Dating is hard. Those of us who are married don’t miss it, and those of us who are still doing it rarely enjoy it. It can be incredibly difficult to meet nice people.
The rise of social media dating has made things even more complicated. Even if you’ve never been on a Tinder date yourself, you probably know their reputation.
As for restaurant servers, they get to be on the front lines of all of it. They hear everything, even when you think they’re not listening. They can’t help overhearing things when they come to refill your water glass. And you better believe they have opinions about everything — from how your date is going to what will happen to the two of you in the future.
They hear some really sweet things, and even get to help out with proposals. But they also witness some truly painful and awkward moments. They might be professionals, but they definitely cringe — and gossip about you — when they go back to the kitchen.
Here are 75 servers who took to social media to share the stories of the worst date disasters they’ve ever seen. Can you make it without cringing?
Quotes are in their original form and may contain spelling or grammatical errors.
1. The waitress ruined the surprise
“There was a note in our reservations that it was an engagement, they wanted champagne, a specific seat, bunch of other stuff. The server comes up to the table with something like ‘so I read we’re celebrating an engagement, congratulations’. Confusion from the woman; glaring from the guy. He hadn’t proposed yet. She ruined it.”
2. Will do
“I walked up to a table and was about to drop off the bill, caught the end of ‘it’s over.’ Guy looked at me dead in the eye and said to ‘split that f***in check, right now.’”
3. Rejected twice
“These two were on a date and the guy went to go use the bathroom, The girl just up and leaves after he went to the restroom. When the guy came back he sat around for awhile until asking his waitress where she went. She replied with saying that she left. The guy then asked the waitress if she would go on a date with him. The waitress said no.”
4. Did he really think that was a good idea?
“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, but I did bring out tissues for the wife, who was breaking down. It was a complete surprise to her. I ended up boxing up their dinner. The guy paid, but I do not envy that ride home.”
5. She takes chocolate ice cream seriously
“Had a man and woman sharing dessert and the man playfully put a bit of the ice cream on her nose she then did the same and he did it back once more but with a different flavour of ice cream. She the flipped out at him because ‘you know I like chocolate the most why would you waste it you idiot’. In the end she stormed out cause the man couldn’t comprehend how much she was blowing up the situation.”
6. The worst time to have an accident
“mid1980s: A couple enjoyed a meal at a 2 top that I waited on. All was well, but midway through dinner the area began to smell like someone farted. It did not go away. The man complained, and I apologized, noting that it wasn’t the restaurant and there was little I could do. The woman tried to calm the man down, but he asked for the check early, demanded a discount [which we gave him] and stiffed me on the tip. They left. The woman left a skid mark of s**t on her chair.”
7. Don’t try to catch unless you can catch
A couple came in to my hibachi restaurant since it was the ‘fanciest’ place in town. Young woman was all decked out in a spangly, light blue satin cocktail gown, he was in a suit and tie. They wanted to sit at the grill for the show but still ordered a ton of sushi and drinks so their section of table was extremely full of dishes. I’m talking multiple mixed drinks and waters for both of them, soup and salad bowls for both of them, appetizer plates, sushi plates, soy sauce trays, and their entree plates. The hibachi seats 12 and it’s basically a bar ledge around the grill for a table, and we were slammed so there was no extra room. I barely managed to talk them into letting me take the empty dishes as they finished with them, but it hardly helped. The chef starts his show and dude is super into it, demanding to be included. So the chef flicks a shrimp at him. In his effort to show off and catch it in his mouth, he manages to miss it completely and crashes into the table sending food, drinks, and a full bottle of soy sauce on a plate right into his date’s pale blue satin covered lap and everywhere else. It was a complete s**t show. She was screaming and crying, the other couples that had their meals ruined were all upset, he’s blaming me(?!) The bus boys and I were just trying to clean up and salvage what we could of the service… it was awful.”
8. Just drop it
“She was Japanese and he started off by showing her his shirt with sumo wrestlers on it, then would ask questions like… what’s your favorite sushi? Do you only speak Japanese? How do you say toilet in Japanese? They have sumo in Japan right? Did you see my shirt? It was so amazingly awkward”
9. Take no for an answer
“He proposed, she said no. He cried and tried to change her mind for 20 minutes while she sat there stony-faced. She finally got up and walked out. He paid and left in tears.”
