Dating, particularly first dates, are commonly a bit stressful. Imagine trying to manage small talk with a stranger, all while trying to leave a good impression of yourself and evaluate your counterpart at the same time. So it’s no surprise that sometimes things just don’t go as planned.
We’ve gathered stories of awkward and unhinged date moments as shared by restaurant workers from across the internet. So get comfortable as you scroll through, upvote your favorite and if you’ve overheard or sat next to a date gone wrong, feel free to detail the story in the comments down below.
#1
I was serving a couple probably in their mid twenties. It was Valentine’s Day and they were arguing a lot (probably because it was a chicken wing place and Valentine’s Day). The guy ended up calling me over to the table to calmly ask me, in front of his date “Do you have a high chair or a booster seat since someone wants to act like a d**n child” .
I was speechless, she wasn’t. They left soon after that.
Image source: Puddin__pop, Getty Images
#2
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.
Image source: Durnovarian, Getty Images
#3
Mid twenties aged couple on a date. First date I think but I’m not sure. Seem a bit awkward but make small talk throughout dinner. When it’s time to pay the guy asks for separate checks. Girl looks surprised. He pulls out his card and pay then goes to the washroom. I run the girls card (she already looks nervous) and it gets declined. We try again, it is declined again. I ask her if she needs a moment to figure it out (check her online banking or w/e) and she says yes. Guy comes back. She runs her card again (declined) and he sits stone faced while she is getting more and more anxious. I walk away again and when I come back the guy ends up paying for it. He wasn’t thrilled. It was super awkward for all of us, but I cringed so hard when it was obvious she had just EXPECTED him to pay for her.
Image source: Theywerethereyouknow, Getty Images
#4
I bartended at this restaurant for years that for whatever reason was a hotbed for match.com/eHarmony/OurTime first dates. Our clientele was usually in their 40s and 50s and so were our first daters.
They were always entertaining, some even ending in the parking lot for some extra curriculars. However, one stands out above all else. The couple meets and they begin talking. I got a weird vibe from the woman for most of the evening but it was a busy Saturday night and I didn’t have time to pay too much attention. Hours went by and as business died down I overheard what had to be the interaction of the night.
Guy: well this is my first time doing this online thing. I think it’s going pretty well!
Woman: oh… oh god, no. No it’s not going well. You look nothing like your picture and this conversation didn’t just make up for that. I’m going to do one more so I can justify coming out here while you Settle up with the bartender.
She proceeded to order another KJ Chardonnay. Price: 9.75 a glass. Her sixth of the night. The man, who I couldn’t help but feel for, handed me his card, signed his tab with the look of absolute defeat and then proceeded to sip his beer until the woman finished and left for her Uber.
I bought him a drink, and then he left. I never saw him again. I hope he didn’t give up.
Image source: TheAmericanCharacter, Getty Images
#5
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.
Image source: anon, Antonio Verdín
#6
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.
Image source: geewhizz90, Getty Images
#7
I’ve told this one here before. 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 f*****g dessert, eventually he came back and paid and they left together. Super awkward.
Image source: Lampmonster1, Tamara Harhai
#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.
Image source: ThereandBack22, Ivan Aleksic
#9
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 f**k up with piercings to match.
The woman orders her dish and before I get the guy’s order, he says in a s**y 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 f****h for like three years.
Image source: significantmundanity
#10
I witnessed another waitress accidentally drop a *very* small (and plastic, like a plastic cup) container of coleslaw on a baby’s head, coleslaw side down. The mom was LIVID but the dad was laughing his a*s off, making the mom even more pissed off. The poor waitress had no idea what to do besides get some paper towels for them.
Image source: kiasrai, Matteo Discardi
#11
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.
Image source: HappyLittleTrees17, Dongki Koh
#12
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 b***o 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.
Image source: nmouchel
#13
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 r******d? 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.
Image source: Penya23, Abdurrahim Israfilov
#14
Late to the party but I will share my story. 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 F*****G B***H 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.
Image source: CigarJpug, Getty Images
#15
Not a waiter but I was working as a supervisor in a restaurant. And there was a drama lasted for a couple of months.
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 s*x. 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.
Image source: big_ma05, Tim Mossholder
#16
I started working at the current restaurant I’m at a little over a year and a half ago. About six months into my job, this couple comes in, probably mid-20s. Their posture is rigid and they’re not looking at each other. They actively avoid touching each other (it’s a lunch counter-type place, so people often crowd around the counter to order if they’re in pairs/groups). It takes a while for their food to come out, so they decide to sit down and have a very serious conversation (with grave expressions, whispered tones, and everything). I suddenly realize this is a breakup lunch meeting.
When I go to bring them their food, the woman is fidgeting with her phone and looking down at her lap. The man is crying. Not loudly, but his eyes are glassy and all the ice has melted in his drink. I just go “hi here’s your food” and leave as quickly as I can. The woman gets up a few minutes later and asks for a to-go box and leaves shortly thereafter. The man just sits there, staring at his food. He doesn’t touch it and eventually leaves without getting it to go.
I don’t think I’ve seen anything sadder in my life.
Image source: SolidVirginal, Alyssa Jane
#17
Had a couple come in. Guy is telling woman about some real estate investment opportunities he has coming up (for himself). She tries to tell him she doesn’t think it’s a good idea and he responds with “no one asked for your opinion, you don’t know what you’re taking about”. She sat in silence for the rest of their meal, looking at her phone. When he goes up to pay, and I go clear some of their dishes away, she tells me it’s only their second date, and she doesn’t think she’s going to see him again. Couldn’t bring myself to respond with anything other than “please don’t”.
Image source: saphs1477, Andrej Lišakov
#18
I used to work the bar at a restaurant that was walking distance from a -very- rich neighborhood. One of my regulars was an NFL player who would bring his fiancé in a couple times a month. One day the fiancé came in alone and already very drunk. She sat on her usual barstool and started rapid-fire typing on her phone without ordering anything. I kept my mouth shut, because she was already wasted and she usually tipped me very well. I turned my back to type in someone else’s order, and I heard someone yell and then the sound of breaking glass. Turns out Mr. NFL player had walked into the restaurant with another woman. The fiancé had picked up someone else’s drink and threw it at his head.
Image source: MahouHairdo, Artur Voznenko
#19
I don’t really know if this counts because I think they were married.
At a table with two crying children, “how are you doing tonight, what can I get you started with to drink?”
Father “do you have a shotgun back there so I can blow my head off?”
The wife’s glare at him was the scariest thing I’ve ever seen, I honestly hope that man is still living.
Image source: RhodeIslandisFake, Zahra Amiri
#20
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.
Image source: AgainstBelief, Ivan Samkov
#21
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 guys brother. Apparently glasses were thrown across the room and they both got kicked out.
Image source: Foxjessie, invadingkingdom
#22
I guess a husband and wife is a “date”. From the last time a similar question was asked. It’s been more like 13 or 14 years now.
> I waited tables at the Olive Garden 10 years ago. Not really f****d up as much as it was funny. A guy and his wife sat down at a table and immediately started arguing. Something about his affair and how a baby from it was costing them money. Finally it culminated as I was bringing out their salad. As I walked away I heard the wife say
>
> “Well maybe if you hadn’t boned our sons girlfriend and gotten her pregnant, we could afford to eat somewhere nicer than the f*****g Olive Garden. Oh look, the highlight of my meals, unlimited.f*****g.bagged salad. Maybe you could save up and we could go to Joe’s Crab Shack for our anniversary. A*****e.”
edit: holy c**p. This comment has always been my 2 top rated comments (now top 3) but I didn’t expect 16k. Well… Hope you enjoyed the show as much as I did at the time.
