Servers Share The Most Cringe-Worthy First Dates They’ve Witnessed

September 15, 2023 | J. Hunter

Servers Share The Most Cringe-Worthy First Dates They’ve Witnessed

First dates aren’t just awkward for the two people on it, but for everyone around them. The awkward silences, random outbursts, and just all-around confusion do make the best stories. The secondhand cringe, horror, or pity can be felt by fellow patrons and servers. These true stories will prove just how uncomfortable first dates can be.

1. Mixing It Up

I worked at a bar where most of the business came from Tinder dates. Once, two guys came in and were at different tables along the same wall. Both were facing the door clearly waiting for dates. You can see where this is going. Eventually, a woman came in, walked up to the closest guy, and sat down. Then they started chatting and ordered their drinks.

Five minutes later, the other guy stood and went over to the couple. He said to the girl, “Hey, aren’t you…?” He told her his name and said, “We were supposed to be meeting I think". There was a lot of awkward laughter. Clearly flustered, she went to sit at the other table. A few minutes after, the other woman arrived.

He was lucky and had something to break the ice. He told her all about what happened, and they laughed together.


2. Behind Closed Doors

I was playing in a band at a club where there were about 30 people. A couple had been sitting close together in a corner booth but disappeared together into one of the bathrooms. In between songs when it got quiet, the bartender yelled out, “They better not be in there doing it on my sink!” Everyone stared at the door.

And as the whole club was focused on it, the couple emerged. They were smiling at first. But when they looked around and saw everyone staring at them, both their faces turned red with shame. They quickly paid their bill and left.

Waiter AwkwardPexels

3. Pool Cue To Leave

I was bartending one night when a friend of mine came for a first date. Her date ordered their drinks, and they went to play pool in another room. Soon, he was back and ordered another round but asked to make her drink a double. I immediately felt like something was off. I knew her well enough to know that she wouldn’t order a double.

So, I poured her a single. He took the drinks, and I followed him into the pool room to “wipe stuff down". I pulled her aside and asked if she’d ordered the double. She said no, and I told her, “Well, he did. Did you want me to end this date for you?” She nodded. I turned to her date and asked, “Why get her a double when she didn’t ask for one?”

He started stammering, but I just pointed to the door and sent him out.

Waiters awkwardUnsplash

4. Worth The Wait

I was a bartender at a place close to the university that was considered a “hidden gem". First dates happened all the time. Once, a guy came in, sat at a table, and then looked at his watch. I greeted him and asked if he wanted a drink. He looked concerned and asked, “Is it rude to get a drink before the other person gets here?”

I shook my head and asked if he was waiting for a date. He nodded, so I suggested a drink for him to sip on to calm his nerves. He agreed and apologized profusely for bothering me, which he wasn’t, and kept waiting. After 20 minutes of him looking at his watch every five minutes, I went back and asked if he wanted a menu.

He declined and glanced at his watch again. I commented on his watch about how I liked his use of "analog technology". He laughed nervously and said he didn't want to pull his phone out during his date. He didn't want to seem disingenuous. Another half-hour passed, and he was still by himself. I offered the menu again.

But he just shook his head defeated. "I'll just finish my drink and go. Sorry I wasted one of your tables". On his last swig, a cute girl walked in looking around the room. My guy stood up and called her over excitedly. He was beaming from ear to ear. But when I looked over, I was horrified. She had a disgusted look of disappointment on her face.

She rolled her eyes, looked at me, sighed, and said, “Are you kidding me with this guy?” Then she screwed on a fake smile and immediately sat down, avoiding his half-hug attempt. The whole date felt forced. Every time I went to check on them, she was ordering another drink. He tried his best to get a conversation going.

Except she had her face in her phone the whole time. An hour later, I watched the girl get her purse, announce she was going to the washroom, and walk in its direction. I immediately walked over and asked him how his date was going. He told me that he didn’t think she liked him. I gave him a reassuring pat on the back.

I told him that he was doing everything right. He smiled and thanked me, and I went back to the bar. She never came back. He paid her tab—$90 worth of drinks. His two drinks were $8. He continued to come back as a regular, and I became his wing-woman. I eventually set him up with somebody, and they’re still together.

Waiters awkwardPexels

5. Customer Loyalty

A guy named Greg came into the restaurant very well dressed, and I sat him at a table. He told me that he was meeting someone for their first date. About half an hour later, no one had arrived. It was a slow Sunday night, so I checked on him. He hadn’t heard anything from her. Another half-hour passed, and then another.

He finished his meal, paid, came up to me, and said, “I guess she’s not coming. Whatever". I tried to convince him to wait at the bar a little while longer, but he was not having it and left. 20 minutes later, a girl showed up. She told me that her phone ran out of battery and her car broke down on her way to meet Greg.

I told her that he’d gotten fed up and left. She started crying because she thought she really messed things up. But I reassured her because he signed up for the rewards program, and we had his number. Officially, I wasn’t supposed to do it, but I called him up and told him that his date was here. He didn’t believe me.