10. So no dessert, then?
“A couple came in to the restaurant I work in last year. They split a meal and looked happy enough. Half way through theyre meal I notice the guy seems upset. He’s speaking louder and faster and the girl seams a little shocked. The guy start screaming ABOUT SUGAR! And how its the biggest problem of the 21century. How her not caring is gonna get all of us killed and it’s her fault. There was a waiter trying to get involved at this point and asking him to stop screaming, the girl was so embarrassed she just left in a hurry, the guy ran out after her with out paying the bill. He came early next day, really embarrassed. Paid the bill, said sorry under his breath and left. Never seen either of them again.”
11. All she said was “Noooo”
“A guy proposed to his girlfriend 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 expensive it cost, the different aspects of it, etc. Finally, the girl just went, ‘Noooo.’ The guy sat back down and they tried to finish their dinner like nothing happened. I caught eyes with our server and he made the most perfect ‘holy hell that was bad’ face. Geez, that was awkward.”
12. Yikes
“I served at a Japanese hibachi restaurant and once had a couple come and the dude dumps her after the meal. She then gets up and throws up a trail probably a good 20 feet as she runs to the bathroom. The dude got up and left the girl and I was left to clean the mess.”
13. Way to make her jealous
“I was working as a waitress in a Sushi restaurant and Valentine’s Day was an all-hands-on-deck shift. This guy I had just started seeing wanted to go out, but I told him that working in food service, you never get Valentine’s Day off and we’d just have to celebrate the day after or the weekend after. Nope. He got so upset that he went and asked a different girl out, came to the restaurant I worked at on V-Day and sat in MY SECTION. He then proceeded to spend the entire evening making a fool out of himself and making his date uncomfortable as he tried to make me jealous. Needless to say we didn’t go out again. Ever.”
14. This is the wrong way to impress her
“It was a young couple, early twenties I would guess. The date started out with a lot of formal and shallow conversations along with a lot of awkward fumbles. You could tell the girl was a little disinterested and started looking around impatiently. Then when I brought them their food, the guy made a comment about how I was a white girl working at a Japanese restaurant. This really didn’t sit well with her, making things even more uncomfortable. When I walked by about 10 minutes later, I saw that he had compiled the wasabi from both his and her plates and decided to eat it in one mouthful in hopes of impressing her. About 5 seconds after swallowing, he started crying and gagging while she just made a face of pure disgust. He got up to run to the bathroom with his hand covering his mouth with vomit shooting through his fingers and onto the floor on the way because he couldn’t keep it down. She promptly left the restaurant. It was pretty fucking awkward.”
15. At least they handled it well
“I was at an Irish pub, and it was a couple’s first date. They are at an outside table getting to know each other having a pleasant conversation which seems to be going well. Then a drunk girl entered and she’s totally plastered. She takes a liking to the guy and decides to go over and join their date. She sits at the table slurring ‘Heeeey you’re cute!’ proceeds to climb into his lap and try to grind on him. Everyone’s watching this slow motion train wreck. He removes her and gently sets her down and continues paying attention to his date. She won’t give up, so he pulls the best move ever: he buys her a shot, she does it and promptly passes out on the table. They continue their date completely ignoring the drunk brat sleeping right next to them. I hope they worked out; I’d love to hear them tell their ‘how I met your mother’ story.”
16. Oh, that’s brutal
“I had a similar one; he was first to arrive, I brought him a drink. We both saw the woman enter, he clearly recognized her as his date and rose to stand, adjusting his clothes a bit, I gave him an encouraging smile, ‘go get ‘er, tiger’….The woman gave him a blatant once-over look from about ten feet away, turned and left. I think my heart broke the same instant his did.”
17. She kept her job
“I had a couple come in one night and everything seemed to be going fine. We just hired a new server 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 jerk! I knew you were cheating on me!’ Turns out the guy was her boyfriend 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.”