Image source: PrawojazdyVtrumpets, Matt W Newman
#23
Idk if this counts, but 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?
Image source: kiwikoopa, Curated Lifestyle
#24
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.
Image source: spoooky_spice
#25
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?
Image source: midgetT-rex
#26
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.
Image source: icysunshine
#27
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.
#28
Couple came into the restraunt 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 tasted. 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.
Image source: hexiron, Dominik Day
#29
Saw a really young couple, likely 13 or 14, come in and not say anything to each other. Neither could look each other in the eye they were so shy, and ordered their food barely above a whisper. Occasional cringe faces made at the food they were staring at. They were having a very awkward time and it was painful for them as well as me.
Image source: Gozen_777, Yunus Tuğ
#30
I am a barista and had a gay couple sit at my bar while on a date. They were super friendly and talkative and seemed to be having a great time. It was really slow and they were asking us a lot of questions. My coworkers and I had a competition to see who could make up the best drink and had them both try it and vote. They thanked us for a great time and walked to the parking lot. About fifteen minutes later, one of the guys came back in the restaurant in tears. His boyfriend had broken up with him in the parking lot!
Image source: RedPlanit, Eduardo Ramos
#31
No joke, had a woman bring in a candle and put it in on the table. Not a little candle but a big, giant one. I told the woman her and her date could NOT have that on the table and she literally said “Y’all tryna get hit?”
This was in a mall in a pretty big town at a chain restaurant. I just couldn’t believe it. Thank God managers exist.
Image source: feebleposition
#32
I had a close call with an incredibly awkward story, but it ended just fine. I had a guy come in, maybe 16 or 17 and he got there first. He order her soft drink “for the lady” (his words). Then he ordered a meal for her. I was starting to get a little worried, when several minutes went by, and he was still all alone. Was this an actual girl, or was he just imagining her. Then I delivered the food, still just him sitting there. I was feeling really bad… he was a bigger guy and wasn’t classically handsome, but he seemed really sweet every time I went by the table and I wanted so bad for him to have someone special. I was so glad when later I went by there was a sweet looking girl sitting across from him, happily chatting as she ate the meal he ordered.
Image source: StephyJo23
#33
I worked at a Subway a long time ago. My regular doctor came in with one of the medical assistants (not his wife). They were sitting side by side and she kept rubbing his leg.
Dude, you’re a doctor. Use that brain of yours. If you are going to be a d**k and cheat on your wife, at least go on dates in another town where people won’t recognize you.
Image source: anon
#34
A man looking to be in his late fifties came in wearing a nice suit, watch, tie; the whole shabang. Say him down, he said he had someone else coming. A bit later a pretty Asian woman came in. I asked her where she would like to be sat, but she gave me the “I don’t speak English look/gesture” and started looking around. She saw the guy and sat with him. He very obviously had been expecting her, I could tell by how he greeted her. Then proceeded such a one-sided conversation attempt I’d ever seen. He would keep saying things and asking her things, to which she of course couldn’t understand or respond to due to the lack of english. ‘‘Twas an interesting night.
Also they stayed 30 minutes after closing so ultimately, f**k them.
Image source: ihatehorrormovies
#35
A guy proposed to his girlfriend at the booth across from my friends and me…at Olive Garden.
When he got down on one knee and opened the box, she was shaking her head and then just stared silently. It must’ve been a whole 30 seconds of pure silence, but it felt like an eternity.
Then, the guy proceeded to describe the ring, how much it cost, the different aspects of it, etc. Finally, the girl just went, “Nooooooo” and the guy just sat back down and they tried to finish their dinner. I caught eyes with our server and he made the most perfect “holy hell that was bad” face. Geeze that was awkward.
Edit: I still picture him saying “My love for you is like these breadsticks…Unlimited
Image source: bonsai_bonanza, Mike Mozart
#36
Bartender at the time, not a waiter, but they were righ in front of the bar.
attractive woman comes in with a very loud dude who never took off his rollerblades, humblebrags badly (mostly just bragd he clearly thought sounded humble) loud enough for me to hear in a bar for about an hour, thanks her and leaves.
he thought it was a date, apparently she was doing sociological research on people who use tinder.
i was relieved.
Image source: throwawaybreaks, Good Faces Agency
#37
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.
Image source: mesoziocera
#38
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 didnt 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 didnt 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.
Image source: wheelchair_boxing
#39
Not a waitres but I was sitting close to them. The guy was on one knee and holding a small black box. When she open the box he ran away. There was a small paper inside. After reading it she started to cry. Turns out he break with her. It was funny/sad at same time.
Image source: Stepan1894
#40
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.
Image source: ANPhiK
#41
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 s*x 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.
Image source: anon
#42
Well, I’ve commented on this before, but basically he was waiting for his girlfriend and he noticed his wife’s best friend come into the restaurant. So…. that was awkward for him.
edit: Meh. He frantically texted the gf, she knew he was married, when she showed up she sat a few seats down and they talked without looking at each-other till the friend left.
Honestly it was kinda ant-climactic. He even went over and said hi to the friend.
Image source: thepizzapeople
#43
They came in and the first thing I notice is that the woman was noticably older than the man but I don’t really judge about that kind of thing and I also don’t assume people are on dates. maybe she is his aunt? or they are just friends?
So I went to go ask about drinks and do the usual peppy greeting and she is super chatty. Bascially talks for him and answers questions that were straight for him. Okay, I think, maybe that’s just how they are. whatever. She proceeds to order them both hard alcohol straight..at 10 am.. I figure “eh maybe they are on a vacation together”. You never know.
It finally hit me that something wasn’t right was when she wouldn’t stop making sexual comments about the two (which is how I knew it was kind of a date). I am talking straight up things like “I am 53 but with the amount of work I have had done to my downstairs, he won’t be able to tell tonight if I am actually 23” I am watching the mans face and he looks pained.
I watch the table from afar. I realize it kind of looks like a date gone wrong, but they seemed to know each other so I am not really sure what is going on (and servers always chat and theorize about their customers in their free-time) when the man gets up and comes over to me and asks me to chat with him around the corner really discretely. So I do. He looks as me and is talking super fast as he explains that this is his boss and he has to meet with her quarterly and she just has to sign a single form to approve what he has been doing and she insists on going out for a meal and drinking and then trying to sleep with him. Every time. I was horrified for him– he looked that panicked. He said that he usually gets her to sign it before they leave the restaurant and then makes an excuse to ditch her. We made a code sign (him patting the back of his head three times) so that I could intervene when she would get far too inappropriate but honestly she didn’t change much when I would come. He also asked me to bring him fake alcoholic beverages, said I could charge him for the alcohol but to make them water or just soda.
I still think about him sometimes and wish I had gotten his name or something so I could check in and encourage him to report her, but in all honesty she probably owned the comany he worked for or something the way she spent money and looked like.
Image source: rufusmaru
#44
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.”.
Image source: youngandstarving
#45
We had an older lady come in on a Saturday morning. She happily informed the server that she was waiting for a date, and ordered a mimosa to drink. About three mimosas and forty-five minutes later, we start to think maybe her date is a no show. The waitress sits down and starts talking with the lady, trying to assess the situation, see if she still wants to order and what not.