So, I gave her the phone, and he came back 20 minutes later. They seemed to really hit it off, and as he left, he said, “Thanks, man,” and slipped me a $5 bill. They came again, and I was so happy that they kept dating.

Waiters awkawardShutterstock

6. Two For One

There was one year when I worked at a Mexican restaurant and had to watch one of the weirdest first dates ever on Valentine’s Day. The couple walked in, and the woman was dressed to the nines, like she was ready to hit up a club. He’s more casual in jeans and a button-down shirt. The hostess walked them over to their table.

I went over and greeted them. The man announced that this was their very first date. The lady looked less than impressed and forced a small smile. After I brought them their drinks, I watched as their date became even worse. The guy was excitedly talking while the woman looked around like she’d rather be anywhere else.

I went to take their order, and it was obvious that I’d interrupted something. The guy looked a little embarrassed and sad, and she just looks angry and upset. He ordered his meal, and she glanced at the menu and ordered seafood enchiladas. She then tossed her menu in my direction and sucked down the rest of her drink.

I brought their food and went behind the counter to roll silverware and keep an eye on my tables. They dug in, and he seemed to be enjoying his food. Her behavior, on the other hand, was atrocious. She looked disgusted and was flicking bits of her dinner everywhere. I went to see if she wanted to order something else and asked how everything was.

The woman stood up and started screaming how her food was gross and how awful the date was going. She shouted at him about how he should have ordered for her, how dare he bring her to such a low-class place, and how done she was with him. She then left the table and stormed out of the restaurant. The guy was mortified.

I told him that I’d be right back with his bill and asked if he wanted his food to be boxed up. This guy shook his head, grabbed her plate, and said he was fine to keep eating what he’s paying for. He stayed and finished both meals. We talked about that couple for weeks after.

Waiters awkwardPexels

7. Young Love

I was waiting on a teenage couple who looked about 14. They were sharing their ice cream and holding hands really awkwardly. And when they were finished, all they talked about was their hormonal-fueled, adventurous fantasies. I felt very awkward when I had to interrupt them to ask if they wanted to order anything else.

Waiters awkwardPexels

8. Credit Where Credit Is Due

At the end of their date, the guy’s card declined. Trying not to embarrass him, I waved him over. He told me to try it again, and I assumed he was going to move money with his app. He went back to his date. It declined again. The machine printed a receipt that read, “insufficient funds". But I tried it four more times.

I finally went to the table and said that I was having an issue with his card and if he had another. I walked away with a new card. It declined. I waved him over again. He stood up angrily, and I could tell that his date was catching on. He then berated me about how it was our machine’s fault because he did have money.

Then he started questioning if I knew what I was doing and making fun of me. He gave me another card. It declined, and his date paid.

Waiters awkwardPexels

9. Can’t Look Away

The couple sat down, and the guy was staring at his phone the whole time. I usually waited until people are off their phones, but he wasn’t showing any sign of putting his down. So, when I took their order, he just held his hand over his phone and talked over his date. When I came back, she tried ordering an appetizer.

He tried telling her that the portions were large enough without it. She got it anyway. I brought out their appetizer, and at this point, there hadn’t been one time when I saw him off his phone. While I was putting together the salad, the woman came out to the lobby. She asked to have her meal packed and paid her half.

Before she left, she told me that it’d been their first date that a soon-to-be-former friend set up—a friend who she would be calling soon. When I brought the guy’s meal to him, he asked where her dinner was. I told him what happened. He really thought she’d been in the washroom…

Waiters awkwardPexels

10. Low Face Value

A couple of years ago, my husband and I were on a date in London for my birthday. It was our first proper date since becoming parents. We caught a matinée and then went to a restaurant near the movies for dinner. Early on into our meal, we realized that the couple next to us was on their first date, and to say it was awkward…wouldn’t do it justice. 

The guy was clearly full of himself but then had this horrible move of leaning over the table and stroking the poor girl's face. I think he was trying to be sensual, but it just looked uncomfortable. The girl was just trying to get through the date, and he kept stroking her face from her eyes and then down to her chin.

Waiters awkwardUnsplash

11. Full Of It

I used to work at a sushi restaurant in Anchorage, and there was a girl who would come about once every few weeks with a different guy. Every single time, she ordered a hoedeopbap, which is like a rice-salad-sashimi bowl, and it was just huge. I’ve only ever seen a couple of people finish the whole thing in one sitting.

This girl always finished it and got a spoon at the end. It was always fun watching the guy’s stunned face when was done. Once, she came with this guy who ordered what she did. And when they both finished the bowl, they ordered another and shared. I wish they’d ended up together, but she later came back with a new guy.

Waiters awkwardPexels

12. Don’t Mind Me

I worked as a barista at a coffee shop that had a dishwashing sink, which meant you were face to face with whoever was sitting at the coffee bar across from you. For some reason, a lot of people chose this spot for their first dates. So, I was forced to wash dishes and pretend I wasn't literally on the date with them.

