I’m Cringing: These Are The Most Awkward Restaurant Dates Ever
The lunch date and the dinner date are both essential activities for potential couples looking to get to know one another. But for every date that goes well and actually leads to a beautiful relationship, there are a whole bunch of other ones that have the completely opposite result! From terrible social skills to unexpected turns of events, restaurant workers bear witness to plenty of ridiculous examples of dates gone terribly wrong. Here are 50 stories of the most awkward restaurant dates people have ever witnessed.
1. Handing It Off
I’m a waiter at a restaurant where a lot of people come for dinner dates, so I think it’s safe to say that I’ve seen some pretty awkward things. For example, I once saw a guy shake his date’s hand when she reached over to try and grab some bread. It was probably the most awkward dating moment I’ve ever seen.
2. Silence Of The Clams
This is a date that I actually witnessed. The guy pulled out a chair for the girl. The girl didn’t realize what he was doing. Cue awkward pause. The couple then sat down. The guy cleared his throat and started coughing. The girl sat there, not knowing what to do. She proceeded to ignore him, then sheepishly picked up the menu and started reading it.
The waiter then came to their table. The girl asked her date if he knew what options were good. The guy said he’d have whatever she was having. He handed his menu back to the waiter, while the girl ordered seafood. Cue another awkward pause. It turned out that the guy was allergic to seafood. The guy took the menu back and looked for another minute. The waiter said he could come back, but the guy replied, “Don’t bother, I’ll just have a steak.”
The waiter left their table, leaving the couple sitting there, just blankly staring at each other. They weren’t even looking at their phones or whatever; they were literally just staring at each other in total silence until their food arrived…which they then ate in silence. My girlfriend and I were on the edge of our seats the whole time while watching this. We were waiting for something to happen.
3. From Bad To Worse
I used to bartend and waitress at a pub back in the day. One evening, a guy came in and sat down at a table for two. I asked him if he wanted a drink. He ordered a drink, then told me that he was waiting for a girl but would like to order food for when she arrived. He waited for a bit while I served him a couple of drinks.
An hour passed. He kept looking at his phone occasionally and drinking. At some point, he finally came up to the bar and told me he thinks he’d been stood up. He ordered a couple more drinks and pounded them back. He was starting to look and sound considerably worse. Still, he ordered a couple more drinks and I told him to wait a bit.
He convinced me to get the drinks for him anyway…by telling me he was just going to drink them and leave. And that’s what he did…except, just as he was about to exit, the most unexpected thing happened. Who should walk in at that very moment but his date? She was still wearing scrubs, looking pretty disheveled. She was clearly coming from some kind of medical work.
She apologized for being late. I then got to serve one of the most awkward dates ever. He was completely intoxicated from all the drinks he’d had while waiting. I honestly probably shouldn’t have given him that last drink or two. They made some small talk and it was terribly awkward. At one point, he got up and went to the bathroom.
Twenty minutes went by and he didn’t come back. Finally, one of the male servers walked up and told her that her date was having some troubles in the bathroom. Apparently, he was sitting on the toilet and bawling his eyes out. We asked her to get him out of there. We called him a cab and she pretty much shoved him into it before running the heck away.
4. Doing Everything Wrong
Tinder date. A guy kept ordering food for the girl, which was weird enough, to begin with—when you are legitimately having dinner with a stranger, why the heck would you think that’s okay? Anyway, he ordered her a drink that she didn’t want, so she corrected the order to a glass of something she did want.
Then, he ordered her some soup, which she also stated that she didn’t want. HE ordered her shrimp scampi for her meal—again, she didn’t want it, especially because she was allergic to shellfish. She was very sweet and I’m assuming she was trying to give him the benefit of the doubt.
That is until the conversation took a turn and she poured her drink on his head before storming out. Sadly, I couldn’t hear what he had said. There was one good thing about him, though. He tipped the heck out of me—he dropped almost a 60% tip on an already expensive meal. I would do anything to find out what he said to make this seemingly sweet girl pour cabernet all over him.
5. Parental Controls
I’m a waiter at a fancy restaurant. I once had a teenage couple come in for a romantic date, accompanied by one of their parents as a chaperone. Let’s just say that having a parent sitting with them and commenting on everything they tried to speak about did not exactly make for a very romantic evening. It was so awkward to watch!
6. Series Of Unfortunate Events
This one is sad. I was managing a restaurant at the time and I had a lady in her mid-forties come in dressed pretty nicely. She was not an ugly woman by any means, but she wasn’t overly attractive either. She was super excited to be going on a blind date and she even showed up early for it. She sat down and had a drink while chatting up the bartenders, servers, and myself.
We all really liked this woman. She was super sweet, friendly, and seemed to be having a nice time. But then her date showed up, and everything unraveled. He came in about a half-hour late and was talking on the phone. He sat next to the woman and continued talking on the phone. Finally, he got off the phone and went over to the bar to get a drink.
