50 Waiters On The Most Awkward Date They Have Ever Witnessed At Work

1. Couple came into the restaurant dressed very goth. I wasn’t their server but I was running the cash register just a few feet away. They proclaimed to everyone that they were energy vampires, but not to fear them because they won’t hurt us. They said they didn’t need our food for sustenance, but enjoyed the taste. After ordering the meal they then politely asked the waitress if she would stick around for a second so they could feed off of her aura so they could have enough energy for the night. The waitress said ok and gave me a side glance over her shoulder that I knew meant “I better get a good tip for this.” The couple clasped each other’s hands, closed their eyes, and made sucking sounds for a solid minute before leaning back in the seats and sighing as if they had just had a turkey dinner. The waitress was indeed tipped well for her delicious energy.

2. First date, I would estimate college age. They’re eating and the girl says, “I’m having a really nice time, but my friend just texted me and asked me if I wanted to hang out, and I said yes, so I actually have to go.”

3. A girl hit on me in front of her boyfriend when I was serving. The boyfriend walked off after staring her off and the girl awkwardly sat there alone for a while. I asked a ‘girl’ friend to take over her table, because it was too awkward.

4. I work at a dinner theatre, and we usually do proposals where we set up a ‘random draw’ where the ‘winner’ comes up on the stage to win their prize, and are then surprised by their partner who proposes. It’s usually sweet and makes everybody in the room all fuzzy and warm.

This one guy wanted to take it further and requested to perform a song — he brought his own music and everything. We’re pretty easy going at this job, so we agree to let him do it.

We do the fake draw, the woman comes up on stage infront of a room of 400 people, and the music starts to play. Apparently this guy was a little nervous, and he compensated by having a few drinks. So what follows is a slurred performance of a song written by this guy, that seemed to focus on how he was sorry for cheating on this woman with her sister and at the end of it, he gets down on one knee and proposes. Usually this gets a round of applause, encouraging the person to say yes; but not after that trainwreck of a performance. The poor woman was just holding her face the entire time and starts shaking her head and says “No, what’s wrong with you?” She storms off and leaves him and our stage manager on stage to a bunch of murmuring from the audience. The only thing our stage manager can think of to say on mic is “Well, that’s that.”

The guy ended up staying for the rest of the show and had many more drinks. That was years ago and it still remains one of the cringiest things I’ve ever seen.

5. When I was bartending this guy came into the bar on a week night, average looking guy, late twenties. He sat down and asked for a drink and told me he was nervous because it was his first date in 3 years and they had met on tinder. He arrived 20 minutes before her expected arrival to get rid of some of his nerves….two hours passed and he waited for her with no text or call explaining she would be late.

This woman walks in, walks up to the guy and I’m thinking “wow! She really came! “ . She looks at him and says, “Are you Joe?” The guy replies yes and gets up to properly greet her looking incredibly excited… She says, “No thanks…” and just leaves.

What a foul creature. Joe(not his real name) and I proceeded to get way too drunk for a Tuesday. Poor average Joe.

6. Husband and wife fight. Wife cried. Husband got up and threw a pizza slice at her face.

7. Date seemed going well, but the guy was nervous and fidgety. He was rocking back on his chair a little as he would talk and eventually flew too close to the sun. Toppled his chair backwards and knocked himself out cold. And peed his pants.

He had to be taken out of the dining room on a stretcher over the span of 20 minutes, while his Tinder date did the honorable thing and immediately went to the bar and ordered shots.

We gave them to her on the house.

8. I guess you could call this a couple date. I was working at a wine bar when a married couple sat down on a pretty slow night. I went over the specials and they ordered. Once appetizers came out the man thought it would be a good idea to serve his wife divorce papers. I did my best to avoid that side of the bar. I did bring out tissues for the wife who was breaking down. I ended up boxing up the dinner. The guy paid but I do not envy that ride home.

9. Served a deaf couple having a fight. They went from both of them signing furiously to her crying and signaling to me for a stack of napkins for, I assumed, her tears. She whips out a pen and starts writing paragraph after paragraph angrily. It was awkward because I kept having to come back to the table since they ordered multiple courses and he was just eating and signing while she was hunched over the table writing away while crying. When they finally left they tipped me pretty well though so I guess it wasn’t too bad?