One time, a person I knew was on their first date with someone and chose that cursed seat across from the dishwashing sink. We chatted for a little bit, and then, as if a partition raised between us, they began their date. Except there was no partition; I still had to stand there to do the dishes. It was uncomfortable.

Waiters awkwardUnsplash

13. Doesn’t Sit Well

I was serving two people who were on their first date. But after the appetizer, the poor man started having stomach issues, and he was running back and forth to the washroom all night. There were only a few other people there at the time, so everyone noticed. They chuckled every time he stood up. I felt so bad for him.

Waiters awkwardPexels

14. Seeing People Differently

The guy was going on about how nice modern dating was without always needing labels. The lady, in a forced chipper voice, responded by saying that labels help to define relationship boundaries. In a similar but slightly louder voice, he said that it was nice to enjoy time with someone without having to define anything.

It was so hard for me to listen to them. I wanted to jab a fork in my ears.

Waiter awkwardUnsplash

15. Previous Engagements

It was a Valentine’s Day date that seemed to be going well and wasn’t awkward. They talked non-stop with no lulls in between. They laughed and had a great time. In fact, another server and I were laughing about how loud they were being. But then I heard the guy say something so jaw-dropping, it’s unforgettable. He goes, “...and obviously you’re not still married...right?”

“Please tell me that you’re not still married". There was an awkward pause then she said, “Well, actually…” The mood changed in an instant. It must not have been a deal-breaker because they stayed at the restaurant another hour until we closed, but they were very quiet for the rest of the night and hardly spoke at all.

Waiters awkwardShutterstock

16. Take My Seat

I was the one on the first date. We went to a bar, and when the waitress came up to take our order, she immediately recognized him. She was a bit too friendly while writing down our orders. When she left, my date told me that they used to date. They spent the rest of the night openly flirting. There was no second date.

Waiters awkwardPexels

17. Who’s Boss

I was working at a high-end restaurant as a busser for a while and eventually got a chance to work in the bar area while a jazz band played. Most of the tables had just drinks and appetizers. On my first shift, a woman in her 40s came in with a tall, dark, handsome guy who was no older than 30. Nothing wrong with that.

But all of my interaction with them was the woman talking down to me on some sort of power trip and her ordering everything for her date. They had cocktails, ordered a bottle, and had multiple entrées. She ordered ahi tuna, RARE. She was very insistent on the rare, so much so that I entered blue rare into the computer.

She sent back four plates that were “too well done” to the absolute horror of her date. I informed her after the second that they wouldn't be taken off her bill, and she scoffed and made some comment about how she was loaded and it didn't matter. She sent her last order back and asked to have a shrimp cocktail instead.

I left them to enjoy the music, brought the check, and when I came back to pick it up, her date wasn’t there. All his things were gone, and he was nowhere to be seen for 30 minutes. But the ordeal wasn’t over yet. She apologized to me and asked if I could take the $45 ahi tuna off of her bill. I told her to kick rocks. Not really, but my manager did.

The next day she wrote a 500-word review about me, using my first name, on the restaurant’s Facebook page. My boss printed it out, framed it, and I still have it today.

Waiters awkwardPexels

18. So Close

After appetizers, two expensive entrees, drinks, and dessert, the man asked me in front of his date, “Hey, we’re on our first date. What more can I do to guarantee I get [lucky] tonight?” The young lady turned deep red, and her jaw dropped. I put down the bill and said, “After asking that? There is nothing you can do".

Waiters awkwardShutterstock

19. Free To Go

I wasn’t the waiter in this case but only a nearby patron. There was a couple on a first date close to my table. And when they were just about done with dinner, her phone rang. She answered it and told the person that she wasn’t busy and made plans to spend the night with him…all the while her date’s jaw was the floor.

Waiters awkwardPexels

20. Romance Vs. Bromance

There was this couple on a date who had shown up separately. The first few minutes were awkward but cute, and the rest went on fine. Then this guy came and sat down on the stool next to the guy on the date. This guy was a huge guy’s guy. He and the guy on the date got to chatting within minutes and were really bonding.

For the rest of the night, the woman on the date just looked at her phone while the two guys had the time of their lives. After finishing her meal, the woman said goodbye and got an Uber home. Her date could not have been less phased. He and his new best friend hung out drinking until closing time, stumbling arm in arm.

Waiters awkwardPexels

21. Table Top Of The Line

There was a lady in my section by herself. She was just waiting. This woman was absolutely gorgeous. I ended up talking to her a bit because she was obviously bored. She was smart and seemed like she had a pretty good sense of humor. She was telling me that she was there to meet some guy on a blind date. I was shocked.