That’s when it gets strange. The lady says that her date was going to pay for the meal so she didn’t have any money, and she wanted a fourth mimosa. Meanwhile she’s cheerily looking out the window for her date, obviously nervous / excited to meet him, and very talkative. The server asks the manager what to do, so he sits down at the booth with the lady to talk with her.
Turns out, her date was Lynyrd Skynyrd and she had dementia :(
Image source: _EAT_BERTHAS_MUSSELS
#46
I’ve worked in several restaurants over the past 25 years. The awkward dates, at least in my experience, are always the ones where the girl (girls in these instances = 16-25) is pretending that she doesn’t eat, usually first dates. At Burger King, in high school, she orders an order of fries and either gets water or a diet drink. When I worked for Pizza Hut, girls would always order the salad bar, and “Maybe I’ll have a slice when it comes”. A chicken wing joint I worked for: a side salad.
The guy would always stare at the girl like she’s lost her mind.
Image source: anon
#47
Another story! This is the tale of how I accidentally become someone’s closet hanger.
So about a year into my current job, a young woman about my age starts coming in with one of her (also female) friends. She’s very beautiful–blonde, fantastic body, extremely sweet and bubbly. The second or third time they come in, they’re dressed to the nines–girls’ night out! They order a round of very strong drinks a few times and they chat me up a while. I guess also being a young woman, I’m disarming? Idk I try to be social but I’m awkward as hell.
After a while, they get drunk–and the blonde girl starts laying it on me thick. I’m kind of lost, I get flirted with somewhat regularly (alcohol + food + relaxed people = s*x? idk), but I’ve never been flirted with by another woman. They leave eventually and the blonde girl departs with a blown kiss and a wink. I’ve never been so flustered and bisexual in my life.
She comes in every so often after that, progressively more sober and progressively more flirtatious. She’s touching my arm, batting her lashes, the whole nines. My male coworkers (at the time, I was the only woman working there) are insanely absorbed in this and constantly ask me for updates. She keeps flirting and I keep not knowing what to do except weakly go “oh yeah hahaha I’ve got a boyfriend.” She’s never deterred.
But then! It happens!
She comes in a few months after this all started–WITH A GUY. And she does not look happy. I was working a shift that I usually didn’t cover on an odd day, so she was shocked and visibly displeased when I waited on them. The guy with her is totally oblivious and a very chipper dude. I introduce myself, say “oh yeah (woman’s name) is one of our regulars!” The guy goes “oh yeah, my financee never stops talking about this place! I totally thought we should come!”
Oh no. I put all the pieces together– I’m her gay crush, but she’s engaged to a man. I have never seen a human being redder in my life as she was. I quickly take my leave to get their food. Throughout the night, he gets up to leave to go to the bathroom/order more drinks/whatever, she’s adjusting her hair and touching up her lipstick. It’s a disaster. I’m dying inside.
They come in a couple more times, until she suddenly announces (without looking at me) that she’s been accepted to medical school, so they’re moving. And I’ve never seen her since.
Image source: SolidVirginal
#48
Well I’ve had exs show up to the bar I worked at with their new squeeze. Usually ended with them being sloppy drunk hanging all over the new guy, and me being super happy I didn’t have to deal with it.
Image source: cbyrd
#49
I worked at a Chilibee’s type restaurant. And a woman proposed. At f*****g Chilibee’s!!! Like on her knee on the dirty floor in front of a full house and their kids. F*****g Chilibee’s!!!
He said yes. But it was still the most awkward I’ve ever felt with a table.
Image source: sarcastic_patriot
#50
This man and a woman came in and it was obvious they were a newer couple. She started to order fries, but he interrupted and said she didn’t need the fries and she should have a salad instead. She was super embarrassed because the way he said it he was clearly body shaming her. Pretty sure that was their last date (I hope at least for her sake!).
Image source: makeitwork1989
#51
Oh my god. Not a server currently, I was sitting at a brew pub enjoying a very delicious crafty beer in the corner booth, writing some silly jokes for stand up That night. I am always aware of my surroundings and find myself looking up or over whenever someone new comes in. I briefly looked up and saw the hostess talking to a man and not taking him to a table. Whatever. I go back to writing. A minute passed and this man takes a seat at my table and says “Amber?”, I look up at him VERY confused. He repeats, “Amber? Fet Life?”… I lost my composure, laughed through my no. Just f*****g what a ballsy movie. He got up very embarrassed and thats when the girl at the booth next to me very sheepishly said “I’m Amber”. I hope to god the hostess saw that exchange.
Image source: DarthBeiber
#52
This woman arrived before her date and was sitting alone in the booth waiting. She had a kind of generally angry air about her. This woman was enormous, and the hostess had seated her at one of our smallest booths. Her stomach was fighting the edge of the table.
She ordered a glass of wine and sat there drinking it. By the time the guy arrived she had finished it. I asked her if she’d like another glass, and she said with a scowl on her face, “I don’t know. It depends on whether or not he’s paying.” The guy looked kind of embarrassed and said sheepishly, “Uh, yeah I’m paying…”
I wanted to tell him to run far away.
Image source: anon
#53
I was waiting on a table around 3pm on a weekday, so they were pretty much the only people in the restaurant.
The woman had just revealed she was pregnant. The man was not thrilled, to say the least. They decided it was a good time to hotly debate getting an abortion.
I also waited on a married couple who I knew loosely because they were regulars and casual friends of the owners. One of them decided it was the appropriate time to ask for a divorce.
Image source: BreakfastInSicily
#54
A few years ago I was working and a bar and we had this regular, and when I say regular I mean he used to come in 3 or 4 times a day.
Every time he came in he had a different girl with him. EVERY. TIME. Not once did I see him with the same women in the year that I worked there.
Tinder is a dangerous thing people.
Image source: PurpleZebra94
#55
Oh god, I feel bad just remembering this.
A couple were seated in a booth all lovey davey. They shared a dish of whatever. A bit after I look over and they are gone. I walked to their table and I notice he forgot his coat and on the table there is a note that read: I had a really good time but I have to go, I’m sorry!
Didn’t understand at first but 5 seconds later the dude walks out of the washroom. I’m standing there note in left hand, his jacket in my right hand and fully understanding that she ditched the dude as he went for a wiz. I look at him and said “I’m sorry man.” His face changed instantly. I should have given him a hug. As he left he still wished me a good day.
She was all smiles before so I dont get it.
Image source: cmach86
#56
I work at iHop, and I genuinely enjoy it. I used to work graveyard shift though (my shift being 11pm-7am), which meant I came across a lot of interesting people. I have SO many stories I could tell, but one of the most awkward/uncomfortable situations for both me and other people in my restaurant was when this guy starts shooting heroine in a booth. I had to go tell my manager who didn’t believe me at first.
Another time was when a guy came in around 2am with the restaurant totally empty except for me. He was shirtless, bleeding, out of it (but didn’t seem under the influence of anything), and wanted to use our phone.
Image source: Braangster
#57
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 f****d up even a McDonald’s date. Guess he ordered the wrong thing.
Image source: shadez36
#58
Bartending a day shift at an upscale Italian place in a high-end shopping centre over the Christmas season. Couple comes in, starts drinking and is VERY flirty with each other. They clearly liked the attention. I wasn’t quite sure why the man seemed familiar but he had a face I knew from somewhere.