That was strange since the server would have offered to get one for him anyway. He proceeded to order a drink from the bar, down it, order another, and then just stay there, sitting. The woman tried to have a conversation with him, but he was constantly looking around the room as if he was trying to see if there was anything better that he could be doing.
Finally, when the waitress took their order, he asked for his food to go. When his food came out, he grabbed it, then got up and left. He tried to say something to me about how the woman was not attractive and he had to get out of there. He did it in a way where he tried to get me to agree with him. I just eye-rolled at him while he walked away.
The woman started crying and my entire female staff went over to the table to try and talk to her. I was going to basically let her hang out there all night and get whatever she wanted on the house, but she was too upset and left shortly after. That guy was such a jerk. She was such a sweetheart. It really angered me to see how he treated her.
7. Two Can Play At That Game
I once was a server at a very upscale French restaurant in New York City. One evening, a middle-aged man and a younger woman were seated in my section, clearly on a date. You could tell that this woman was his mistress by the way they interacted with each other. They were high maintenance, but pleasant enough nonetheless.
Right after they had received their entrees, the man looked across the way to another table and lost all the color in his face. His date noticed, and she turned to see what he was looking at. Her jaw dropped to the floor. The man’s wife was at another table, also on a date with her side piece, on the other side of the restaurant. The wife saw him and had the same expression on her face, which very quickly turned into rage.
She briskly walked over to his table and started whisper-yelling at him, as well as pointing her finger right in his face. He started to do the same back at her. It wasn’t a very big restaurant, so everyone could see what was going on and the atmosphere got icy real fast. The man’s date was just staring down at her plate, absolutely mortified.
She basically pretended nothing was happening and continued eating. Eventually, the wife stormed back over to her table and wolfed down her dinner. No exaggeration, she was like rage eating. He sat down and his mistress wouldn’t speak to him for the rest of the meal. This was a fine dining restaurant and they ordered multiple courses. Having to clear, crumb, and reset their table two more times was less than fun.
He left a very big tip though and apologized on the way out.
8. It Takes Three To Tango
We had a middle-aged lady come in with a gentleman. They asked for three menus. I went over to the table to introduce myself and asked if they were waiting for one more. The woman said no. She stated that her husband was with them. I wasn’t sure what she meant by that. Those at the table then ordered drinks.
When I came back to drop off their glasses, she said her “date” was in the bathroom. The lady explained to me that her husband had passed a few years ago and that this guy, a friend of hers, kept asking to go out. So she reluctantly said yes but insisted that her deceased husband come with them. This is why they had three menus at the table.
She instructed me to bring her husband up as often as possible and to act as if I knew him. She also told me to make sure I asked if he was having anything for dinner when I took their dinner order. She would refer to him just as if he was sitting right there. I then heard her tell the guy that he tried too hard and that he was kind of mean.
I do not miss working in the restaurant industry.
9. Taking The Question A Bit Too Literally
It was clearly a blind date. Neither participant was comfortable at all. I dropped off their drinks and both of them were polite. Then I dropped off their food and asked how everything was. The guy rolled his eyes and said, “Well, the food is great, but I just wish she would talk more!” The girl’s face went tomato red and I dropped off the check shortly after. Poor girl!
10. Playing Ketchup
To preface, I work in a restaurant where we make our own ketchup and some people just don’t like it. Fine, whatever—if you’re nice, I’ll bring you the secret Heinz ketchup as long as you don’t tell anyone. Anyway, a woman was seated at my table looking super excited. She told me she was on a blind date. She ordered a drink and waited anxiously. How cute, right? Wrong.
The dude showed up on his phone, completely ignoring the hostess. He eventually made his way to the beautiful woman waiting for him. He continued to talk on his phone for like fifteen minutes. When he finally hung up, I went over to the table. He tried to order for her, which obviously embarrassed her. For himself, he ordered a well-done steak and fries.
When I brought it to him, he asked for a very specific brand of ketchup. When I informed him that we didn’t have it, he grunted and said he had some ketchup packets in his truck. As soon as he walked out the door, she asked for her half of the check and her food to go. I helped her leave out the side door before he could even come back. It was awkward serving him after that.
He used seven ketchup packets.
11. Starting Off Strong
I once witnessed an awkward date, during which the couple broke up. The thing is that he dumped her near the beginning of the evening, so they had to sit there for the next hour or so and live with the aftermath. The girl literally cried while giving the waiter her order. I’m surprised they managed to finish their whole meal, including dessert and all.
12. Popping The Question
It was my first day as a server at a sushi restaurant. I was 17 years old at the time with minimal people skills. I had just checked in an older woman, possibly in her early 60s or late 50s, with a young man who couldn’t have been older than 25. Midway through their meal, I went to check up on them, asking, “Awww, are you taking mom out today?”