I thought, "What kind of jerk would leave a woman like this waiting?" A complete loser, as it turned out. The guy eventually came in looking messy, even though it was fine dining, and acting all cheekily. The woman confronted him about being late. His reaction was truly deranged. He responded by getting on top of the table and addressing everyone in the restaurant.

He asked if they thought she should forgive him or not. Everyone ignored the guy except for the one guy who said, "Get off the table, dude". They talked for a bit, and then the guy went to the washroom. I went to her table and said, "You don't need to pay for your drinks or anything. If you want to leave, you can now".

She said thanks but ended up going ahead with the date. They left my section and went somewhere else. Honestly, the thought that that guy actually got away with a cringe-inducing stunt disappointed me. I wanted her to ditch the guy so bad.

Waiters awkwardPexels

22. How Claw-dorable

A young couple was at my table. Both were probably 16. She was overdressed for Red Lobster and a movie, but it was cute. He went to pay, but his card was declined. I felt so horrible walking back to the table. He said that there should be enough in his bank account. I asked if he had put gas in his car before the date.

He nodded. Some gas stations hold twice the amount on a debit card after a certain hour which drops off the next day. The poor kid was so embarrassed, and he had no idea what to do. My boss paid for his meal, my tip, and gave him money for the movie they were planning to go see. He paid him back in full two days later.

Waiters awkwardPexels

23. Getting A Good Feel

I wasn’t a waiter but just happened to be nosy. I was with my friend to this Italian place where we always went in high school. This one guy came in and sat down at a table. He was looking around and at his phone like he was waiting for somebody. When the waiter greeted him, he chose a bottle and asked for two glasses.

Ten minutes later, his date finally arrived and sat down without saying a word. He didn’t say anything either. They silently sat and drank from their glasses. These two people in their 20s were sitting there like old people who have nothing to talk about after being together for 40 years. They both ordered the ravioli.

When it came out, the guy grabbed his ravioli with his bare hands. The woman didn’t touch hers and watched as the man licked sauce off his fingers one after another. My friend and I were convinced she was trapped on the worst first date ever. Except, to our surprise, we watched as she grabbed her ravioli with her hand.

She sucked it down and got sauce all over the place. We couldn’t figure out what was happening. And they both still hadn’t said anything that entire time. They ended up ordering a cake for dessert and ate it with forks.

Waiters awkwardPexels

24. Big Mistake

At a restaurant where I worked, there was a white guy and a black guy on a first date. They were sitting in a booth and having a great time. The white guy got up and went to the washroom. When he came back, he made the most cringeworthy mistake I can think of. He went to the wrong booth, where a different black guy was sitting.

It took him a minute to realize it was a different person. His date was not happy at all. They tried to salvage the date, but it didn't work.

Waiter awkwardUnsplash

25. Poor Interfacing

In a restaurant in Canada, a couple came in from the States. The man had the first generation iPhone, which hadn’t been released in Canada yet. A guy at a nearby table was so enthralled with it, he could not stop talking to him. They talked so much that his date just got up without saying a word and walked out the door.

Waiters awkwardPexels

26. Dashing Dine

There was one guy who was notorious for coming into nice restaurants and bars on first dates. He was legendary. And one day, he walked into the restaurant where I worked. He walked up to the host and told her that he needed a table for two. At that time, there were only about five tables dining, so it was pretty quiet.

As he waited, one of my coworkers came up to me and asked, “Isn’t that the guy from Burbank?” It was that guy from Burbank. He gained his infamy from pulling off the same stunt all over the city. He was known to meet women who he met online and take them to a nice place. On the date, he’d order anything and everything.

After running up the bill, he’d ditch these women, sometimes in tears, to deal with the expensive tab. People in the industry had seen it happen and warned everyone else about his scheme. He was so infamous that there was a Facebook page dedicated to him with his picture and name. He was probably scoping out our place.

But we weren’t going to have it. We told our manager, an ex-bouncer, what was happening. He saw the Facebook page and the guy’s unmistakable gigantic forehead in the pictures. So, he wanted to kick this jerk out.  He went over, put both his hands on the table, and said to him, “We know who you are and why you're here".

“That’s not happening here. You're leaving". The guy looked stunned. Playing dumb, he said "I'm a customer. I'm here to give you business". My manager said, "We don't want your business. This is the last time I'm gonna tell you, next time we will be calling the cops". The man started walking towards the front to leave.

But then my manager grabbed him by the arm. He pointed him to our side exit away from the people and told him, "That's your door". The guy left, and we all vibed for a while in the euphoria of justice. The guy went on to keep doing his scheme until he finally got caught.

Waiters awkwardPexels

27. Something Better

This couple came in, and their chemistry was weird all night. The guy was trying way too hard to impress her by acting like a jerk while she looked like she was just pretending not to hate it to get the date over with. When it was over, she told her date that she was taking an Uber home. He awkwardly left without her.

She then waited for the bartender to come back over, ordered another drink, and asked him for his phone number.