10. Had a couple come in one night and everything seemed to be going fine. We just hired a new sever who was training and I asked her if she had any questions. She was still nervous about greeting tables so I told her she could shadow me and watch what I do. We go over to the couples table and all I hear from the new server is “YOU FUCKING BITCH I KNEW YOU WERE CHEATING ON ME”

Turns out the guy was her bf on a date with his side chick and he didn’t know she just got a job there. She didn’t get fired for what she said.

11. One of my first jobs in New York was managing a lounge/cocktail bar in a high end hotel. At around 3 or 4 o clock, a guy that looked pretty cheesy (slicked back hair, bad suit etc.) came up to me and demanded that he get that window table tonight for his date (he had a reservation for 8pm). I explained to him that I can’t guarantee it etc etc and he slipped me $400 with the “How about now” look in which I eventually caved in and told him that I’d take care of it.

He then pulled another stack of hundreds and started counting them in front of me while asking if I could go a little extra by coming over to the table when he was there with the date and pretend that I knew him from a movie. At this point, if I’ve gone this far, why not?

Sure enough he rolled around later in the evening with a blonde bimbo and after they’d had a glass of champagne I approached the tables around them, checked on how they were doing before going over to him and did the whole “How are you enjoying your evening?” And before walking off I did an Oscar worthy double take with a “are.. are you… by any chance..? You must be..” at which point he had this douchy smile lapping up the “recognition” he was getting from this young dude he’d just paid off. Most importantly for him though, it worked – she was loving it – and they left shortly after and he slipped me another $600 on the way out.

12. There was a couple at my work having drinks, girl went to the toilet, came back and admitted that she’d been sleeping with the guy’s brother. Apparently glasses were thrown across the room and they both got kicked out.

13. Really little guy, maybe 5 foot 4, 120 pounds comes in with a gigantic woman, probably 6 feet tall and easily 300 pounds. Both tatted the fuck up with piercings to match.

The woman orders her dish and before I get the guy’s order, he says in a sexy voice, “I think you want more than that.” She smirks at him, says, “You know I do,” and orders three more entrees. This was clearly a thing for them. They seemed incredibly happy together and became regulars at my restaurant.

I feel like I played a not insignificant role in this bizarre couple’s eating fetish for like three years.

14. A girl brought two tinder dates and played them off each other game show style. They seemed to be unaware this was what would happen. Splitting the bill was hilarious.

15. This trashy couple I served were disgusting people to begin with and to top it off the woman was trying to be sneaky and jerk him off under the table.

Unfortunately I saw this happening and just pretended like nothing was happening because I didn’t want to deal with it

16. Was a bartender/waiter a few years back and I was delivering some food to a table to find out that it was my ex and her new boyfriend sitting at the table. We had only stopped seeing each other a month earlier so it was incredibly awkward for everyone.

17. Working at a chili’s on Valentine’s Day, the girl gave me her number with her boyfriend in the bathroom, I came back and had to deal with her being sweet to him and nice the rest of the dinner. I did not call or text her, just was weird every time she’d look me in the eyes following.

18. There’s a habit of some older couples where the elderly gentleman will order on behalf of his wife. I guess it might have been cute and romantic once, but it doesn’t work with some younger couples.

I was serving a younger couple (early 20s), who seemed pretty early into the relationship. They were ordering drinks and he orders her drink for her. Far from being dazzled by him knowing what she wanted, she didn’t want any of it

“Well I’d actually like a latte, not a coke. But fine whatever, if I don’t get a say…”

He responded quite angrily with, “Oh sorry, have what you want then!”

She got her latte and he glared at me. They ate and left. Not been in since, I’m sure they’re doing well.

19. I’ve witnessed countless of extremely uncomfortable dates where the man will not shut up about himself and the woman sits there awkwardly nodding waiting to GTFO.

20. I had this girl one day on lunch date (or so I thought) with this other girl. Thought nothing of it, maybe they were together maybe they were not.

Well I had one of the girls sit in my section again…. with another girl. Thinking nothing of it, I ask if she is the same person that I served a few days ago. Her eyes turned giant and the girl she was with laughed nervously, “Oh, you came here without me.”