They both turned to me with straight faces and the young man answered, “She’s my girlfriend.” I whispered an apology and just peeled myself away…
13. Foot Traffic
The most awkward date I’ve ever witnessed was probably the one where the guy’s choice of footwear was such a turn off that the woman didn’t even sit down with him. She left before he even saw that she had come in. I was a hostess at the time, so I had to go and awkwardly explain to the gentleman that his date had arrived and left.
When he asked if she gave a reason, I had to tell him that she didn’t like his shoes. His choice of footwear? Those strange running shoes that look like feet. The ones where each individual toe goes into a separate slot like toe socks. Luckily, they were black and gray and not any sort of crazy colors. He wore them with a nice grey suit. It was… really bad looking.
The man was devastated. Also, this was more than seven years ago…long before these kinds of shoes were even “popular.”
14. Paying It Backward
Not a date per se, but the end result was the guy paying for the girl’s meal and drinks. A very chatty woman in her early 20s was at the bar ordering more than a few drinks; probably five or six cocktails and a few beers. Did I mention that this was the middle of the day? Anyway, some guy sat next to her and they ended up chatting. Good for them.
Eventually, it was time for her to leave and she handed me a credit card. I put the card in the machine and it got declined. She apologized and fished around for another credit card. That one declined as well. She then got a little pouty and played the “woe is me” card. The White Knight next to her swooped in and told her not to worry; he’d pay the bill, which was around $100.
I guess he was expecting to get some and take her home. But as soon as he paid and the card went through, she fast-walked out of the place and was never seen again.
15. Waiting On A Friend
I waited tables during college. The most awkward date I ever saw involved a lady in her mid-30s who got stood up. Like, an hour in, she was still waiting and drinking her third glass of chardonnay. It was really sad to see her come to the realization that her date had stood her up. But by that time, she had more than three drinks in her.
She ordered food and just talked to random wait staff from time to time. I’m fairly certain that she ended up convincing one of the waiters who was getting off his shift to go home with her.
16. Off The Walls
I walked into work at 5 pm one evening, The only people in the bar was a couple on a date. A fellow bartender walked out of the restroom, shaking his head in disbelief and shock. He immediately started pointing at the guy and told me what happened. When I walked into the men’s room, the sight was so gruesome I almost threw up. it looked like a bomb exploded in there.
A waitress asked me if she could say something to the gentleman. I was so angry that I said sure. She walked up to the table and asked the guy if he had pooped himself or if he needed a doctor. The woman on the date then turned around in complete confusion and asked the waitress what she meant.
The waitress then replied: “He knows what I’m talking about…he pooped all over the wall in the men’s restroom!” The woman on the date shoved her plate and drink into the guy’s lap and said: “Really, Vince? Again?!” He ran out of the restaurant as fast as he possibly could before we could make him clean it up. Hard to think of how a date could get any more awkward than that…
17. Child’s Play
My girlfriend and I went to a hibachi restaurant one time and we witnessed the most cringeworthy moment you can possibly imagine. We sat down at our table and were joined by another couple. We said hello to each other and casually talked with the strangers. Just before the chef began to cook, the woman handed her boyfriend a small gift bag.
The guy opened the bag and found a card in it with an ultrasound picture inside. The man was visibly upset and embarrassed. He kept telling her that she knew he didn’t want any kids. A hushed argument ensued after that, and at one point, the woman disappeared into the bathroom. He then told us that he didn’t even like the woman and he especially did not want a kid with her.
We then finished our meals in awkward silence. We often wonder what happened to those people.
18. Not As Advertised
One time, my boyfriend and I went out to dinner. Sitting directly in front of us was a middle-aged man wearing basketball shorts, a t-shirt, and flip flops with socks. He had ordered himself a large appetizer and was drinking a beer. Five minutes later, this younger, attractive, and very nicely-dressed woman came in and sat with him.
You could tell by the look on her face that this was the first date and that he was not what she had expected. By this time, he had already eaten most of the appetizer. He started talking very loudly about how tiny her body was and how he was a big man who liked to be in charge. We felt terrible for this girl! She was very mousy and seemed too sweet to say anything.
He kept trying to get her to take shots with him while urging her to crash at his place afterward. When my boyfriend and I were leaving, we made the bartender aware that the girl looked to be uncomfortable.
19. The Middle Man
I work in a Chinese restaurant. One day, a couple in their 50s came in and the husband asked if anyone spoke Mandarin. I brought out the owner. It turned out, the couple had just gotten married in an arranged ceremony. The wife had just arrived from China, so she didn’t speak any English, and the husband didn’t speak any Mandarin.
The owner ended up sitting with them for the entire hour-long dinner date, translating everything they wanted to say to each other…
20. Feeling It In Your Heart
One time, I was at a restaurant watching an older gentleman on a blind date get knocked out of his chair due to a heart attack. He had a built-in defibrillator and I guess that’s what caused him to get knocked out of his seat. The girl he was with was in complete shock and did not know how to react to what she was seeing.