18. At least it was beer and not something else
“A couple, luckily not in my section, were clearly on a first date. She ordered a wine and he ordered a beer. The beer was meant to be served in a branded glass but the only clean ones had just come out the dishwasher. The waitress gave him one of these glasses and it must have warm still. She put the glass on the table and poured about half of the very cold beer into it. This poor guy picked up the glass but the temperature difference made the bottom of the glass sheer off. So his whole glass of beer dropped straight down onto his lap. Obviously, the waitress and manager were all over him trying to help but they couldn’t exactly take his trousers and give him dry ones. So he spent the rest of his date soaked through and stinking of beer. They didn’t order starters or desserts, just had a main and left.”
19. Could you be more hurtful?
“When I was bartending, this guy came into the bar on a ; he. He was an average-looking guy in his late twenties. He sat down and asked for a drink and told me he was nervous because it was his first date in three 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.”
20. You might want to pay more attention
“Back when I served food at one of those super touristy seafood restaurants, I worked a Valentine’s Day double shift. For lunch, this younger couple came in celebrating their one year anniversary. I offer my congratulations and proceed to do my usual spiel before taking orders. The girl is looking more and more dismayed the longer I talk. Finally I get to the end and ask if there are any allergies. She looks directly at her boyfriend and states, ‘yes I’m allergic to fish and shellfish.’ Then looks over at me very sad. I made sure every aspect of her meal was fine for her. But It was that look of ‘we’ve been dating a year and he still takes me to a restaurant that could kill me’ that really did it for me.”
21. I would’ve done the same
“In college I waited tables and Valentine’s Day was always a good one in terms of tips. I once saw a couple come in to eat, halfway through the dinner the mans wife shows up to surprise the couple. The wife took the wine bottle and poured the remnants on the husbands head, took off her ring and told the girlfriend she could have him. He tipped me a $100”
22. In sickness and in health?
“I used to be a waiter in a 5 star restaurant it was my first week. One guy was about to propose it was obvious by how much he was sweating he was drenched. I tried to make them both relax. They went on to finish up their meal. As soon as the cake arrived he then went on one knee, she stood up suddenly he vomited right on her high heels. After the shock of what just happened she still ended up saying yes”
23. Don’t order for your date
“Couple sits down at my table. Do the usual greeting. Ask them if they would like to start out with a beverage. The female replies, ‘coke, please’. The male stops her, interrupting ‘uh, make that a diet coke. I’ll take a jack and coke’. The date didn’t get any better.”
24. Did he think she’d be impressed?
“I work at a seafood restaurant, and while I was going over the menu items, he would butt in with ‘facts’ about the meals. He said the Mahi Mahi was a type of dolphin. I said ‘oh, no, it’s called dolphin fish sometimes, but I assure you, it’s fish!’ He said I was wrong and proceeded to tell his poor date it was actual dolphin and he has really fresh cuts of them at his place. Then when looking at our selection of crabs, he mentions he has 10 bags of King Crab legs at his home as well. The entire time he looked in his menu, he either knew everything there was to know about seafood or that he already had ‘fresher, better’ versions at his place.”
25. Just run
“This guy kept saying all this forward stuff to his date, and she was just trying to hide her face in her menu. He would say things like ‘Once this date is over I am going to show you the nasty!’ Poor girl. Anyways she eventually just got up and left while he was in the bathroom. I could have sworn she sprinted out of that Japanese steakhouse, you could hear her breaths of relief as she made it out of the doorway.”
26. That was his hill to die on
“I worked at a higher end place and there was a guy who pulls in the lot in a new high-end BMW. He was a flashy guy; chains on/sunglasses inside type. A girl comes in with him and she’s classy. He walks to a corner table and she walks past him, saying she wants this booth over here. He’s not budging; he says if she wants to eat with him, it’s gonna be at this table. Well, that doesn’t fly well. They end up leaving, he says to me hold that table, he’ll be back in a few. He drops her off somewhere and comes back 20 minutes later and has steak and lobster for one.”