At this point I caught onto something so I tried to save it by saying it must have been someone else, I get so many people some days. I’ll never forget those eyes piercing through my soul telling me to shut up.

21. Looked like it was a married couple and at one point I heard the husband mention he wanted to get a divorce. The next time I came around the wife had turned her chair around, facing away from the table, with her plate in her lap. She asked me for the ticket while the husband was desperately trying to get her to turn back around and talk to him without causing a scene.

22. When I was in school this old guy used to bring in all these different young ladies. I thought they were his daughters until one day I noticed lots of touching. later found out he was paying for “escorts”.

23. Older couple was having lunch at our cantina, when a younger woman who I assumed to be their daughter showed up. I was coming to greet her and bring chips and salsa when she suddenly grabbed the man’s frozen marg and threw it in his face while shouting, “If you’re gonna have lunch with your wife then you should stop texting me!!”

Needless to say I had their food made up to go…

24. I was presenting a bottle of wine to a first date and poured the guy a taste. He spit it back into the glass and said, “Delicious.”

25. I waited tables in Scottsdale, Arizona for a bit when I was in school and one night I had this married couple.

They were both in their late 20s or early 30s.

Anyhow, the guy starts to tell me about swingers parties around the area and how I should go.

Later in the evening, he asked me if I thought his wife was cute. I didn’t know what to make of it. She told me she that I was handsome and I was a bit naive and just said thank you and walked away.

Now that I am a bit more experienced, I am pretty sure he wanted me to bang his wife.

26. This awkward, middle-aged guy shows up 45 minutes early for his reservation, so he gets seated anyway since we weren’t busy. He brought a book with him, and refused to order anything until his date arrived.

His date arrived 15 minutes after the reservation. It’s clearly a blind date from a dating app. She sits down, refuses to order anything.

I left them alone and for the next 15 minutes, she looks like she’s interrogating the guy. She eventually gets up and leaves. It appeared she was not wasting her time with a full date when she could rush the experience and get on with her life.

The guy looked devasted, so we offered to buy him dinner. He declined and left the restaurant in the saddest way possible.

27. I was a bartender, and helped get two strangers (man and woman) chatting across the bar. They hit it off, talk a lot, clearly into each other. They moved closer, I turned away and was helping other customers and not paying much notice. Eventually I realize that he is now standing behind her with his hands up the back of her shirt, giving her a sensual back rub while her eyes are closed and she’s moaning softly. This was at lunchtime.

It went great for them, but was awkward as fuck for everyone else in the bar.

28. After they ordered, she got up and left the table. And she never came back. Food arrived and he said to box it up.

29. Once had a blind date while I was working At an upscale Italian restaurant. The lady came in early, younger and a little on the heavy side to put it nicely. She ordered a mixed drink, and almost chugged it, she drank it so fast. About twenty minutes goes by and I’m worried she is going to be stood up. Finally a guy comes rolling in, in a very quick manner like he knew he was late. He is tall and fit and doesn’t look like he has trouble finding dates. I’m a little worried that he won’t find the nice young lady suitable. But boy how I was wrong, and a fucking dumbass for think these things. They hit it off, talking and laughing all night. They pretty much close the place but weren’t being rude and staying too late after we closed. They eventually work their way out the door. And here comes the kicker, I go to take some trash outside to the can, and they are sucking each other’s faces like there is no tomorrow in the lot, propped up on one of their cars. I go inside to share the news with the staff that the date was a success, they were feeling the same way I was about the whole thing. We are all excited too. Figured they went home and shagged it out. Anyway about thirty minutes goes by and me and the waitstaff are leaving through the back door. AND WHAT DO WE SEE? The fucking car they were kissing at is now fogged the hell up and bouncing up and down in our parking lot. It was the funniest way this night could have ended. Moral of the story, don’t put judgments on people’s looks, and always try to shag on the first date.

30. I was eating at a restaurant and heard the hostess ask a couple she was seating if they were out for anything special. The husband replied, “No, it’s just our anniversary.” It has inspired my father in law to drop that line almost anytime he goes out to eat now.

31. I waited tables at this restaurant that had a big aquarium in the center. Like floor to ceiling huge.

A mixed age couple comes in and they’re nice but the guy is super quiet and nervous. Orders a whiskey straight but you can tell he really doesn’t drink, maybe sipped it twice. His date was probably 20 years younger and she seemed like she liked to party. She ordered two shots of patron right from the start and took them both.