21. Rock And Roll
I once saw something super awkward while waiting for a take-out order at a sushi place. Around 3 pm, a guy came in and explained to the staff that he was coming in later that night with a date. He wanted them to come out with a roll and say: “Hi so and so, nice to see you again, this is on the house.” He thought this would impress the girl and make him seem important.
The waitress gave him the blankest look, so he explained the whole thing again, emphasizing how he would actually pay for the roll. I should have gone back later to see how that played out.
22. Change Is Gonna Come
I once saw a couple in their mid-twenties on what appeared to be their first date. The girl was clearly way out of the guy’s league and the guy was apparently completely broke. I mean like trying-to-make-it-work-on-literal-pocket-change broke. Every time she tried to order something, he was like, “No, do you guys have anything cheaper?”
At one point, he had a pile of change out on the table and they were counting it out together. What a cute date activity! They ended up getting just water and an order of french fries that they shared. She looked horrified, but to her credit, she stuck it out for the duration. I felt bad for the guy, but at the same time, I just had no idea what he was thinking.
And no, for the record, it was not Dave Chapelle.
23. I Propose You Change This Plan
A guy waited at a table-for-two for his “fiance” to show up, only to get on his knees and propose pretty much the moment she sat down. From the look on her face, I knew that things were going to go downhill real quick. I was working at Olive Garden at the time, and they ordered some pasta. Everyone could hear them arguing the entire time.
But mostly, you could hear the woman repeatedly saying, “YOU KNOW HOW I FREAKING FEEL ABOUT HIM!” The fight continued until I heard a loud “OHHHHHH!!!” She then threw an entire plate of pasta at his face. She stormed outside, he followed, and eventually, an officer came and took the woman in. I assume the charge was aggravated assault or something along those lines.
24. Bathroom Break
I once served a table where the girl showed up first and then the man. She was super quiet and so was he, until like thirty minutes in when he started screaming at her and she went to the bathroom. The table next to them was shocked. That’s when he said something so horrific, the whole room went silent. “What are you people looking at? Do you think I’m gonna beat her? I’m not gonna freaking beat her!”
They had said nothing to him at all. The couple obviously broke up during the meal, and I told two off-duty bouncers what was happening. They found the girl leaving the bathroom and they said they’d walk her home. We also told her not to worry about the tab for the meal. She left with the bouncers and the guy said nothing about the event.
Nothing. He just asked for their check and left. When he was gone, the girls next to their table spoke up about it to me. They were young college girls, so I had to explain to them that if they ever saw this going on or if it was happening to them, they needed to let their server know or another server discreetly so that we could make sure they get a ride or walk home.
They were totally shocked that the restaurant staff would do that for them. I hope they told their friends they could use that, too.
25. Picking A Side
I am a friend of a server who told me that the worst date she witnessed happened on New Year’s Eve with a 50-year-old man and a woman in her early 20s. All of the booths were filled, so they were seated at a table for two. But the woman sat in the guy’s lap the whole time. In his lap! What the heck? Their plates were pushed side by side awkwardly and half of the table was not used.
And to top it all off, they dined and dashed. Cheap weirdos.
26. Wanted On The Telephone
I was once working a shift at an outdoor restaurant. It must have been their first date or something because the girl was endlessly texting while the guy was talking to her. He just kept talking and laughing, and she just kept saying “….Yeah,” or “Cool,” or “Nice.” She wouldn’t even look up from her phone once, and this went on for a straight thirty minutes.
I would have “gone to the bathroom” and never come back if I were him.
27. Mixing Work And Pleasure
This wasn’t so much a date, despite her trying pretty hard to make it one. I was eating at a pub near my work with my parents on Christmas Eve when we saw a work function nearby getting really rowdy. There was this woman, probably in her mid-forties but trying very hard to look like she was in her mid-twenties. Honestly, her attempt to look young aged herself even more.
She was hitting on her coworker pretty heavily. He seemed really uncomfortable about the whole thing and he frequently tried to get her out of his hair by moving seats around the table to talk to other coworkers. She kept following him. We were finishing up our food when he got up to leave, saying goodbye to everyone and telling them that his ride was there.
We watched her follow him out where he was meeting up with this handsome guy, whom he kissed. He introduced him to her to as his husband. He even pointed to the rings on their fingers. Looked pretty darn awkward for her!
28. A Christmas Carol
I once had a couple on a date who were regulars. They shared a bottle of wine and were having a great time. About 45 minutes into their meal, the table across from them was seated with a large party. On my way to check on the couple, one of the people in the large party pulled me aside and asked me what their coworker Paul was doing with that young lady.