27. Two dates at once
“I had a regular sitting at my bar in a chain restaurant about two weeks ago. He sits there for an hour, leaves for 20 minutes or so, then comes back complaining that he’d been stood up. The date was supposed to have arrived an hour before he mentioned anything. Poor guy. All of a sudden this woman appears, apparently his date. Nothing out of the ordinary except for the fact that she was an hour late, so I continue making drinks for the restaurant. Couple of minutes later and a waitress comes up asking if the woman was on a date with the guy at the bar. I respond yes and ask how she knew. She told me that the woman had just left her (the waitresses’) section and had been on a date with another man.”
28. We’re missing some key details
“I was waiting a table for two teenagers who where probably around 16 or so and clearly on one of their first dates. Everything appeared to be going well until the boy got his head wedged in the back of the chair. Fire brigade were called and after 20 embarrassing minutes he was cut free. Girl went to the bathroom and never returned.”
29. That’s a bit overprotective
“I will never forget when this younger couple came in on a date, that was chaperoned by the girls dad. Yeah totally understandable, maybe even kinda cute if they were pre teens, but no. These two looked like they were soon to be adults, definitely old enough to be on a big kid date. The dad sat himself at this smaller table RIGHT ACROSS THE WALKWAY from the two of them and seriously just stared. Didn’t order anything. Not even a drink. Just watched. It was so cringy seeing the reaction on the guy’s face when he realized what was going on, and how breezy the girl was being. She ignored the elephant in the room but the entire time he had this ‘could you fucking not?’ look on his face. Uggh.”
30. It can be hard
“Had a table of two people, probably in their mid 40s last year. Took 45 minutes for this couple to get their entrees due to our kitchen being way too slammed. When they were dropped at the table, they immediately asked for to-go boxes because they told their babysitter they’d be home by a certain time. I overheard the wife say ‘well I guess this is why we don’t celebrate Valentine’s Day’. The worst part was that they weren’t angry, just… very sad. My personal feelings about dining out on Valentine’s Day aside, I felt so horrible that this couple clearly had put in an effort to have a nice night with each other only to have it go that way. (We comp’d their meals, btw).”
31. She made her thoughts pretty clear
“Couple comes in on Valentines Day – no reservation. They get seated at the bar, order some drinks and apps, and are sitting there chatting and laughing. Seems pretty normal. After finishing their apps, the guy drops to one knee, and pulls out a ring. Girl immediately shuts him down. He didn’t so much as get a word out, before she’s saying, ‘Nope. Nope. Nope.’ Grabs her coat off the back of her chair, and is putting it on, still saying ‘Nope’ over and over. Practically RUNS out of the place, does not look back. He looks gutted. Pays the bill, walks out, staring at the floor the whole time.”
32. Got a date, lost a finger
“A couple sits down to order and I come over almost immediately to ask their water preference. The woman goes to scootch her chair in and, within what was probably a 10th of a second but I remember it as if it was slow mo, when she brings her hand back up I notice a spatter of blood go across the table cloth. Her date notices blood. He yells ‘YOUR FINGER!’. The woman looks down. I look down. Her finger tip, ring finger on her right hand, is gone. Blood is slowly dripping out of the stub and going all over the table. I stand there in shock going ‘uhh uhh uhhhhhh’. They both stand up and the man tips back her chair. The finger tip tumbles to the floor. He then picks it up and I run to get ice and tell the bartender to ask if anyone is a doctor (there were many) and to get the owner. Turns out the front corner of the wooden seat had become disconnected from the hollow metal leg. Chopped it clean off. I swear to God to this day I can never scootch in a chair without thinking about it.”
33. Hope she was okay
“There is the guy whose date got so wasted she fell asleep at the bar and he left her there.”
34. That’ll ruin the night
“A nice lady brought her kid in for dinner. Got seated at a table next to her husband and his mistress.”