Waiters awkwardShutterstock

28. First Date Tips

I waited on a couple who were clearly on a first date, and the woman was obviously not impressed by the guy who she was with. The date was over quickly enough, and the guy paid, leaving me a 5% tip. The next day, the lady came into the restaurant, walked up to me, and said, “That was the worst first date I’ve ever had".

She told me: “I was mortified when he stiffed you on the tip,” and then she handed me $20.

Waiters awkwardPexels

29. Waiting Game

One night, this cute girl in her 20s came in, ordered, and cheerfully asked if any of the board games were good for two people. I showed her a couple of games. She chose one and sat at a table by the door. Half an hour later, she came over and sadly asked if there were any games she could play alone, so I gave her one.

I also said that if her date didn’t come, I’d give her a drink on the house. Another 40 minutes later, she came back for the drink, and we just talked for a little bit. It was a busy night, so she went back to play by herself. Her date ended up showing up almost two hours late and was very rude. She even bought him a drink.

But he was not interested in playing the game or his date. So, he left early. She stayed a bit to talk with me as I was cleaning up. I offered her another drink and had one with her. She left really sad.

Waiters awkwardPexels

30. Sugar Caf-fiend

A lady who was a regular at the café where I worked came in outside of her usual teatime. Soon after, a guy came in, and they introduced themselves. He had coffee. She had tea. Except her tea had 12 sugars in it. Two hours later, I think the only time I’d heard him speak was when he first introduced himself to her.

Waiters awkwardPexels

31. Speak For Yourself

I was actually the line cook there. It was a typical Friday night with a busy kitchen. A server came in and asked if I spoke Chinese. When I said I did, he told me to go talk to some guests at a table. Well, I said that they’d have to wait because we were in the middle of the dinner rush. Things slowed down a bit later.

So, I followed up with the server who pointed out the table of guests that needed help. I left the kitchen expecting to translate something on the menu. At the table, a white guy was with an Asian girl. I asked them how I could help, and the guy asked me to translate a few things for him. It was mostly just small talk.

For almost 10 minutes, I translated their conversation back and forth. Eventually, the guy asked if she wanted to sleep with him. She asked if he had a girlfriend. At the end of it all, she turned his offer down, and it got pretty awkward. I slipped back into the kitchen as soon as I could.

Waiters awkwardUnsplash

32. Here For You

We had a regular who always sat in one particular waitresses’ section. He was always alone and would flirt with her constantly. She didn’t mind it as he was pretty harmless. Plus, he came at lunch and always tipped well. Then he came one day for dinner with a woman. They were both dressed up and clearly were on a date.

He sat in his preferred section, and it looked like he was trying to show off or make the waitress jealous. They even ordered by the bottle. But then, at some point, his date had ditched him. So, he decided to down the whole bottle by himself. The bar served him one more drink because they didn’t see how wasted he was.

They ended up cutting him off when he fell twice. At the end of the night, he started sobbing to the waitress about how lonely he was. We had to call him a cab.

Waiters awkwardPexels

33. Committed To The Game

I worked at a small pet store where a lot of first dates happened. It was a small town with not much to do, so people would look at the puppies together. One time, this huge guy walked in with a stunner and told me they were on their first date. His date was letting this Pomeranian puppy lick the makeup off her cheeks.

The guy told me that he wanted to buy the dog for her. I told him that puppies were a big commitment and asked if she even wanted a dog. He angrily stormed away and said he was getting the dog for her as a symbol of his love. His date just nervously said, “My parents won’t let me have a dog until I finish high school".

“And I’d have to move out too". So, this guy dropped to one knee and said to her, “Move in with me". The cringe shattered the whole vibe of the entire pet store. Even the birds were silent. She put the puppy down and walked out. The guy turned the deepest shade of red that a human can become and stumbled out after her.

Waiters awkwardPexels

34. Bumpy Relationship

I was a server for a bit, and one of my coworkers always brought his first dates to our fancy restaurant. It was purely for the employee discount. But things got tricky when he started seeing another server. It was always entertaining watching her serve his first dates their fries during their first few weeks together.

Waiters awkwardPexels

35. Down The Hatch

In college, I was a barista at a small coffee/juice shop. Every week, we had a specialty drink. And that week, it was an espresso spritzer with mulled mint and fresh lemon juice. It was a pretty challenging drink taste-wise. A couple met in front of the store and quickly introduced themselves. The guy was very nervous.

He was obviously trying to make a good first impression and claimed to be “adventurous” and ordered the special atrocity. I gave him the standard warning about how espresso spritzers just are not for everybody, and I’d remake it if he hated it. However, he insisted that he liked “fresh mint". So, I prepared it for him.

I keenly watched for the exciting first sip. The look on his face was truly spectacular. It was a journey watching him process the shock and disgust. And then finally, dread was written all over his face when he realized he was going to have to drink the whole thing or look like a jerk who demanded his drink be remade.