I told them that he was on a date and that they’d been there a few times together. The gentleman looked at me in disbelief and said, “But I just had lunch with him and his wife, Carol, earlier this week!” He proceeded to point Paul out to the rest of the group, who were all familiar with Carol. Paul was not with Carol that night…
29. Baker’s Dozen
I’m not a server but I used to work as a bakery clerk. The bakery was attached to a restaurant. I had to go inside the restaurant and pass out samples, and I witnessed a table where the guy was on his phone the entire time. It didn’t seem too bad until they came to the bakery afterward and ordered cake slices. I asked them if they wanted their cake slices in the same box or in separate boxes.
The woman said the same box and her boyfriend interrupted, saying, “NO. SEPARATE BOXES.” It didn’t seem like a big deal, but this woman completely lost it. She started listing off everything he did wrong and how he was probably cheating on her with his ex. It was absolutely glorious to witness.
The list of things that this guy did wrong according to the girl included: not paying for her meal, not sharing his fries (I can see why she would be mad at him for this), ignoring her for the majority of the date, not complimenting her outfit or makeup, and using his vape in the restaurant. There was a lot more to the list, but it was hard to understand what the girl was saying towards the end because she just started crying uncontrollably.
30. Scenes From An Italian Restaurant
I worked at a nice Italian restaurant at my university. One day, a nice man came in to make a reservation and explained that he was going to propose, so he wanted a certain table to mirror things that had happened from their first date. It was really sweet. He seemed so in love and we were all quite excited for him!
When they came in, she was excited and impressed with the table. Things appeared to have been going well, at least from a distance. We finally get to the big moment. The ring was hidden in her champagne bottle. We bring it out and they just go hushed tones and quiet. It was a slow night, so we were all watching. That’s when things took a turn for the worse
The hostess had been asked to take pictures to send to the guy later. We couldn’t hear what they were saying, but the next thing we knew the guy gets up and won’t even look at her. He leaves the table and she just puts her head down and cries. She said no. She didn’t tell us why, but she seemed quite distraught. We all ended up consoling her, weirdly enough.
31. Two For The Price Of One
I used to be a DJ on a dinner harbor cruise. This 40-year-old dude had some decent cash and he upgraded his regular dinner date to include a special table and event coordinator. He also arranged for one of his buddies to be a videographer and booked some time for his own special dance with his girlfriend, which would open the dance floor for all the guests.
He arranged to have two dozen roses waiting on the table when they arrived, plus a treasure chest filled with 75 more for a total of 99 roses. The treasure chest would be brought out by the coordinator and another member of the serving staff at the end of the aforementioned dance. At that point, he would propose to the girl.
I was informed of this all ahead of time because, as the DJ, I needed to welcome them out to the dance floor for their special dance after dinner and make sure the rest of the guests did not interrupt. So the couple showed up and the girl looked like she was probably fifteen if not twenty years younger than the guy… but the evening went on as planned.
Things continued smoothly right up to the part where the song ended and he got down on one knee. He took her hand, held the ring at the tip of her finger, and asked her to marry him. She just stood there. The music stopped. The event coordinator and server were holding the roses. The friend was filming. She just stood there giving no response.
Now, there was a good 60 to 80 other people in this level of the boat, sitting in uncomfortable silence while watching this unfold. I can’t say for sure how long it went on for; could have been thirty seconds, could have been five minutes. Every so often, he would whisper to her, and eventually, she let him slide the ring onto her finger and they slunk away back to their table.
Now, here’s the icing on this tragic cake of awkwardness. I was talking to a server afterward and they told me that another guy at a different table ordered a “celebration” dessert for the happy couple. Well, dessert time rolled around a while after the incident, and the waiter brought out the dessert which said “Congratulations” on it.
The woman at the table looked confused and the man gave the quickest of head shakes. The waitress acted as if she confused tables and just walked away. The first guy’s proposal went so bad that it scared the second guy off from even trying. So he managed to blow two proposals in one night!
32. I Scream For Ice Cream
I work at an ice cream parlor. A couple of years ago, I had a couple come in. It seemed like their first date. They were kind of nervous around each other, but they seemed to get along well. They were looking over the menu at some point finally decided what they want. They were standing at the register, and the girl took out her wallet to get ready to order hers.
He insisted that he’d pay, which led to them spending a minute or two going back and forth over this. They finally came to an agreement that he would pay. Thank goodness. It’s always awkward standing there while people argue over who will pay, and even worse when they both shove their credit cards at you and expect you to choose who is responsible for the bill.
They ordered. I went to get their sundaes and rang them up. Once this guy saw the total, which was probably like $10 or less, he awkwardly stood there for a minute and said to me, “Can we do them separate?” He then turned to the girl and said, “You still wanted to pay for your own, right?” She replied, “What the heck?” and slowly got her wallet back out of her bag that she put away WHEN HE DECIDED HE WOULD PAY.