Another younger couple was sat next to them and staring at the aquarium. Part of the deal there was having to talk about the aquarium and fish while people ordered. If I was busy I’d try to speel two tables at once with the aqua script then make a few jokes and fuck off.

I got both couples interested and talking then told them both I would be back. After I dropped the apps for both tables I see the young girl still talking with the younger table and they decide to push the tables together and eat.

The whole time the older guy is just smiling but I could tell he doesn’t feel comfortable. He barely touched his food and was just a fly on the wall at his own table. Eventually they decide to take the party outside to do some dancing. During the summer they give free salsa lessons and people have drinks and dance.

Maybe an hour later I’m taking a smoke break and I spot dude sitting on a bench crying. I walk up to him and give him a cig and try to talk to him.

Apparently his wife died about two year ago and that was his first time out since. He said he met that girl on some website and how she reminded him of her but she’s nothing alike and a bunch of really sad stuff. He said the girl left with that couple to go drinking and she just took off and left him alone.

32. There was a couple that came to lunch every day. And everyday they went to toilet together for like 20-30 minutes. So you can guess they had sex. It was inappropriate but we could nothing with that.

But one day she came to the restaurant with another man. And he was her husband. And that was a pretty awkward moment. So she started to come to the restaurant with her husband in weekends.

But one day, as usually, she came to us with her lover. They were arguing and as I’ve understood they broke up. She was crying an so on. After that fight I’ve never seen any of them.

33. This was just before Tinder and dating apps were a thing. It was a blind date, guy and girl. Guy shows up first and is excited, until he sees his date. She had their mutual friend show him an old photo of her because she had since gained significant weight. You can tell he was let down, but decided to make the most of it. They order drinks and appetizers. We didn’t even get appetizers out before the guy noped out of the date. He sat at the bar asking us to bring the appetizers to him there. Her weight wasn’t the only thing he was lied to about. Her personality and his clashed so hard the date didn’t last ten minutes. He hung out well after she left. We (the bar and wait staff) invited him to hang out with us at a bar after work. Ended up being a cool guy.

34. I had a middle-aged couple who seemed perfectly nice. The man asked me where he could go to smoke. I pointed him in the right direction and then started heading back to the kitchen which was in the same direction. He followed me and told me that the woman with him was his ex-wife. Not knowing how to respond, I said it was nice that they got along so well. He told me she just pretended to seem nice and was actually a terrible person.

I was feeling uncomfortable enough, but then he started to ask my age, if I had a boyfriend, what I was doing later. Thankfully, I could excuse myself to the kitchen. However, serving that table was awkward after that especially since she kept touching and complimenting him.

35. Had a few breakups occur. Those are super awkward. The guy bringing the girl to a public place so she won’t cause a scene happens quite often. This one time a guy did this with his girlfriend at lunch. She then starts bawling I mean WAILING and everyone around is looking in their direction at this point. She then quickly resorts to anger and then starts yelling at him, tells him to ‘have a great life you fucking loser’ and whatnot then proceeds to get out of the booth and her foot got tangled in her long purse strap and she falls and slams her head on the back of the booth corner and falls on the floor. She is now really wailing at this point since 20 people in the restaurant watched her do this and she ends up running out the front door. My co worker goes over to the dude and is like, ‘do you want your check?’ Since they already ordered the guy was like ‘naw bring me my food still and just box up hers for me, may as well have some lunch!’ He sat there and ate and didn’t seem too bothered by what happened. Just a weird situation. You never know how someone is going to react to a breakup in public.

36. Not technically a waiter, but I worked at McDonalds (one of the thankfully less trashy ones) and a couple came in. Woman sat down and the man tried to order. There was lots of umming and ahhhing at what he wanted to buy, he ordered two meals that we gave to him and he went and sat down. What followed was a 10 minute shouting match about how he wouldn’t take her on a ‘proper date’ and how he fucked up even a McDonald’s date. Guess he ordered the wrong thing.