So, I spent 45 minutes watching this young man suffer through an otherwise pleasant date choking down a disaster of a beverage. That made working in customer service worth it for me.

Waiters awkwardPexels

36. Getting Colder

I was bartending at an upscale place on New Year’s Eve. The couple sat down, and the guy got wasted and went to the washroom. When he came out, he was holding his phone open to his ex’s Instagram profile. He asked his date if she thought that he was hotter than his ex’s new boyfriend. His date kept trying to give him an out.

But the guy kept doubling down and said things like, “Well, I think you’re hotter than her, so why can’t you just say it to me".  The night ended with her waiting outside crying at 2 AM for her mom to pick her up. It was pretty hard to watch.

Waiters awkwardPexels

37. Resettling Down

There was a woman at the bar who was speaking unnecessarily loud to her date even though he was inches away from her. After the usual ice breaker chit-chat, he apparently said something that she didn’t agree with. So, she paused and said, “Okay, I think we should probably start this over. Like actually reset the date".

Before he could finish asking what the heck she meant, she stood up, took three steps to the door, turned around, and walked back. She had her hand stretched out and reintroduced herself. The guy was like, “You’ve got to be kidding me, seriously?” She just said, “I’m glad we could try this place out. Great to see you!”

After an uncomfortable pause, he just said, “Hey? Have a seat". Their date was reset, and I was left to try my hardest not to cringe from the second-hand embarrassment. It was an awkward move at best, but the guy was willing to play along, so at least it worked.

Waiters awkwardPexels

38. Driving The Conversation

There was a middle-aged couple on a date. The man spent half an hour going on and on about the car he liked, how fast they were, and their maintenance challenges. He was non-stop every time I passed them. When I came to their table with their entrées, he stopped talking. In that pause, the woman finally said something.

“Well, I really like butterflies". He didn’t say anything, so there was an awkward silence. But then in no time, he went off until dessert about his cars. It was weird though. They ended up coming back two times over the summer.

Waiters awkwardShutterstock

39. Sorry To See You Go

It wasn’t really awkward between the two on the date. The woman was just being very demanding and rude…except it was only when her date wasn’t at the table. Like she was putting on an act for him. I knew just what to do to expose her. I came back with their food and offered a completely over-the-top apology for the “terrible service,” with a tearful garnish.

The guy looked at her in horror, asked what happened, and eventually left.

Waiters awkwardPexels

40. Cropped Out

I worked at a fancy French restaurant, and there was a Korean couple who came in one day. They sat down, spoke for a few minutes then ordered. After that, he did not say another word to her. He played Farmville for the entirety of dinner. Even when they got their food, he didn’t break eye contact with his phone screen.

I had never seen a woman look so bored, but she stayed the entire meal.

Waiters awkwardShutterstock

41. What’s There To Eat

I was on the first date and made it awkward for our waitress. I met up with a guy who was from another country. Neither of us is a native English speaker. I’m fluent except that I don’t really speak “food". Our poor waitress had to try and explain what all the menu items were. She got a pretty big tip out of it though.

Waiter awkwardPexels

42. Have No Say

I worked at a “fine dining” chain. And one night, an older gentleman in his 40s came in with an Asian woman. I had to check their IDs for drinks and saw that she was 21. The man told me that she was visiting from Japan, and this was their first time meeting. They had been dating online for two years. She didn’t speak a lick of English, and he could barely get out any Japanese.

He ordered two appetizers and four entrees because he wanted her to have our delicious Wyoming seafood. As the meal went on, I watched the woman become more and more displeased. She didn’t like any of the food and stuck with her mixed drinks. During their dessert, I had a moment to talk with them more, and he told me that they were going to get married someday.

He was planning on building her own darkroom because she loved photography. She may not have spoken any English, but she definitely understood what he was saying, and she looked very uncomfortable. All the color had drained from her face. She just kept shaking her head and saying, “no, no, no,” as she stood up to leave.

He paid in a hurry and left four plates of half-eaten food running out the door after her.

Waiters awkwardPexels

43. Love Don’t Cost A Thing

I worked as a barista, and this couple came in on what looked like their first date. The girl was average-looking, and the guy was a complete hottie. The girl looked obviously nervous. So, they ordered coffee, and she grabbed a pack of nuts. She paid, and as I was getting her change, she poured her snack into her hand.

I had her change ready and then held it out for her. She put her snack pack down and held out her hand to take it. I dropped the change into her palm. So now, she was standing there with one hand full of change and the other full of snacks. I’ll never forget what she did next. Without missing a beat, she threw a handful of dirty coins into her open mouth.

Her eyes got as big as the coins in her mouth that clanged on her molars. She spat out the coins, and her face was beet red. I turned around because my face was probably showed a huge grin, and my eyes were watering. I didn’t laugh, but my co-worker Andre burst into laughter. Her date pretended he hadn’t seen anything.