She was like, “Yeah sure, that’s fine…” They then sat inside in mostly silence. She clearly was no longer interested in him. I didn’t know who to feel bad for. I’m all for splitting the bill. Like I would never expect a dude to pay for me just because I’m a woman, but after the few minutes they spent debating and he insisted, and then instantly changing his mind because his date was not worth five dollars…well, that’s just awkward.
33. Blood Money
This just happened about an hour ago. There was a pre-prom dinner or something like that at my restaurant. They had taken pictures today so they wouldn’t have to do it tomorrow. The guys and girls were all done up in suits and sparkly dresses. One girl got up to use the bathroom, and I guess she didn’t know it was that time of the month.
Her dress had a huge red spot on the back of it, and she had absolutely no clue. A female server ran in after her to tell her, and they explained this to her date. Her date said, “Well there goes my night and weekend!” before immediately leaving the restaurant. He left her with the bill too.
34. A Family Affair
This wasn’t exactly a date, but still one of the most awkward situations I’ve seen. I used to bartend at a pretty fancy Cajun place in my hometown. One night, I was fixing some salads while my coworker was bartending. An older couple sat down at the bar and placed their orders. Nothing out of the ordinary at that point.
Ten or fifteen minutes passed and in walked one of my brother’s friends who I recognized. She sat down in between the couple who ended up being her parents. Anyway, they continued to act completely normal and were actually quite pleasant to serve. But then something horrible happened when I left to grab their appetizer from the kitchen.
When I came back, the gentleman was laying into his wife about this and that. I try really hard to tune out other people’s conversations while bartending since it’s none of my business but sometimes it’s hard to do so. The only words I really caught from the conversation were “ungrateful” and “you should be ashamed.”
Now, mind you, this couple only had two drinks at this point and they seemed completely sober when they walked in, so intoxication shouldn’t have played a part. I felt so sorry for their daughter. She looked mortified sitting in between them and she just kept sipping her drink while occasionally begging for them to stop fighting. The couple ended up leaving separately, and their daughter stayed behind looking so, so broken.
I felt terrible for her, as I come from a broken home. So I went over and introduced myself, saying how I recognized her from my brother’s friend group. I bought her a drink. Super nice girl. It’s a shame she had to endure that mess in public.
35. Room For One More
I worked at a semi-casual restaurant and we have a decent amount of blind dates. Once, I had a gentleman arrive for his reservation. I seated him at Table 8. Then, I had a lady show up “looking for her friend.” I asked her if it was the gentleman at Table 8. She thanked me and went over to sit down with him. Well, they started hitting it off great! They ordered drinks, apps; the whole thing.
THEN, another guy came in saying he is waiting for his friend. He was standing in the lobby, texting on his phone. Eventually, we caught on that he was also on a blind date, and was supposed to be with the girl at Table 8! The girl eventually came up after getting a text from him, apologized, then sat down with BOTH guys to enjoy all the apps.
Eventually, she suggested that her date was actually with the second guy, and that the first guy should just head out. It turned out that the first guy was stood up on his own blind date. It was such a mess, and the first guy was royally annoyed that he was being kicked out after buying them food.
36. Slowly Backing Away
When I worked at a drive-thru coffee shop, my team and I saw this super awkward teenage couple on their first date. We were right by a high school and movie theater, so it wasn’t anything unusual for us. However, as he got ready to back mom’s minivan out of a parking spot, the poor kid hit the gas pedal by mistake. The car went straight into the marsh behind our parking lot.
Ambulances, the fire department, and his mom show up a bit later. Everyone was fine; it just ended up being one case of severely wounded pride.
37. A Thankless Job
The date started out kind of okay; maybe a little awkward as first dates usually are, but they both ultimately decided at the end of the date that they weren’t a good match. The woman said she would pay for her own meal. The man declined and says he had every intention of paying since she humored him and gave him a chance. I was thinking to myself, “Aww, that is sweet, even if they didn’t work out.”
The woman thanked the man and left in an Uber as I was grabbing the check. Then, the man’s credit card declined. The man had to awkwardly call the woman up to ask her to pay the entire bill because he didn’t have any money. The woman came back about ten minutes later, but the man was hiding in the bathroom by that point so that he didn’t have to look her in the eye.
It was sad because the woman wasn’t even mad about it. She just seemed peeved that he would hide instead of thanking her. It was really awkward.
38. As Time Goes By
The most awkward date that I’ve ever witnessed in the restaurant where I work is “the date that never happened” as we like to call it. This poor, unfortunate dude sat in a booth of mine for more than hours waiting on his “date” to show up. Every few minutes, he kept letting me know that she was still coming, just running late. He refused to acknowledge that he had been stood up.
39. Time To Split
This guy had been coming in regularly to my restaurant for first dates. One day, he came in again. The customers order at the bar, so he came up and asked for two spaghetti platers. Fair enough. I brought ’em over and put them down. The girl said: “Oh, I actually wanted the vegetarian spaghetti!” After an awkward interaction, she proceeded to eat it anyway.