Midway through their lunch the woman used his name and it dawned on me that the man was the husband of my previous boss. I told him he looked familiar and asked if he was “Mark” from “That Restaurant on the way to the Beach?”
He said that he was not but the woman he was with insistent on making it awkward and peppered me with questions like, “I’ve heard the owner of that place is crazy, did you know her?” She was backhandedly trashtalking “Mark’s” wife and the whole thing was so uncomfortable. He was an all-around bad dude though and deserved it.
For additional context, his family had owned “That Restaurant on the way to the Beach” and his wife (my former boss) ran the place until she caught him cheating. They divorced, she got the restaurant and continued to run it with her sister.
Fast forward a few years and the two eventually remarry. It was during their second marriage that he turned up at my bar with his mistress.
Image source: ryan_peay
#59
This wasn’t so much as awkward but just unusual: 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.
Image source: Oreosforever
#60
My ex gf with my friend. He didn’t know I worked there but she did.
Edit: sorry, because a few people asked. We were dating at the time. I was young (15) and she as well (16). I think she wanted to break up with me, didn’t know how to do it, so did it this. It was hurtful (and obviously I was very sad and angry at the time), but I don’t hold any ill will towards her today. I think maturing is a tough path. My friend at the time knew we had been dating, but he was the sort of friend I see twice a week in class, and apparently she told him we had broken up… I dunno – kids do silly things.
Image source: Wittyandpithy
#61
The couple started shouting and then both went into the washroom… we thought they were smashing and dashing without paying, but they came back. I heard some of their convo and it was sooooo awkward. Guy: “so do you golf cuz I golf?” Girl:”No.” And it went on like that for their whole date.
Image source: PM_MOI_URBIGTITS
#62
So I’m not 100 percent certain, but one time I think someone went to the chain I worked at to meet their mail order brides (it could have been prostitutes, looking back on it, but I thought this at the time). It was two guys in suits that came in seeming really nervous.
One comes up to me and lets me know what the girl looks like in case she’s confused when she comes in. I’d never gotten a heads up like this before and he seemed super nervous/ sketched out.
So, the women come in and they don’t speak very good English and have heavy accents, which stood out in the small neighborhood. They were dressed very minimally for it being cold and raining outside. I point them out to the table with the two men and they’re introducing themselves like it’s the first time they met with awkward hugs and asking about their flights. I got to overhear some of the stilted conversation and talk of money while passing by.
The other time was when an ex of mine came in with his girlfriend and she left crying for some reason halfway through. Apparently he brought up that we dated and he kept looking at me, which somehow caused that whole scene.
Image source: Rangerstation01
#63
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.
Image source: anon
#64
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 everytime she’d look me in the eyes following.
Image source: PrinceLemonade
#65
Eastern European couple walks in. She looked like she had been crying, but they ordered and seemed nice enough. A few minutes later, I heard a commotion going on in my section. I got there in time to see this man reach over and slap the woman hard enough that the whole lounge heard the sound. He looked like he was gearing up to hit her again, so I instinctively stepped in (I was and am a small, petite woman with no martial arts training or anything) and told him to back off and leave or the cops would be waking him out. Surprisingly, he just left without a fight. What was disturbing is that the woman very quickly composed herself and by the time I went over to check on her (seconds later) she was brushing it off like it was an everyday event. I guess it was for her.
I told her I would feel better if she stayed in the lounge for a bit, so we could be sure the man was gone. She agreed and I got her a few drinks on the house. Once she was a little more opened up from the drinks, she told me her story, about how this man brought her to the US and that she was afraid if she left him, she would end up being forced to go back home. She also warned me never to date an Eastern European man and that most of them were like that. I wanted to take her to the police or to a women’s shelter, but she refused and wandered out into the night. I never saw her again, but I hope she is okay and away from that man.
Image source: PsychologicalCoat71
#66
Husband and wife fight. Wife cried. Husband got up and threw a pizza slice at her face.
Image source: Agentx6021
#67
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.
Image source: Corticulture
#68
Am a bartender and seen a bad date go down. The girl seemed familiar to me and she kept glancing over at me every now and again, then the guy started looking over at me too. Even when she was up ordering drinks she was glancing at me and my co-worker noticed. Turned out she was a friend from years ago who just ghosted our friend group.
The couple had no chemistry at all either, there was little conversation and at a few points both were on their phones at the same time. Eventually the guy leaves and the girl’s left there alone for twenty minutes so she pulls out her laptop and works on Photoshop for a good half hour before leaving.
Image source: Cyanide_Revolver
#69
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.
Image source: kklolzzz
#70
Chiming in late, but one comes to mind.
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 c**t” 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.
Image source: LSDnoiseparty
#71
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 f*****g 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.
Image source: Darnrightimupset
#72
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.
Image source: CMMND
#73
I am not a waiter but a bartender, but this particular moment is something I never forget.
My shift began at 7pm and when I arrived at the bar at 6, my manager told me there’s a guy who wanted to propose to his girlfriend at this bar and he wanted me to help him with it. I said ‘Sweet, no probs.’ so the manager gave me a ring and told me to put it on top of her drink.
Fast forward to the date, the girl was wearing normal thing you would see at the bar, low cut top, black skirt and heels and s**t. The bar was pretty busy. She ordered a Long Island (f**k you Laura), so I put the ring on the straw and hand it to him. She had the ‘What the f**k mate?’ look and then he dropped on his knees. Our manager put on some romantic songs. To my surprise she threw the drink at the poor bloke and ran out of the bar.
Later I came to know that it was their second date.
Image source: Yo-effing-lo
#74
I just clocked in and my first table is a young guy waiting for his date. He says he’s meeting her for the first time and didn’t want to be late. What a sweetheart. I come back to the table after 5 minutes and see a girl sitting across from him, her back facing me. I notice she has a slim figure and nice long black hair, and from the back she looked like a beautiful woman.
I walk up to the table and start to get their drink order. As I look up at her, I notice a 5 o’clock shadow above the upper lip that had a lot of foundation over it and a very apparent Adam’s apple. She was definitely a he. I could already tell he was uncomfortable with the situation, and wasn’t hiding it either. But, they stayed for a beer and finally parted ways. He left me a little note on the receipt after paying. It said “I think my tinder date is a dude.”
I also get a lot of crying girls that are mad at their boyfriend. That always makes things awkward.
Image source: anon
#75
Server here! Following a power failure, my date was reset making my SSL certificate invalid. Very awkward for anyone trying to visit the Applebee’s website, I tell ya.
Image source: brandonsh
#76
Semi-related story time: So I used to be a cook, and worked at a bunch of different restaurants in a relatively small town. And, as most cooks do, I spent a lot of time drinking and meeting/hooking up with servers. So one night I was going out to eat with my family for Father’s Day. Traffic was a b***h, and I was running late, they ended up getting a table and ordering drinks before I got there. I walk up just as my dad is finishing his first beer. As soon as I sit down and start looking at the menu, I notice the server walk up out of the corner of my eye. I start to turn around like “hey can I get uhhhhh oh. Hey…” Yeah it was a girl I hadn’t called. So that was great, and of course then I had to explain to my family how I knew her.
I actually liked her too, but I was more concerned with doing other things at that part of my life. Mainly d***s. A*******n is a b***h.