35. She didn’t want to be naughty
“Alright so I had a 2 top table with a very handsome young guy and a super attractive young woman (early 20s I think). Anyways I proceed to go over and greet them and discuss the specials for the night. They seemed nice and it looked like it was their first or second date. I asked for their drink order and the guy gets an ice-tea while the woman orders a glass of wine. She then proceeds to tell the guy in the highest pitched voice to order alcohol because she will feel, ‘so naughty if she is the only one drinking, and she doesn’t want to be a naughty girl’. This goes on for a few minutes until the guy gives up and awkwardly just orders a vodka soda. That was the first weird exchange. Next I bring them bread and they devour that shit fast. I ask if they would like some more and the woman says oh yes she would love some but she doesn’t want to be a naughty girl again. She described herself as naughty again for another few minutes until I just left. They place their orders and she goes to order a steak with fries as her side. She again repeats how she is so so naughty for getting carbs as her side. The guy just looks so drained by the end of the night because this woman would not fucking stop saying the word naughty. I could tell he was just pushing through because she was wicked hot and apparently a ‘naughty girl’, but god damn there is a point where the whole ‘high’ pitched fake ‘I’m a naughty girl’ shit gets so annoying.”
36. He didn’t mince words
“A girl sits down at my table in the bar and is waiting for a her first tinder date. They have a couple drinks and she leaves. I think everything is normal… UNTIL… The dude then hands me his card and says, ‘You’re prettier. Call me.’ And proceeds to head into a meeting in the dining room. To make matters worse, she calls the restaurant 10 minutes later to ask me if he really had a meeting to go to or if he was blowing her off.”
37. She made a choice and made it fast
“I was waiting on a couple once, had to be a first date. The guy was constantly a dick to me, and the girl was very apologetic. He asked for a well done filet mignon, when I started to advise him that it would be burnt as such and to ask if he’d like it butterflied, he he flipped his shit yelling ‘you don’t tell me how I like my steak!’ She got up, pulled out a $20, handed it to me, and walked out without a word. He shouted after her to come back, didn’t even get up till she was out the front door though.”
38. Just get over it?
“Ex Barista here, hope that is close enough. Some guy on Valentine Day came in and asked us to write on the cup ‘will you marry me?’. It did not go well. She looked at the cup while he went down on one knee. She said nothing, put the cup back down and just walked away shaking her head. He, on the other hand, got pissed and started to rant about how she should have gotten over him sleeping with her sister already. . . . we had to ask him to leave.”
39. He could’ve let her enjoy her meal
“I work at a semi fancy kind of place and when prom rolled around I had this one super adorkable couple sit at one of my tables and everything was going great for them until at the end of the meal (they both had a big steak entre) I offered if either would like dessert. The guy said no thanks and the girl said she wanted some bread pudding. This guy then says ‘wow’ and just stared at her. I could feel the waves of mortification emanating from her body. The poor girl. She just instantly shut down and stared into her lap. I felt so bad for her and then she gets up and walks away. I stared at this kid, wanting to tell him what a little shit he is. But instead I said, ‘wow, that was insensitive, you just ruined her whole night’ he says nothing and he pays and leaves. No tip. But it was worth it.”
40. Give Hannah a call
“A few years ago, I had finished my shift at a pub I was working at, and sat at the bar with a drink. There were still a few couples sat in the restaurant, but the boss let me clock off early. I had a pint before leaving, and at a table near by, it sounded like a proposal was about to happen, a few people went quiet listening in. Then, it happened. Guy: ‘Hannah, will you marry me?’ He was kneeled in front of his girlfriend, her sat down. Girl: ‘Hannah? Who the **** is Hannah?’ She yelled, threw her drink at him and walked out. Guy paid and walked out, looking very red.”
41. Too many dates
“A couple on a date, sitting having a meal and chatting, just a normal date. A guy comes in who turns out to be the woman’s soon-to-be ex-husband and, at first, justs asks to talk to her. She refuses. He asks louder and she refuses louder. Lather, rinse, repeat, getting louder. The man on the date stands up and tries to calm the ex-husband down. He starts screeching at him and her and everyone around. The ex-husband sweeps all the food and drinks off the table on to the floor and wants to fight the male date. A nearby waiter steps forward to try to calm the ex-husband down. He takes a swing at the waiter. GAME ON!”
42. Mind your own business
“When I came back for their plates, the guy comments that his date ate a lot. I kinda laughed and said something about the food being really good, so I’m not surprised. He goes ‘No, like.. This girl (pointing) barely chewed. She inhaled her meal. And some of mine! HAHAHA!’ At that point the girl looked rather annoyed but still had a polite smile on her face. I went to check on them a while later and the guy seems completely oblivious to the fact that his date doesn’t like his sense of humor. He orders himself a beer, and comments that whilst his date seems to loooove food, she’s not much of a drinker. At that point, the girl looks like she wants to stab the guy. She tells me they’re about ready for the bill. Guy goes, ‘Are you really not going to have any pudding? Are you suuuure?’”