37. I worked in a resort hotel, high end, I waited tables in the fine dining restaurant. It was pretty common for people to propose there, so much so that I had a system for the whole thing. One guy came in and wanted to do the ring in the champagne thing, and I talked him into doing a dessert alternative that doesn’t result in a sticky ring and champagne on the floor. Anyway, long story short. I bring the ring, she says “Dammit, I’ve told you before I’m not marrying you.” He flips, she’s super calm about it and basically treats him like a child having a tantrum, which to his credit he was not screaming or anything, just very upset. He left, she ate the fucking dessert, eventually he came back and paid and they left together. Super awkward.

38. I had a couple get in a huge fight while I was waiting on them. I tried to stay away from the table towards the end of the meal because the tension was so high. They were regular customers who I would see come in every few weeks, but I had never waited on them myself. At one point, the man gets up and starts walking across the restaurant to leave. The woman stands up and screams across a crowded restaurant, “AND YOU MADE ME STICK MY FINGER UP YOUR ASS!!!”

I never saw them in the restaurant again after that night.

39. They sat down and, from the girl’s body language, you could tell she was into him. As the date progressed she closed off, then sat pretty much sideways, then was playing on her phone. The body language shift occurred over maybe 1.5 hours. He didn’t stop talking the entire time.

She did give some nods and uh huh’s in response; even perked up a few times to contribute. But his monologue never stopped.

40. There was a couple sitting at the bar together – seemed like it was a first date. Maybe after 30min of them being together I’m in the back rolling silverware and the dude comes running into the back and goes, “There’s an exit back here, right?” and proceeds to bolt out of the back door.

We were all flummoxed. The girl sat at the bar alone for at least another 45 minutes before she left.

41. I worked at a fondue place. 1.5-2 hour meal for two people. Four courses, the works.

Couple came in and he had pre-arranged with us to present an engagement ring with the chocolate course with melted chocolate on the plate spelling “Will you marry me?” Also roses and other embellishments on the plate.

Apparently the entire meal she was explaining to him how bad he was at being in a relationship. Too needy, too emotional, somehow also didn’t spend enough time with her and wasn’t connecting with her? It was an hour long breakup speech.

We come around the corner with candles lit and the chocolate fondu and the engagement ring on the plate, the table next to them did everything they could to wave us off, I was holding a camera to capture the magical moment…which never came. He tried to get his prepared remarks out, but it was so bad we eventually left the dessert at the table and tried to act like nothing had happened. She left before the check came.

42. Served a young couple at a high end Italian restaurant that came in wearing matching outfits. I asked them what the occasion was. They were celebrating their 3 month anniversary. I’m so glad they found each other.

43. This wasn’t a romantic couple, but it was a father and his daughter. I thought everything was going fine but I could tell I was intruding in on times that they wanted to be alone, so I tried to adapt and stay out of their way. I don’t know what happened, but suddenly the daughter begins to cry and I had no idea until I approached and asked how everything was.

Immediately he looked annoyed, which was understandable, and I just left and didn’t talk to them for the remainder of their meal– including when I dropped off their food and got them the check. She cried the whole meal and it was a very emotional scene, and I’m not entirely sure what had happened except maybe a divorce or a death in the family.

44. When I was waitressing in college, I witnessed the single most embarrassing thing to happen to a person to date.

Right in the middle of their dinner (and in the middle of our Friday night dinner rush), this poor guy stands up, taps his wine glass to get everyone’s attention, and then proceeds to tell EVERYONE what a fantastic person his gf is, how much he loves her, and how lucky he is to have her in his life.

The whole time this is happening, she is just sitting there watching him with the most boring look on her face. It was so weird. Kind of like, ‘Yeah, tell me something I don’t know”.

Then poor guy pulls out a ring, gets on one knee and asks her to marry him. She gives him the most disgusted look imaginable and says “THIS is the ring you expect me to say yes to? Are you retarded? Could you be any cheaper?” Then she gets up and walks out, leaving the poor guy just kneeling there.

I didn’t charge him for the meal.

Edit: Just to clarify, this was a real rejection. Not only had they not even finished their meal when he proposed, a hostess at the restaurant knew the guy personally. Apparently it took him a really long time to get over it.

45. I was at one of these fancy speakeasy type bars they’ve started opening up installing a new invoice printer for their Point of Sale system. Waiting for the printer firmware and driver to install can take 30 or 40 minutes on slower computers, so I’m people watching.