Image source: anon
#77
A lot of the time, dates seem to be going well until it’s time to decide whose paying/how. Yiiiikes.
Image source: antisocialite-
#78
I’ll answer this one for the server, my sister was single and the server was attractive. So my mother’s train of thought was “in going to hookup my daughter and this server”. Cue 40 mins of me trying not to be noticed as my mother asks him if he’s single, looking to date, showing him pictures of my sister. What’s even worse is we came back another time, coincidentally with my sister, and my mother introduced her to him after we got him as a server AGAIN. My mother isn’t a crazy person but this was cringe off the charts.
Image source: nateshat
#79
They were literally so silent and uncomfortable. every time i came over the guy was talking to me like he was trying to impress her or something. i felt so uncomfortable for them. there was only so much ice breaking i could do. i felt involved for some reason.
Image source: loveadumb
#80
Work in a cafe later in the arvo a young couple came in, maybe 17-18 and went in the very end booth. Wasnt two minutes later and the whole cafe was filled with the sounds of sloppy kissing. Felt sorta bad for them since i assume they thought they were so subtle, meanwhile the whole cafe customers and staff were listening in, wasnt a optimal situation.
Image source: anon
#81
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 f*****g d*****s 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 f*****g 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 s**g on the first date.
Image source: troyantipastomisto
#82
There was a couple at a table next to me at a bar. I was having a good time with my friends and I was singing something as I usually do (just like that, not loud or something). The guy heard me and said:
Guy: This one is for my ex gf!
Me: Yeah, that b***h!(As a joke)
The girl turns around and starts too yell at me. Turns out they were just breaking up.
Edit: I forgot to say she was crying but I couldn’t see it at first because she was facing the other way.
Image source: mukiuki
#83
My first table ever at a job I started in 2012 was a break up, and they were one of two couples in the restaurant. It was at 5:20 pm.
Image source: SuperSalad_OrElse
#84
I used to be a server at Applebee’s. Y’know, the most classiest restaurant chain in the country… I was serving what seemed like a normal family, a dad, mom, and their daughter. Halfway into the meal, I’m near the bar and the dad comes up to me and asks where the bathrooms are, I kindly show him, then he hands me a ring, and says he’s proposing tonight. He asked if I could put it on the plate with their microwaved chocolate cake dessert and bring it out to the table. I stopped for minute, and almost told the guy to rethink his proposal environment, but ate my words and kindly went a long with it.
I go to the back, and dress that dessert up so much it looked like it came out of TGIFridays. Delivered the dessert to the people I thought were just out on a family dinner but were actually out on a date with someones kid tagging along. Put the plate on the table, smiled, and ran away cringing. I then check back a couple minutes later, the table is dead silent. They’re just enjoying their desert, no excited emotions, or anything. Very normal.
Eventually drop off the check, they pay and go on their way like they came in. Go to pick up the credit card slip, the guy leaves a note saying ‘She said yes thank you’ and leaves me a 100% tip. I was pretty shocked, but happy for the dude.
I really just hope the restaurant had some kind of sentimental value to them, then I’d understand.
Image source: dazedfinch
#85
I’m not a waitress, but I was at a restaurant waiting for a friend, and I overheard the most awkward date ever.
It was a pretty nerdy looking white guy and a Chinese girl who didn’t seem to speak much English.
First, the guy would literally not stop talking about his mother. Everything the girl tried to say, he’d be like “Oh, that reminds me of this thing my mom said.” Or “Oh the shirt you’re wearing reminds of this shirt my mom has.”
Then, he started quizzing her on complicated English SAT words like “fecund.” And sounding really smug and condescending when she didn’t know what they meant and he did (since English was clearly her second language).
The best part was when she asked him if he knew what “hegemony” meant and he didn’t. She explained it to him, nice and smiling, but obviously proud, which as a non-native speaker, she should be, since most native speakers probably don’t know what that means.
Instead of acting like a normal person and being impressed, he was super b******t and was like “Well, that’s not a word anyone in America uses anyway.” As if people regularly use the word fecund. It may not be common, but I’ve at least seen the word hegemony outside of SAT/GRE prep class.
Then, he tried to speak Chinese to her. I’m not a Chinese expert, but my college roommate was Chinese-American and we watched enough dramas in Mandarin that I could tell this guy had no idea what he was doing.
The girl kept smiling awkwardly and being like, “Oh, did you mean this?” And, no he didn’t mean that, and he was super irritated that she wasn’t getting it. He kept saying, “Well, I learned a particular dialect, so I can see that maybe *you* wouldn’t get it.”
I just wanted to slap him and say “THIS IS PROBABLY THE PRETTIEST GIRL WHO WILL EVER DATE YOU, WHY ARE YOU F*****G THIS UP SO BADLY?!!”
I didn’t hear the end of the date, fortunately, because my friend came and I couldn’t eavesdrop as blatantly. But she did get up and leave less than 30 minutes after getting there, so I don’t think she was very impressed.
**TL;DR:** White guy with pretty Chinese girl. Talks about his mom constantly, lectures her about her (very good) English-speaking skills, speaks terrible Chinese to her and gets mad when she doesn’t understand him.
Image source: trexrocks
#86
I once witnessed a blind date when I worked at a French restaurant that started like this:
Man: /already seated
Woman: /arrives, takes a seat
Me: /introduces self, asks what they would like
Man: let’s start with a carafe of red, *avec* bread. ::he turns to the woman:: that means *with* bread.
Woman kinda gave this look like, “Oh. God. Dammit.”.
Image source: cheatatjoes
#87
– a couple that frequented our restaurant had recently divorced.. hubby comes in with new girl while ex wife is dining with friends, well within eyesight. she kept asking me to get details for her and it was just messy.
– guy broke up with girlfriend while they were eating their appetizer. They stayed for entrees and dessert. He ate, she cried.
Image source: openfloor
#88
I used to have this family of regulars that came in for dinner; it was a man and a woman in their mid-late thirties, and two girls, maybe 8 and ten-ish. When they got there, one of the girls would say ‘Dad, can we go pick out our table?’ and they’d try to get this corner booth every time. He was a pretty cool guy, but I didn’t really talk to the woman very often.
Anyway, they came in for dinner one time and I noticed it was just them. “No kids tonight?” I asked him. He gave me this surprised look and doesn’t reply. Ooookay then. So I went “You folks want the usual spot?” Still no reply, just a couple of odd looks. I sat them at a random table nearby and handed them their menus. She looked a little different, so I asked her if she did something new with her hair. The guy just starts getting pissed off and tells me to get them some waters and leave them alone. Well s**t. I looked again to make sure it was the right guy. Looked like him, and I definitely recognize the red mini-van he pulled up in. So what the f**k was his problem?
Then it dawned on me; he was with another woman. Probably his sister or something, you know? But the ladies looked similar enough, and I barely talk to her anyway, so I hadn’t noticed. Well I felt pretty sheepish when I came back with their waters. Got to their table… they’re super cozy with each other, and he’s whispering into her ear. He gives her a nice kiss on the jaw when he sees me approach, and just stares f*****g daggers at me. S**t, I don’t know what’s up but it’s none of my business. I kept quiet and took their order.
I went to the server station across the room to ring in their order. He appears like f*****g magic a few moments later. Scared the s**t out of me. He still looks pissed. I tried to apologize but he cuts me off.