43. He didn’t stick the landing
“A guy did a backflip and asked a girl to be his valentine… she declined. I walked up to him and asked if he was fine, he said it took him a week to perfect.”
44. That’s quite the reaction
“During a shift once another waiter had a table with a couple who slowly started getting louder. They just kept having mini outbursts. Enough that people knew that there was a fight going on, but not enough that everyone was staring yet. Then seemingly out of nowhere, shortly after receiving their food, the dude flips the table, with food and drinks and all, on to her.”
45. SOS
“I work at a fairly nice Italian restaurant, where we do a lot of business. One night a man who I was not even serving came up to me […] and hands me $20 and a napkin with a phone number on it. He proceeds to tell me, ‘I am on the worst date of my life, this woman is horrendous and I have to get out of here. Take this $20 and please go to the nearest phone and call me and tell me that I have to get home right away. I don’t care what excuse you make up, I just gotta get the hell out of here.’”
46. Show some class
“Served a couple a few months ago. Every time I walked over, he would always be the one talking, and she would just be sitting there not having a good time. At the end, I asked if it was one bill or separate and she immediately piped up, ‘SEPARATE.’ I go and take his payment […] and I see the guy take his phone out and start swiping through Tinder.”
47. It’s fate
“While working at a sushi bar in college I witnessed a blind Valentine’s day date where the guy who showed up was already the girls ex-boyfriend.”
48. You’re special, all right
“[I] once witnessed a date where the dude talked about how special he was and how his mind wasn’t like other people’s for the entire date. The girl was politely nodding along and every time she tried to get a word in, he’d cut her off. Absolutely brutal.”
49. He was REALLY hungry
“I was working in a small restaurant with two floors. A woman and a man came in and I had a table for them upstairs. It looked like they had a first date because they were asking those getting to know each other questions. After ordering food, the woman had to go to the toilet, which is downstairs […] She walked down, tripped and fell all the way down knocking her head on the ground. Two colleagues immediately rushed over to her to see how she was doing. She was unconscious and bleeding from her head so they called an ambulance. I went to the man while he already started eating and told him his partner fell down the stairs and that she was unconscious and that an ambulance was on the way. He walked to the stairs, looked down and walked back to his table to finish his food.”
50. He was GONE
“I was bar tending in New York and watched this couple that had met on Tinder have their first date sitting at my bar. The girl was a complete maniac […] Kept telling him he was lucky that she agreed to meet him at all and she didn’t think he’d be this boring. She ordered about 5 or 6 Long Island Iced Teas and several shots; he literally just had 2 beers. She made him pay for everything. My favorite part of this s— show was that he excused himself to go to the bathroom and left through the fire escape. Absolutely brilliant.”
51. He had a lot of passions
“Former waiter here. There was this one date that comes to mind… at first it seemed like it was going ok but then I noticed the girl was starting to look uncomfortable. I decided to pay more attention to their conversation and the guy was talking about how he likes to use moisturizing lotions and hair volumizing spray and if she ever stays over at his place he’s got her covered for hair products. Then he started talking about how he thinks Justin Bieber gets a lot of undeserved hate and how talented Bieber is. This guy tried to hold her hands across the table and she withdrew hers immediately. I could tell she just wanted to leave asap and this dude could too. Then he brought up how rich his dad is and how his dad buys him anything he wants. Then he starts bragging about how he always gets what he wants and she’s just cringing the whole time. I wasn’t able to catch what happened next but later I saw her storming out of the restaurant with this dude just skulking about at his table.”
52. Guess they won’t be getting dessert
“Two failed marriage proposals on the same Valentine’s Day. The first one simply said ‘no I can’t do this,’ and walked out. The second one stared like a deer frozen in the headlights for an excruciating 30 seconds before muttering ‘let’s talk about this later.’ They stayed for the rest of their 6-course V-day special dinner, eating and making painful small talk.”