In the end, the bill came. I asked: “Together?” He said: “No, split.” I’ll never forget the look on her face.
40. Great Ex-pectations
While grabbing a bite to eat one time, I was within hearing range of an awkward date situation. It was actually at a staff cafeteria while I was working for Disney. This young woman had clearly been trying to set up these two young gay men for a while. Finally, their lunch hours collided. so she thought she could introduce them to each other and let them get to know each other over lunch.
She got them set up, told them what they had in common, and left. The disaster started from there. One of them kept talking about his ex-boyfriend while the other guy became more and more frustrated. I can’t decide if I feel worse for the guy who had to hear about someone’s ex for half an hour or for the poor girl who worked so hard to try and set them up.
41. Sometimes It’s Better To Say Nothing
I once overheard this while eating out at a restaurant. My family and I got seated and behind us was this couple on a date. The guy got up to use the bathroom. When he came back, he started talking about his own pee and comparing it to the waters of Niagara Falls. The woman he was with was Korean. When she told him that, he talked about how his buddy had a farm that employed fifty of her “people.” She was not impressed…
42. Party Of Fourteen
I didn’t just see this date; I was a part of it. I went to meet a guy wearing a t-shirt and jeans. It was going to be a casual date; nothing unusual. When he arrived, he was wearing a button-up shirt, a tie, and dress pants with fancy shoes. He kept acting suspiciously the entire time; like, constantly looking over his shoulder.
We’d go into one restaurant or diner and he’d say, “Not here,” so we’d walk to another. Finally, when we settled for a place, I saw him looking around nervously. He then just spilled it all. “My entire family has been following us for the last hour.” That was when I saw a group of twelve enter the diner, and he just said: “Uh oh, they are here.”
They sat behind him and kept staring at him, smiling. We were just eating our appetizers and stuff but it was super creepy. He kept apologizing, saying he’d make it up to me. That’s when I realized they were all wearing super fancy, button-up clothes; the type of stuff you see at a wedding, funeral, or some really crazy important event.
The cogs in my brain were tinkering at that point. If they followed us for the last hour, I wanted to mess with them as much as possible. After we finished our meal with his family just sitting behind him, I said “Well, let’s go.” My date was completely confused as I practically dragged him out of the diner.
The first place we stopped at was a drugstore. I bought things like candy, soda, and condoms. As we exited, I saw two SUVs with what I assume was his father sitting in the driver’s seat of one and his mother sitting in the driver’s seat of the other. The next place we went to was a motel nearby. As we parked, I noticed the two SUVs slow down in front of it and then slowly creep away.
I walked out grabbing his hand with our goods and I MADE SURE that they saw us. I walked in and got us a room. My date by this point was dumbfounded, giving me a “are we seriously going to do this?” look.
Boy, did we. Afterward, we were resting for a bit when there was a knock on the door. His parents were there to “collect what was theirs.”
I never saw him again. Not in school, not accidentally on the street, not anywhere. His Facebook disappeared too.
43. With A Little Help From His Friend
I’ll tell you one that I experienced first-hand. Back in my youth, I had a guy show up with a friend who I didn’t know would be joining us on our date. Then, when we get to the movie theater, neither of them brought their wallets. The guy in the ticket booth was slack-jawed and so embarrassed for me. At the end of the night, the friend actually started to openly dictate to my date what he should do next.
Him: “Okay, so now you walk her to her door and give her a kiss goodnight. Go for the lips.” Me: “Oh no, I’m good thanks.” He kissed me on the cheek anyway and ran off into the night screaming and giggling. A couple of days later, I had people coming up to me asking when I became that guy’s girlfriend. When I stated that we only went on a single (and quite a bad) date, he got wind of it.
He and the same friend rushed me in the hallway and he was holding back tears. He demanded: “You’re telling people you aren’t my girlfriend?!” I said: “It was one date and it didn’t go well, man…” That was definitely not the answer he was looking for. I felt pretty bad for him, but also, what the heck was he thinking??
44. Time Marches On
So, my last relationship ended quite poorly. I won’t go into details of that here, but it was sufficient enough to keep me from seriously thinking about dating for a couple of years. I was finally feeling up to it after some prompting from friends, though, so I took a gander at online dating. I was like, screw it, I can at least pretend to be charismatic and confident enough. Anything can happen, right?
Thus began my foray into online dating. Using an app that has something to do with coffee, I matched with a gal who will be referred to henceforth as W. To my great relief, W was not a bot, and she was actually quite responsive to my awkward and rusty attempts to talk to her and get to know her. Eventually, we decided to meet up using the old fashioned idea of a lunch date.
The place she suggested was a small but very chic Italian restaurant nearer to her home than mine, which was no problem for me because I drove. I made the reservation and, on the day of the date, I got there about five minutes late because of traffic. I texted W to let her know. She texted back, saying that she was still waiting for public transportation.