“Don’t you say a f*****g word to my wife if you want to keep your job,” he says Oh. Ok. I gave their table to another server and told her about my problem. We didn’t see those people again.
TL;DR Who takes a mistress to the restaurant that’ll recognize him, since he’s there so often with his family?
Edit: I don’t think there’s a way I could have told the wife; I only remembered their first names, and he paid with cash in his last visit, so I couldn’t snoop on the last name. If I tried to look these people up, I would have been in some trouble. It was 8 years ago or so.
It’s also a very casual bar where we’re encouraged to talk to customers and remember regulars.
Also I’m female, which doesn’t matter, but everyone on Reddit is assumed to be a guy ^for ^some ^^reason.
Image source: 0w1
#89
One night, a couple years ago, we had a young couple (maybe 15/16) who were on a date. It was cute, they were awkward and I guess they hadn’t been on many dates before. Then, I noticed that they kept talking to the two women at the table behind them every once in a while. It turned out that those were their moms. They were on a date, but I guess we’re not allowed to go without supervision. I get it, but in a well lit public restaraunt? And the moms had to sit right next to them? What did they think was gonna happen? I would have been so embarrassed at that age.
Image source: Longlittledoggy
#90
Ex-bartender here. I’m not sure that this qualifies as a date ,but it was definitely awkward.It was a slow afternoon shift. Older, balding, slob of a guy comes in. Younger, mildly attractive woman shows within 10 minutes or so.They order drinks. They don’t seem particularly interested in talking with me(you get to where you can read these things) so I leave them be. Like I said, it was a slow afternoon so I busy myself doing odd stuff around the bar. While doing this I pretty much hear everything they said. Turns out he is a bail bondsman. Her husband/boyfriend was in jail and she didn’t have the money to post bail. He basically offered to cover it if she slept with him. She was crying her eyes out. After 15 minutes or so of pleading/crying she finally got up and left. The s*****g finished his drink and left. I wanted to vomit.
Image source: devolutionary23
#91
Used to work at a private, members only country club. There were lots of ladies who came in to eat lunch and play cards, groups of men who played poker and smoked cigars in a different area, a main dining room, etc. A woman who was playing bridge with her red hat society went balls-to-the-wall crazy one day.
Gentleman comes in with a woman, very nicely dressed. (This being the normal attire, but they were to the extreme.) I bring water, our cheese and cracker board, day menus etc. He sits down with her, they order, and I take out their food and glasses of wine. When she goes to the restroom, he tells me he’d like me to wrap this tennis bracelet around her next glass of wine. My manager and I get it looking spiffy on a glass, and I start to take it to her. I walk by the bridge room. Big mistake.
Red Hat lady is following me but I don’t yet realize it. I’m two steps from their table when she snatches the glass from my tray. “You pilfering maggot!” and dumps the red wine on him, removes the bracelet, clasps it on her own wrist, slaps him in the head, and stalks out of the dining room. Everyone is wide eyed and silent. I rush to get soda water and napkins for him, and as I’m coming back, the woman is getting up to leave. She’s crying with streaks of mascara running down her face, and takes off down the hall holding her shoes. He shouts his member number to me and books it out after her.
We found out later that the bracelet belonged to Red Hat and she was his ex mother in law. First wife had passed away and he was giving his new date her old jewelry, and Red Hat recognized the bracelet.
Image source: berthejew
#92
A young couple were enjoying themselves. Seems like the dude was pretty cool and straight forward and she seemed to enjoy his sense of humor.
But then the food came.
Young man kept talking with his mouth full, chewing loudly. Spitting food out onto the table unintentionally but noticeably. Wiping his hands on his clothes.
She looked grossed out. She stopped eating told him she had to use the rest room. Never came back.
After a half hour he got the hint and asked for the check.
I really felt sorry for the kid because he didn’t realize what he did wrong.
My manager owed me a favor so I asked him to cover the check.
Told the dude it was on me and let him leave.
Image source: pockets1989
#93
Not technically a date, but a wedding in the Taco Bell lobby at lunch time.
I was the General Manager, they both worked for me. They had picked up their checks that morning and mentioned to another team member that they were getting their marriage license that day, but had not made any other arrangements yet. That third team member informed them that she was ordained as something or other and could officiate for them. They decided to go cash checks and come back to do the deal in the lobby… No, it did not last. .
Image source: roundearther
#94
I had two men sat near each other at two separate tables, both waking for their dates. I fill water glasses and let them know I’ll check in with them when their dates show up.
Time passes. And passes. And both men start looking around and checking their phones.
About 20 minutes later I check in and ask either of them if they’d like a beer.
I bring out the drinks and on my next round the men are sitting in silence together at the same table for the rest of their stay.
Kinda sad but at least they both had a drinking buddy?
Image source: moriahisaginger
#95
A couple of weeks ago, I saw a guy at someone else’s table who I thought was my friend K’s long-term boyfriend, B. I looked closer and it was, but it wasn’t K he was with. He was with another girl. I hadn’t talked to K in a while but I thought they were still together.
I went up to say hello to B and sheepishly ask about K, to see what he said. He told me they weren’t together anymore and he said it with no qualms at all. I was hesitant to believe him because I knew he’d done some shady s**t in the past, but I said goodbye to them and left the table.
For the record, he and this other girl were 100% on a date. When I asked if he was still with K, he said no and that that would be awkward for “her,” gesturing to his date. He and his date also had a lot to drink that night… ~100$ in drinks and food for the two of them in a not-very-expensive restaurant. She had six glasses of wine, I think.
Anyways, a couple of days later I saw K post a picture of her and B on Instagram, saying how much she loves him, can’t wait to marry him, etc.
They must’ve had a real awkward talk after I told her what happened.
Image source: DanifC
#96
This was a few years ago. I was out celebrating Canada Day with my boyfriend and his friend from out of town. We met up with this girl who lost her friends and I offered to let her just hang with us. Turns out she didn’t live too far from my boyfriends place, so she went back with us and had some drinks. Started really getting into my boyfriend’s friend, they were making out a lot and then he offered to walk her home, and never came back for the night.
Fast forward a week and I see her at the restaurant I worked at. She was in my section so I walked over and said hi and then noticed she was with some guy. She looked surprised to see me, but didn’t say anything. So he asks how I know her and I just say “Oh we met on Canada Day” not really knowing it was an issue. She then starts to look really nervous. He then says “I thought you were f*****g sick on Canada Day.” So I leave to get drinks and when I come back he starts asking me where I met her on Canada Day etc… and I’m just like “I have to work, so I’ll just be taking orders today.” and then he starts asking her “Why did you lie? Where were you? Why didn’t you answer my calls?” She just sat there not really sure what to say looking like she as about to cry.
Turns out the guy was her very serious boyfriend. I want to feel bad, but that girl made her bed and then f****d my friend in it… We don’t talk anymore.
Image source: anon
#97
It was actually a post-separation pre-date between my boss and his estranged wife. She met him there and they had some coffee while he finished up some stuff. It started casual and civil and escalated to her screaming at him for hiring attractive servers and questioning his motives. The actual date was…rescheduled after her fight. I say her fight because he just sat there calmly trying to reason with her.
They got married very young and had 2 kids before 19 and basically she had issues with her body that made her assume he was always cheating when he wasn’t. We all tried, but as attractive and charming as he was very serious about saving his marriage. One b**b job and tummy tuck later (that he paid for) they reconciled only to divorce 4 years later when she left him for the guy she had been cheating with for years.