53. Oh, poor guy
“Old man proposed to old woman. He tried to get off the chair to kneel, tripped and fell and I assume broke something since he couldnt get back up and we had to call an ambulance. My manager had to drive her teeth to the hospital separately because she had taken them out to eat her soup (lord knows why) and left them on the table in the confusion.”
54. That’s terrible
“An older woman came in with an older fellow who had a heart attack and died on their second date. She was in tears but kept trying to talk herself out of it because they’d only met twice. It was a bummer of a shift.”
55. It was too much to bear
“When I was taking their order the guy asked if we had soup because he had mouth surgery a few days prior and chewing food was still a little rough. We don’t have soup, so I explained that the ‘softest’ food on the menu was gnocchi. He ordered the house gnocchi and proceeded to cut each tiny dumpling into four or more pieces and slowly chew each piece. He ate that entire dish over a 3 hour period and the girl stuck it out for the whole thing. She looked miserable and I’m pretty sure they never saw each other again.”
56. Keep your hands to yourself
“Dude would not stop eating her fucking food. Girl looked miserable. Asked if she wanted the rest of her food boxed up and she said no but the guy was like actually yes. It was painful”
57. She stuck around after that
“Ooooh! He made a comment to her about how he’s ‘not jew-y’ so she should order whatever she wanted. She was Jewish. Spent the rest of the evening in silence as he went on about how his ex girlfriend was anorexic and ‘so annoying about food.’ He was happy to be on a date with a woman who could eat like a normal person.”
58. Some people have no manners
“Had an obvious first date where the lady was grilling the guy on how much money he makes and he didn’t really want to answer. It was awkward serving steak and salad during an interrogation lol.”
59. Too much, too soon
“So there was this couple on a first date, seated at a table in the back. At first I didn’t think much of it, wasn’t even aware that it was a first date until the restaurant’s phone rang. A man called to let me know his son was there on his very first date ever (the son was in his late twenties). Obviously this was a big deal to him and he called the restaurant to make sure we would do our best to make sure they have a pleasant evening. My boss heard and instantly went to the kitchen in order to make sure they would get a ‘special treatment.’ What followed was plates with rose petals, red hearts etc. etc. Wayyyy over the top. When serving the plates my boss even mentioned the phone call. To finish it off the desert came complete with fireworks and all that. The idea was sweet, but obviously this was way too much for a first date of two people who were basically just getting to know each other. As the evening progressed the girl was visually put off by my boss trying too hard. Poor guy. Up until then he had been doing quite well, the pair seemed to have a lovely evening. Until my try-hard boss entered the scene that is.”
60. She made the right call
“Oh man, so I actually knew the girl this happened too and she was my table. She arrived with a guy I knew who has a bad rep of being drunk and shitty. Right in front of his date(who is super hot) he tells the host that she doesn’t know him, but he follows her on Instagram. When I’m taking their order, he tells me that he ‘pregamed’ the date at a buddies house. Orders a bottle of pinot and tells my friend its only for himself, laughing. My restaurant has exquisite food, he insults half of it. He tells my friend that he is a sous chef at a restaurant 200 miles north in a big city and is only in town to visit his parents. This is all untrue, I know that he is a busboy at a local restaurant. On his second glass of wine he becomes belligerent, yelling ‘Don’t be a bitch!’ when she says she may not go to a bar with him after dinner. He tried to order another bottle of wine but I cut him off. She ended up paying the whole tab and walking out.”
61. Time to cut the apron strings
“Young teenager brings his girl on a date. They are young enough that they need his mom to bring them. His mom is cool and offers to go sit at the bar so they can have privacy. He tells her no. He then proceeds to talk only to his mom the whole time they were there.”