As I’m standing there watching bars fill up, I notice a gorgeous blonde in her late 20s is sitting with a very well-manicured looking guy in his mid 40s. He’s dressed like he just left a high dollar law firm, and she looks like she’s going to a fancy professional cocktail party after their date. He is polite, talkative, and super into her, but you can tell that she isn’t reciprocating the feelings. To be honest, by the look on her face, she’s anywhere but in that bar at the moment.

The guy goes to the bathroom and she quickly picks up her phone and frantically calls someone and begs for pickup ASAP. The gist of the call was the guy was her mother’s coworker and her mother had set the date up, and our girl really wasn’t feeling it. About fifteen minutes later, a guy around her age comes in, throws some cash on the table and excuses them. She cites some vague emergency and is escorted out.

The older guy continues drinking ($140 tab, note that I’m standing at their main cash register) and starts flirting with the waitress, fails to get her number, pays in exact change without tipping, and leaves.

46. In law school I always worked the Sunday morning shift at the restaurant in town and it was always soooo dead but I’d bring homework so it was mostly ok. Every other week, this couple would come in and order G&Ts and nachos and sit for hours talking about how attracted they were to each other, their sex life, and would joke about sneaking around and what not.

I never thought much of it.

Until one day, I walked into the dining room from the kitchen and saw the lady had already been seated in a booth facing me. Her dude’s bald head was across from her, facing away from me.

I approached the table, about to ask the love birds if they wanted their usual, when the dude turned around and IT WAS A DIFFERENT DUDE. The lady looked at me sheepishly as he mentioned to me it was his WIFE’S birthday and they had never been at my restaurant before lmao.

47. I had a mid 40’s man with a young and attractive mid 20’s woman sitting at the bar. They were engaging in small talk and ordering drinks, nothing out of the ordinary. After possibly 45 mins a lady storms into the bar, and immediately goes up to them. She grabs the man by the shoulder and says, “You… You’re a cunt,” and walks out. The man turned to his perceived date and says, “Yeah, she does that,” and then left the room, leaving his date to sit there, staring blankly into oblivion until she left. Odd.

48. Not exactly a date- but I served a couple one time who had met up to discuss the terms of their divorce at the fancy-ish restaurant I worked at at the time. They came before the dinner rush so they were pretty much my only table, and every-time I’d check in on them the wife was extremely angry/tearful and they were bickering about holiday schedules for their daughter/timeshares etc. it wasn’t the end of the world but it was extremely awkward to butt in to change our their forks or refill drinks while they were so emotionally charged.

49. Was a cocktail waitress at a bar in a high-end restaurant a couple years ago. This couple comes in right around peak hours, guy looks annoyed, girl looks really excited. The whole time the girl is trying to talk to this guy and he’s completely ignoring her. He gets a call and talks on the phone for a good 10 minutes, hangs up and starts talking to anyone around him but her. He’s getting more and more drunk and starts hitting on the female bartender and eventually the cocktail waitresses (myself included) telling us he could get us all much better jobs in Atlanta. The girl he’s on a date with has started crying at this point and once he actually notices he yells at the bartender because it was obviously restaurant’s fault for her being upset. She yells at him to stop yelling at the bartender because he’s been such an awful date and he goes off, tells her he didn’t even want to eat here, she should’ve picked a better place, and he isn’t paying for her food and drinks. He then tells her that she didn’t look fat in her picture and he wouldn’t have asked her out if he’d known she was that big (probably met online kind of thing). She retreats to the bathroom and the guy continues to make a scene. Another girl at the bar and I go to check on her while the bartenders and manager try to deal with him. The girl is super upset and I tell her there’s a back door she can leave through and I can get her tab from the bartender. I go back out and the guy had already stormed out and refused to pay, leaving his date with a nearly $200 check. She didn’t have the money to pay so a couple of the bar regulars covered it. Made the whole night super awkward and stressful. Definitely one of the more memorable experiences of that place.

50. When I was a waitress at Olive Garden, one of my tables was going over their divorce paperwork. When I greeted the table I asked how everyone was and the woman said, “Terrible! We are getting a divorce.” Like wtf do I say to that?