He joked afterward that he should’ve had they divorce lawyer ask for visitation rights to the implants. I said he should’ve asked for one back. 50/50 split, is fair right?
Image source: CTRickycallsmeJamie
#98
I don’t know if this counts at all, but it was in a restaurant and DID involve a waitress..anyways I was a chef and recently had become single. About 25 at this time. A waitress I worked with (lovely 40ish lady) was making it her mission to find me a date as she thought I deserved a girlfriend.
So this family comes in and there was this classy as f**k girl with them, long dress, awesome hair and makeup, maybe 21ish? from what I saw, and I ask the waitress “who is THAT!?” and she replies “Oh that’s so-and-so, i’ve known her about 6 months. I’ll put in a good word ;p.” (it was a small town) So I get on with things and after the last order goes out, I do my usual ‘see how everyone is doing’ rounds and I pay particular attention to her table. I strike up a bit of a conversation and she’s lovely, smart, laughs at my jokes, even has a few of her own. Her family seems nice. I leave at just the right time. I go back to start cleaning up and the waitress is like “YEA! I saw that!” and I say, alright, see if she has a boyfriend or do whatever it is you do…
So the waitress comes back a few minutes later with a funny look on her face….and politely informs me that the girl apparently, is 14 years old. She fooled both of us! I can only imagine what her parents were thinking while I was chatting her up. But they did seem nice.
Image source: sumthin213
#99
The weirdest would have to have been this 60 year old dude with what looked like a 16 year old Thai girl. She might have been of age but d**n it looked like he found her before puberty did. She didn’t speak English so he was trying to teach her random words on the menu. Then when the waitress came to take their order, he ran away and hid around the corner so she would have to order herself. She just pointed at 3 drinks and a wrap, all while he watched her from the doorway. He then came back an gave her a standing ovation for pointing 4 times at a menu. The poor girl looked so embarrassed. He was just fascinated with her, touching her constantly and watching her eat with unblinked eyes. i felt like coming over and spraying some water in them to keep them from drying up and falling out with his teeth.
Or then there are the dudes that are hoping alcohol will make up for their lack of personality and are speed ordering drinks for the girls, hoping to get a lay out of it. The worst is when the girls isn’t drunk enough or hasn’t decided whether she’ll f**k him and they are just sitting there on their last wine after everyone has left. Seal the deal man so everyone can go home. Use all your best lines, she ain’t calling you back anyway.
Image source: ohshitword
#100
I work at a fairly upscale Italian restaurant, easily the classiest restaurant in the neighborhood. Here are a few stories:
* Two people in their early 30s walk in. The woman has made a noticeable effort to dress, sound, and look like Kim Kardashian. She is attractive and impeccably dressed/ made up. Her date is obviously sweating, wearing gym clothes and tennis shoes with slicked-back hair. We do table service for wines, so she tries about four different bottles and sends them back. She knows absolutely nothing about wine and ignores all my / the bar’s suggestions. Finally settles on a sugar-sweet bottle of Moscato. Her date is extremely annoyed and visibly uncomfortable, but she clearly doesn’t realize this. She sends back her food twice as well, though the dishes are prepared impeccably. When she gets up to go to the bathroom, her date slips me a fifty, and apologizes. They spend the rest of the evening on their phones rather than talking to one another.
* One obnoxious repeat customer came in pretending to have a speech impediment, which magically vanished as soon as he wanted to order (he laughed, and said we fell for it). He bought enough food for two meals, as well as two glasses of wine, insisting one was for his date. Granted, this was fifteen minutes before closing, and the kitchen had closed, so no one really believed him. However, he usually spent a ton of money, so we fired everything back up, and cooked his meal. It was a full 90 minutes before his date showed up. Everyone was praying he would be stood up. She was clearly uncomfortable that the restaurant was closed, he pointedly acted oblivious. She visibly cringed when he ordered her food be warmed up (though again, our oven and all of our things were off, not to temperature.) They didn’t leave until after midnight. We close at 11pm.
* We have a patio. Two young teenagers, obviously on a date, brought meals from FiveGuys down the street and ate them on our patio, completely ignoring our manager’s repeated efforts to get them to leave.
I have more stories from when I worked at a terrible Chinese restaurant, let me know if you’d like to hear them.
Image source: peaceatrebor
#101
Okay so we have these people that come to town all over the US to do roads, clean chicken farms, wiring, ect. So this one guy becomes OBSESSED with one of our bussers. At first we think oh cute. But then he finds her on Facebook, gets her number and texts her 1744748 times. He tells her how she is an angel sent from above and how beautiful she is. And she’s just freaked out.
She finds out he has a girlfriend. And tells him to f**k off and leave her alone or else she’s going to tell her. So he just comes into our place of employment and stares at her all the time.
Well one day he comes in with the said girlfriend. And she is all puppy dog in love with him. And I was stuck serving them. The entire time the guy was ridiculously awkward. And kept looking like I was going to tell her. 1/10 would not reccomend.
Image source: Werelowongas
#102
I worked at a place famous for their cheesecake, and I remember right around Christmas a little old lady coming in dressed to the nines, happier than I’ve ever seen anyone. I was only hosting at the time, so it wasn’t my table, but she told us she had a blind date and she was so so excited. Kept asking us girls if she looked ok, nervously talking to us, looking around expectantly. A half hour passes, an hour passes…. And you just see her deflate. She was stood up on her date and it was just heartbreaking. My friend begged our manager to cut him so he could to sit and have dinner with her, but it was busy so they couldn’t do that. They did comp her bill and gave her some cheesecake for free, and when she left she was still just as sweet, but I don’t know if I’ve ever seen someone look so dejected. It was really really sad.
Image source: teramu
#103
Awkward for us not him.
Veteran server in New Orleans here. About 3 years ago I was working at a nice restaurant in the French Quarter it was Mardi Gras and I’m used to seeing some unusual s**t but not at “nicer” places. Anyway I’m going back to the table after delivering food and the girl is blowing the guy right then and there. She’s not even hiding under the tablecloth like in the movies.
Bonus: This restaurant has floor to ceiling windows facing the street. I wasn’t the only one who got to see all this.
Image source: rustyjohnson504
#104
Former server, current bartender. I’ve seen a lot of awkward dates. Usually just a couple not clicking and sitting in silence, or someone not looking like their profile picture.
The worst one was when I had a date get broken up by about ten cops rushing the table. Turns out the guy was a big time d**g dealer who the cops had been looking for for quite some time. He got tackled, cuffed and taken outside. Meanwhile I’m standing there holding their food and a tray of drinks. All I could think of to say was “Sooooo.. Should I box this stuff up for you?”
One of the cops came back in to apologize, and told me they caught him because the girl had tagged herself with him at the restaurant on Facebook. So, I guess always ask your date if they have any warrants out for their arrest before you tag them anywhere.
Also I’ve seen a lot of dates turn really awkward really fast because of someone drinking too much.
I once had a guy who came in already completely s**t faced. He stood up to greet his date, tripped over a bar stool, and face planted. What made it worse was that he just laid on the floor without moving or saying anything until she left. Thankfully it only took her about 2 minutes to nope the f**k out. He didn’t get seriously hurt, just a small cut on his nose, but it was painful to watch.
Image source: anon
#105
I worked at a Japanese/Korean sushi restaurant for a while, and this will always be the most awkward date I’ve ever seen.