Waiters awkwardPexels

44. Swimming With The Fishes

We had a rather unattractive older guy come in with a really good-looking blond girl. He was wearing a crazy colorful Hawaiian shirt. She ordered a surf n' turf dinner and a plate of crab legs, which were our most expensive items. After finishing their meals, the woman disappeared ghosting and stranding her date there.

He hung around until after closing trying to get a hold of her but to no avail. When I left for the night, I saw him in the parking lot with a bunch of officers.

Waiters awkwardUnsplash

45. Grand Entrance

In the summer, a guy came to the bar where I worked to meet up with four different ladies from For one of his dates, he told everyone else at the bar that he was from His date was late that night, so everyone was concerned for him. He just told them to clap when she got there. She finally came in.

The entire bar clapped and cheered. She was horribly embarrassed.

Waiters awkwardPexels

46. Different Expectations

I met this guy in college on my first week on campus where I worked. He came up to me and asked for my number in front of all of his friends. I, being dumb and 18, gave it to him to save him embarrassment. But then the next day, I came out of my dorm, and he was waiting outside. I had no idea how he knew where I lived.

He’d never texted or called to ask. He said that he’d been waiting for a few hours outside to see if I wanted to have lunch with him. Again, I was young, so I just said yes to give him a chance since he’d waited for so long, but I was seeing major red flags. I wanted to eat on campus, but he wanted to go somewhere off.

He brought me to a nice family dining Italian place, which I had never been to before. When I looked at the menu, I saw that they only served one large entrée for the table. He asked me what we wanted to get for us. I suggested getting the lasagna, which was the cheapest entrée they had, and I wanted to split the bill.

When the waiter came to the table, the guy ordered my drink for me, the lasagna, and the chicken tortellini. Each entrée was meant to serve eight people. When the food arrived, he scarfed his tortellini down and then asked for the rest of my meal. I gave it to me him and watched in disbelief as he cleared my plate too.

The conversation was completely null, and the only thing he could think to tell me was how he was scared of his 12-year-old sister. Oh, but it gets so much worse. At one point, I glanced at him to see that he was making a really weird embarrassed face. When I asked him if everything was okay, he told me that he’d just passed gas and apologized.

I told him it was okay. It was weird, but everyone did it, and no one had noticed. Then, to my horror, he leaned over and let out the loudest and nastiest toot I’d ever heard. It was so bad that everyone in the restaurant turned and stared at us. Our waiter just stopped in his tracks and turned to get into the kitchen.

He just said, “Oops! It slipped". That was my cue to ask for the check. I told him that I needed to get back to the dorm. But he seemed shocked that I was ending the date so early because he’d had other things planned for the day. He wanted to get ice cream, watch a movie, go bowling, and then go back out to eat again.

I politely declined and asked him to bring me back to campus. As I was getting out of his car, he handed me a note and told me to text him after I read it. I took it and got inside as fast as I could. I was spilling all the horrible details to my roommate when he texted me, “Is that alright?” I wasn’t paying attention.

I thought he was asking me about the date, so I texted back saying it was fine. He replied thanking me over and over again and said he couldn’t believe I was okay with it. I pulled the note out finally to figure out what he was talking about. I couldn’t believe what I read. It was a typed note that had my full name on it and was full of bible verses.

In it, he said that he was a “second-chance virgin” and had lost his virginity to another woman. He asked me not to try and seduce him during our “relationship". I texted him saying that he had the wrong idea and politely told him to leave me alone. I mean he had forced me on a date, which never implied a relationship.

Two weeks later, he texted me again asking me to hook up before he left town. So much for being a “second-chance virgin".

Waiters awkwardShutterstock

47. Sweet Ice Breaker

In high school, I was waiting tables at a restaurant when a couple on a first date came in. They weren’t really talking, and it was painful to watch. The woman asked for a refill of her iced tea, and I grabbed the pitcher to fill her cup. But as I was pouring, I dropped the entire pitcher of sweet, sticky tea onto her.

It went down her shirt, her skirt, everywhere. She was completely and utterly soaked. My newly blossoming career as a server flashed before my eyes. I apologized profusely and brought over 4,000 napkins so she could wipe up. Her date the whole time just stared and looked dumbfounded. She cleaned up as best as she could.

Then their date continued, and they ate their meals. Magically, they started talking and looked at each other just like a new couple would. They laughed and enjoyed their food. An hour later, they left the restaurant with her arm in his. They gave me the biggest tip I had ever gotten. I got a $20 on a $20 bill in 1996.

Somehow, my idiotic blunder turned the worst first date ever into a good one. I like to imagine them now as a happily married couple with seven kids who they love telling the story of the dummy who poured an entire gallon of tea on her on their first date.

Waiters AwkwardUnsplash

48. Big Talker

In college, I worked at a pub connected to a brewery. This guy came in one time with an absolutely gorgeous woman. They were at the end of the bar, and the guy was going on loudly about how he had a room for them next door at the hotel downtown. They then decided to go to the brewery next door and pull a dine and dash. Huge mistake.