That was fine with me. I went ahead and told the staff of my reservation, who then proceeded to seat me by the window. I began waiting, taking a look at the menu first, and then ordering coffee. Guys. I waited for an hour and thirty minutes. If it wasn’t for W texting me updates every so often and apologizing profusely, I would have left at the thirty-minute mark.
I can only imagine how stupid I looked to the servers, who could determine two things accurately: A) I was looking out the window for ages and B) I was alone at a table and had a reservation for two. And from the frequency with which they came by to ask if I needed anything, they sure as heck had determined that I was some dumb unlucky sap being stood up.
W did arrive eventually though, extremely apologetic. I teased her a bit and the rest of the date went pretty okay for a first date. We went to a park afterward—I have to thank this random elderly gentleman and his dog who made me look good. W loved dogs, especially Shibas, and the gentleman’s Shiba much-preferred playing and interacting with me over her.
We’ll probably be planning another date next week.
45. From One Set Of Bars To Another
I’m a former bartender. One night some time ago, this couple was having a flirty date at a table close to my bar. They were two rounds in and having a great time; laughs, kisses, flirting, the whole thing. Then, a lady came in and sat at the bar. She seemed off. She stared at the bar menu for a good five to ten minutes. The menu was upside down this whole time.
I figured out that she was there watching the couple behind her through the bar mirror. I went over to greet her. As soon as I got close, I saw that she was wearing a wig. A bad one. She took her sunglasses down and I noticed that she had been crying. At that point, I was intrigued. She was not getting a drink until I got her story.
It turned out the couple behind her was her husband and his mistress.
For the next hour, I had to give her a play by play of her husband’s date. So awkward. She was devastated but kept wanting details. Then, she handed me forty dollars to buy them one round. What the heck? But it was a $22 tip for me, so okay. I sent the drinks to the table with my compliments. They waved thanks.
Later on, she asked me to send another round. I did it, knowing the couple would be intoxicated at this point. The couple finished up and left. They even stopped by the bar on the way out. He shook my hand and said thank you for all the free drinks…right next to his wife sitting there! They left. I then saw the wife’s plan unfold, and it was epic.
She pulled out her phone, called the authorities, and reported an intoxicated driver. She gave his car description and license plate number, saying he was on the road she knew he would take home. Brutal, but deserved. It would also be his fourth DUI charge, so that meant he would have to be spending some time behind bars.
46. High Heat
I was a bartender at a burger joint. A creepy sandal-wearing older gentleman who was a regular brought in what appeared to be a younger escort. Per our operating procedures, I asked her what temperature she wanted her burger cooked at. The man then interjected and said, “medium rare” while staring into her eyes and licking his lips. I will never forget how awkward that moment was…
47. Well, That Was Unexpected!
We had one guy who would come in with two different women separately. They were both around the same age. Maybe one was a sister, who knows?! But he was a regular and was always with one of them. We were a nicer restaurant, so we mostly had couples coming in…including that gross older man.
The rumor among the servers was that he was dating both of these women. Then, one time, the only time that I know of at least, he came in with both of them! We were all shocked! Maybe it wasn’t awkward for him, but it was for us. The ladies sat next to each other on one side of the booth.
The dude was pretty nice though. My parents ended up going there for an anniversary and sat in the booth next to them. He overheard that it was their anniversary and paid their bill.
48. Too Much Information
My first job was at a Hardee’s. This massively overweight woman came in carrying a Walmart bag. A guy followed after her. They were both well into their forties. I was cleaning the tables and happened to overhear them. The guy asked if she brought the “stuff.” She replied saying that she did. They then began to talk about, in full detail, about the unusual intimacy that they were about to have.
The guy said something along the lines of how she was “not going to be able to poop right for a week.” By this point, they were both sweating profusely. They both then quickly got up, getting ready to leave. Just as they exited, I noticed her bag sitting on the floor. I had a rag in my hand, so I picked up the bag with the rag, ran after them, and said, “Ma’am, you forgot this.” I couldn’t even look her in the eye.
She took it from my hand and said, “Thanks. I’m gonna need this later.”
49. Wild Goose Chase
I’m a waiter. We once had two couples share a table for a double date. It appeared to be the first time that any of them had gone out together. At the end of the dinner, they all tried to dine and dash. I chased them down, and the girls had no clue. Apparently, their dates had told them that they already paid. The girls ended up paying for everyone, as the guys had no cash.
50. Ain’t No Sunshine
We have a rich, middle-aged guy that comes in almost every Friday with a new date. A couple of servers I work with have a weekly pool on whether the date will last shorter or longer than thirty minutes. Unders have won probably about 70% of the time. I think the best story I heard from one of his dates was when he asked where the lady was from. She answered Miami, and he immediately told her to leave.