It’s around 6pm and a reasonably overweight gentleman walks in and sits himself down in a booth. I stroll on over, set down two menus because I correctly assume he’s meeting someone here, and ask him if he’d like something to drink other than water.
Now right off the bat he asks for a bourbon, and of course we comply and bring him one and all that. He downs it in under a minute and requests a second, third, and a fourth. I was bringing him his fifth when his date walked in.
She was pretty, blonde, heavily endowed in the breasticles, hair pulled up tightly into a ponytail and smokey eyes. Blonde looks around for a moment, and Mr. Reasonably Sloshed bounces in his seat and waves her over excitedly. Blonde looks surprised, horridly so, but walks over and confirms who he is before taking a seat across from him in the booth. He’s slightly sloppy at this point, cheeks flushed and sweating like a pig. I’m talking very noticeable b**b and underarm sweat right now, we all think the poor guy is nervous out of his mind.
“You look different from your profile picture.”
Oooh online dating, first date, and she looks absolutely blindsided.
“I hired someone to touch it up.”
He bounces in his seat and giggles a little, giggles, giggles.
I thought this woman must have been some sort a saint because she didn’t walk out right then and there. I came over to take her drink and she looks at him, looks at me, and goes right for the vodka. As I turn to go fetch for this poor saintly woman Mr. Sloshed waggles his hand at me and clicks his tongue. He orders three bottles of sake. They hadn’t even ordered any food yet and their bill was already over $150.
She sat there awkwardly while he talked exclusively about himself, how important he was, how he was so smart and funny etc. Whenever she brought up something about herself he found some reason to put it and her down and himself up. You could see the pain in her eyes as she awkwardly nodded along while he spluttered and slurred his way through another dull story.
Finally they ordered around fifty minutes later. $275 dollars worth of nigiri. Let me explain, generally the more expensive pieces are around 4ish dollars each. This would be around 70 of those. It’s a fuckton of food for two people. He had filled out the little sheet that we have to mark down your sushi order with a wave of his hand, telling her that she could try a little bit of everything. “The finest of everything for m’lady, different than any other dates you’ve been on. I’m a gentleman and now how to treat ladies right. “You could see her cringing inside as he mimed a dramatic bow and did the rude tongue click to get me over.
And oh god he was drunk at this point, slumping over the table sweating like a running faucet. But still he didn’t stop talking, chattering about how horrible american girls were. German girls were better and all, and she [his date] looked German, was she German? She confirmed that she was in fact Norwegian/German.
The sushi arrived, the giant hoard of sushi that no mortal man could ever eat by himself and they began to eat. He quieted a little while putting a piece into his mouth and when he swallowed, but continued on chewing or not.
He regaled tales of his time abroad in Europe and how wonderful the women were over there, real woman unlike their American counterparts. And then how wonderful they told him his German was, and how he knew just how wonderful his German was.
He brought up some band called Katzen something? I’m not quite sure exactly what it was, but he attempted to impress her with his knowledge of German right then and there by telling her that it meant ‘Cat Screams’. It didn’t apparently. She politely corrected him, and he didn’t like it one bit.
He awkwardly sat up and screamed at her, screaming how he had so much experience in comparison to her on such matters. This grown man was leaning forward with his palms on the table, right up into this woman’s face and screaming on the top of his lungs how she was a horrible b***h and disrespecting him. How she should be thankful that he even considered taking someone as ugly and fat as her out on a date. How he wasn’t like all the other men and he was treating her just right.
At this point the restaurant was empty besides for them, and the kitchen staff, both sushi chefs, and the other waitress were camped out behind the sushi bar watching this train wreck because everything else was already cleaned and closed up but couldn’t leave until the last table did.
Dear god this woman had a face of steel, because she stared him right down until he returned to his seat and resumed drinking and talking about himself.
The check was requested a few minutes later, by him. She requested takeout boxes for the mountain of sushi still left over. It took three to fit in all the pieces that were left.
He barely even looked at it before paying and trying to discuss a second date with her, somewhere a little more private, by his own words.
And she declined, very firmly, getting up and leaving with $170+ dollars with of sushi in tow.
Mr. Sloshed looked totally blindsided by this revelation, shedding angry tears as he gathered his things and trotted quickly off after her, muttering “bitches” and other such things under his breath.
Never saw either of them again.
Image source: anon
#106
Worked at *****. Couple walks in in jeans, ratty t-shirts. Guy pulls my coworker aside, says he wants to propose. They spend 80% of the meal on their phones barely saying a word to each other.
They get like huge meals – we’re talking Ultimate Feast stuff your face this isn’t s**y at all foods.
They don’t order dessert, so my coworker had to bring out the ring on a free drink that we gave them on the house. Coworker sat it down. Girl didn’t notice, too busy playing games on the phone. There’s about 10 of us crowded in the exit from the kitchen watching to see what happens.
One minute passes…two minutes passes. Finally he must have cleared his throat or something and she looks up. Seems to not notice the ring. He, I guess, asks her to marry him. She just kinda says yes. No excitement. They continue playing on their phones for most of the remainder of the meal.
Image source: berlin-calling
#107
Dude was sitting there with this sheepish look on his face as his date sat there in a revealing dress and half a nip slip going on. Extremely awkward approaching that table and maintaining eye contact.
Image source: the_dead_icarus
#108
I have a few.
– I greet this couple with 2 kids. Say my usual “How are you guys doing today?” The man says “great” the wife then looks at her husband and screams “You’re such a f*****g liar, we’re not great!”
– I had a couple, maybe in their 30’s, come in. Im guessing they were fighting because when the guy left for the restroom the girl grabbed his beer and poured it all over his coat, which was sitting in the booth. I actually had to grab the beer out of her hand, her response was “He’ll clean it up!”
– There was a young couple, maybe late teens, straight up making out hardcore. Im talking about sucking face. What was even funnier is the girls mom was sitting across from them in the booth acting like it wasn’t happening.
Image source: novags500
#109
Bit late, but oh well. I was working in a very small restaurant, and there was only about 4 couples dining. One was an elderly couple, who were just sat staring at each other, not eating a single bit of their food. I left them for a long time thinking maybe they would start eating, they didn’t. So eventually I went over to check if they had finished (even though it was very clear they hadn’t) the guy then proceeded to order the most expensive bottle of wine, wait until I had opened it, stood up and shouted at the woman that he had never loved her and that her paying for this meal is the first thing she will have done for him in 35 years, and then left. She sat there crying and whimpering. Was sooooo awkward, especially when I had to ask her to pay, and she told me she doesn’t take her purse out with her.. Had to phone her sister to come down and pay and by this point she had been crying for an hour on my shoulder, very awkward turtle situation.
Image source: lubeycat
#110
My early 20’s , i was serving a couple, early 30’s, not English native speaker (me too btw), looks like a fresh couple. They were friendly but something seemed weird, by the time i bring the drinks the man ask me if I would be interested to date his gf. I said she is very pretty and that they look good together, cause i thought thats what he wanted to know.
But no, he re phrase and ask if i would like to go out and have s*x with her… I was so shy, i went to the kitchen and ask another staff to serve this table.
Well she was looking good, i think i missed a fun opportunity lol.
Image source: awayt22
#111
More embarrassing than awkward but once one of my coworkers walked in on a guy getting a b*****b under the table.
Image source: Pacman1012
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