants in the city. When I started to object, he just said, "Babe you're worth it." Then he said we were going to make a stop first.

He took me to the mall and made a beeline for this really fancy leather goods store. He smiled, and told me to pick out any purse I wanted. I objected and said I didn't need or want a new purse. That's when he showed his dark side. He looked at me and sneered, "Your purse is falling apart. I don't want to take you to the restaurant with a ratty old purse like that."

I just stared at him and then turned and walked away and got one of my friends to pick me up.

Disastrous Dates Facts Peakpx

47. Tall Tales

I went on a date with a guy about a year after my fiancé had died in a car accident. I was up front with him about the fact that I had gone through a loss the year previous, but was excited to start dating again. I think he took this as a sign that I needed to be reassured. He confided in me that his first girlfriend had died of cancer. I felt comfortable telling him about my fiancé after that.

Well, then, a dealer had shot his best friend in front of him. And his last girlfriend had beaten him with a rope. And his other best friend had died in Iraq. And his sister had a terminal illness. And he had night terrors. And PTSD. And about 15 other things which, by themselves, would have been sad and unfortunate, but all piled up, started to seem fishy.

On the plus side, he had also won an engineering contest and had met the Queen. That was pretty incredible, as he had no college education or degree and worked morning stock at Target. Every day he would tell me more and more outrageous stories about his life, until I started asking questions about them. Then, I never heard from him again.

Worst Airplane Experience FactsShutterstock

48. Sub-Par

I went on a date with a guy who I met online. He told me to dress nice and that he was going to take me out for dinner. He took me to Subway, ordered a single foot-long teriyaki chicken sub. He looked at me and said, "I hope you like teriyaki chicken." We didn’t even sit at a table; we shared the sub in his car. Safe to say there was no second date.

Customer Isn’t Always Right factsShutterstock

49. Forget My Number

So I've known this guy for almost a year now, not really good friends or anything, more casual acquaintances. A couple of months ago he started messaging me, first on Facebook, then by text. He got my number from a friend, he didn't ask me for it. Most of the time I responded just to be polite. He's nice enough, but not really my type...

So when he started dropping hints about "meeting up," I just turned him down and said I'm busy, or we'd just catch up the next time there's a gathering with our friends, that sort of thing. Fast-forward to last week and he asked me out again, which is the 6th time in the past two months. I finally decided to at least give him a chance.

Hey, what could go wrong anyway, and who knows what I'm missing and all that jazz. Worst-case scenario it would be awkward, but we've talked more than a few times so I was thinking it can't be that bad and we could actually have a pleasant time. Date night comes and we meet up in the city after work. We have dinner; nice, cutesy Japanese place, conversation was okay.

I was certain at this point that it's really not going to take off, he really isn't my type, but I was having a pleasant enough time and he was a total gentleman and not bad to talk to. The bill comes, and I was going to suggest a quick coffee before heading home. However, he said that there's something he'd made an appointment for us for and we need to rush off to make it in time.

I was a bit intrigued and excited; was it a movie, or a show, a play (he knows I'm into theater)? So we hurry off and he took me to a high-end luxury mall with an attached wing for offices. I'm sort of still excited, sort of confused at this point. We went up...wait, this is an office lobby...what the...IT WAS A WEIGHT-LOSS CENTER.

So he explains that he's part of this company and he wanted to introduce me to their products that would "revolutionize" my lifestyle and make me healthier than I've ever been in my entire life. I was totally stunned at this point, so I was just nodding like an idiot the whole time we were walking inside. He then left me with his smarmy "teammates," who proceeded to give me an orientation about their company and a run-through of their health supplements.

I just sat through it because I knew that if I started to say something, I was definitely going to burst and make a spectacle of myself. After I flat-out said that I'm not interested in any of the products and frankly don't believe that I need health supplements (I eat well and exercise regularly), they started on the 2nd phase: introducing me to the "business" aspect of it.

Basically, it was a networking model of business where you not only sell the products, you also recruit people to sell them and they would be under your "team," and you get a commission for every sale they make. They rhapsodized about the wonders of the product, how easy it is to sell, and how much money I could be making, because they could tell I have the right kind of personality and network for it.

Registration was "only" $1,000, and it was consumable in products...which I could either use or sell to get my registration money back immediately.I wish I could say I flipped the table and screamed at them to screw themselves with their health supplements, but no...right after the "talk " I just said I should head home since it was  getting a bit late.

The guy actually messaged me to say that he had a good time and he hopes to see me again...and that I would reconsider their products and the "business opportunity."

Unromantic Moments factsShutterstock

50. A Trip Down Memory Lane

I met a girl at a church retreat. We decided to go out to a nightclub for drinks, but first we met up at her place to chat for a bit. To my surprise, she broke out a photo album. Its contents made my blood run cold. It contained a bunch of pictures of her with random guys. There was narration to match: "So, I cheated on my boyfriend with him, but this guy didn't hear about that…or about this guy, or about this guy. Oh, this one is actually his best friend. They don't talk anymore, my boyfriend doesn't know why." You can't make this stuff up.

Heartbreaking Relationship Issues factsPixabay

51. Girl Support

A guy in my college economy class asked me out for lunch. He said his car was in the shop, so I picked him up. On the way, he asked if we could stop at a place so he could take care of something "real quick." We arrived at the specified destination. When we pulled up, my jaw hit the floor. It was an abortion clinic, where his six-weeks-previous one-night-stand was waiting to be treated.

"It's OK if you want to come in," he assured me. "She could probably use some girl support, if you know what I mean." He didn't even have the car door all the way shut before I was escaping. For the rest of that semester in class, he flipped me off every chance he got. THAT part makes me laugh every time I think of it.

Awful First Dates FactsShutterstock

Sources: Reddit,



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