What they didn’t know was that everything used the same system. So, when he ordered more drinks, the bartender asked him if he wanted to add them to his tab. He looked confused and said, “What tab? I’ve never been here". She printed the receipt with his brewery tab which was about $80. All he could do was stare at her.

Then he flew off the handle. At the end of it, the woman ended up having to pay for it. They walked across the street to the hotel where he’d already invited her. But she stalled until her ride came and just left him standing there.

Waiters awkwardPexels

49. Get Out When You Can

I was working at a high-end steakhouse when a couple came in on a first date. The man was friendly and seemed like he had good taste. He ordered a fairly expensive bottle. As I was presenting it, the woman's phone rang, and she picked up. Apparently, her close friend just broke up with her boyfriend and was distraught.

The woman asked if her friend could join them for dinner. The man said, "Of course," and was really gracious about it all. The friend showed up within a few minutes and was a crying, hot mess. I brought her an empty glass then, before I could pour it, the first woman grabbed the bottle and filled the glass to the brim.

And then she ordered another bottle. After I opened it, the man excused himself to the restroom. While he was away, I overheard the friend expressing concern about the menu prices. The first woman said, "Get whatever you want, I'm not going to ever see this loser again". So, I came up with a plan. I caught the man coming out of the bathroom.

I told him what I’d just heard. He asked me what he should do. I told him that he was welcome to leave through the delivery door in the back and I would play dumb for his date. The guy expressed his gratitude by tipping me $100 on his way out. Back at the table, the woman became increasingly irate as the night went on.

She knew the man wasn't coming back to pay for their food. But she waited until closing time before settling the drink tab and leaving hungry in a taxi.

Waiters awkwardPexels

50. Unexpected Company

I was a waitress at a small-town restaurant. A grown man in his late 30s came and told us which table he wanted and that he was there for a date. He described what his date would be wearing and sat down. His date came but wasn’t as expected. It was another grown man who was wearing the bracelet the first man described.

I brought him to the table. When we got closer, they made eye contact and almost in unison said, “You’re actually a guy?” Well, they had dinner and talked the whole time. The story behind their “date” was insanely creepy. Apparently, they both pretended to be women interested in women online to try and find hot younger girls to date.

Waiters awkwardUnsplash

Sources: Reddit,

More from Factinate

Featured Article

My mom never told me how her best friend died. Years later, I was using her phone when I made an utterly chilling discovery.

Dark Family Secrets

Dark Family Secrets Exposed

Nothing stays hidden forever—and these dark family secrets are proof that when the truth comes out, it can range from devastating to utterly chilling.
April 8, 2020 Samantha Henman

Featured Article

Madame de Pompadour was the alluring chief mistress of King Louis XV, but few people know her dark history—or the chilling secret shared by her and Louis.

Madame de Pompadour Facts

Entrancing Facts About Madame de Pompadour, France's Most Powerful Mistress

Madame de Pompadour was the alluring chief mistress of King Louis XV, but few people know her dark history—or the chilling secret shared by her and Louis.
December 7, 2018 Kyle Climans

More from Factinate

Featured Article

I tried to get my ex-wife served with divorce papers. I knew that she was going to take it badly, but I had no idea about the insane lengths she would go to just to get revenge and mess with my life.

These People Got Genius Revenges

When someone really pushes our buttons, we'd like to think that we'd hold our head high and turn the other cheek, but revenge is so, so sweet.
April 22, 2020 Scott Mazza

Featured Article

Catherine of Aragon is now infamous as King Henry VIII’s rejected queen—but few people know her even darker history.

Catherine of Aragon Facts

Tragic Facts About Catherine of Aragon, Henry VIII’s First Wife

Catherine of Aragon is now infamous as King Henry VIII’s rejected queen—but very few people know her even darker history.
June 7, 2018 Christine Tran

Dear reader,

Want to tell us to write facts on a topic? We’re always looking for your input! Please reach out to us to let us know what you’re interested in reading. Your suggestions can be as general or specific as you like, from “Life” to “Compact Cars and Trucks” to “A Subspecies of Capybara Called Hydrochoerus Isthmius.” We’ll get our writers on it because we want to create articles on the topics you’re interested in. Please submit feedback to Thanks for your time!

Do you question the accuracy of a fact you just read? At Factinate, we’re dedicated to getting things right. Our credibility is the turbo-charged engine of our success. We want our readers to trust us. Our editors are instructed to fact check thoroughly, including finding at least three references for each fact. However, despite our best efforts, we sometimes miss the mark. When we do, we depend on our loyal, helpful readers to point out how we can do better. Please let us know if a fact we’ve published is inaccurate (or even if you just suspect it’s inaccurate) by reaching out to us at Thanks for your help!

Warmest regards,

The Factinate team

Want to learn something new every day?

Join thousands of others and start your morning with our Fact Of The Day newsletter.

Thank you!

Error, please try again.