62. She sounds fun
“I work at a popular chain restaurant and served a couple that had met that day at the grocery store. He picked her up for the date later that night and when I offered them to try our drink specials for the night the women explained that she on some ‘loony’ pills that she couldn’t drink alcohol with. Meanwhile, the man ordered a Long Island and that was the beginning of the awkward tension. She told him, in front of me, that it was unfair for him to be drinking in front of her when she couldn’t. He disregarded this and was ordering drinks from the time they got there. While they were waiting for their food she went to the bathroom. Their food came out and she was nowhere to be found. Eventually, after the man was almost finished his food he asked me to check on her in the bathroom to see if she was alright. So, I walked in to find her standing at the mirror and told her that her date was wondering about her and their food was at the table. She then went on a rant to me about how it was unfair of him to be drinking without her and how he ‘doesn’t want to see her off her pills’ and how she ‘can’t be with a man that will do that to her’ but he gave her a ride there so she couldn’t leave without him.”
63. This is a train wreck
“The guy was wearing plaid sleep pants and a oversized red zip-up Columbia. The woman was dressed more nicely, but it was still casual. All goes well until it comes time for entrées. This guy orders a fuck ton of ribs (a few full racks) and refuses the girl her original order of a house sirlion, which was only about $6, less than a fifth of his order. The man orders a four dollar salad and a water for her. The woman stopps talking completely while the man talks about some crazy party he went to. The man guzzles a few Strawberry Quencher Iced teas, says ‘Seeya Friday, bitch’ and leaves her with the bill.”
64. I don’t think I’d ever recovered
“Not a waiter, but one time my aunt went out with a dude and his glass eye fell out and landed in his food. Best part was she didn’t even know he had a fake eye.”
65. He had a bad thing coming to him
“Every dish had a question, actually, every ingredient had a question followed by a ‘I’ve never had that, have you, is it good? Ewwwww’. I set them up with the pre-fixed Valentine’s menu and were set for food. I’m walking by the table to set up between courses and he’s just shooting down everything she’s saying. She went to college, he would talk about how school was dumb, she liked the squash in the appetizer, he would make comments about why we didn’t just use potatoes, she would compliment the ambiance (we had a classical guitar player), he would keep saying ‘this place isn’t THAT nice (it was). So their meal is over and I thank them for coming in, she’s literally about to thank me and he says ‘hey boss can we get the check? We’re gonna go have some real fun!’ I wasn’t shocked but the look on her eyes screamed ‘OMFG IM SO SORRY’.”
66. Who could have anticipated?
“20 minutes in, he stops me and asks for the check just a few minutes after getting their food. I jokingly asked ‘Uh oh. What did you do?’ Guess that was the perfect question. They get quiet for a second. I realize my mistake. He says ‘Well…It would seem she is not as okay with the fact that I am married as I thought she would be….’ Still trying to keep my composure, I am curious so I go deeper yet and ask ‘Oh….well you’re at least on your way OUT of being married….right?’ Even longer pause. ‘….nervous laugh I should probably just get my check now…sorry’”
67. He sounds charming
“A couple comes in, approximately in their late 40s, early 50s. The gentleman (term used loosely) proceeds to tell me they are here on an ‘Internet date’ and he ‘didn’t realize his date was gonna be a big black woman.’ Needless to say, this was going to be my most awkward table all night. Why the lady (not a term used loosely) didn’t leave immediately, I will never know. They proceeded to order dinner and the guy makes her order a steak, cooked the way he wanted it, and a shot of tequila. He also orders a steak and a shot. He leaves for the restroom as I’m dropping off their drinks and she asks me if I could please call her daughter to pick her up. I give the number to my manager to make the call.”
68. Please don’t do this
“A guy in his 40s with a smoking hot 20 something girl. He had his bank statement on the table and was showing her how much he was worth. To impress her. I think he had like $14k in the bank.”
69. Just stop talking
“I’ve seen several dates– some where the couple was obviously getting along, and some where they obviously weren’t. The one that sticks out the most in my mind was this couple, probably about my age (mid-late twenties). The girl is very cute– little blond thing, big curls, sweet smile– and the dude is classic finance bro, polo shirt, boat shoes, the whole thing. They’re at the table right next to us and this dude proceeds to talk about himself. The whole. Time. He never stopped. She ordered a craft beer and he started going on about how he doesn’t like women who are too ‘high-maintenance’ (he ordered something like Miller, which is silly at a craft beer place), but not one who’s ‘too comfortable with the guys.’ He’s going on and on about his dad’s money and his sweet job at whatever. Doesn’t stop or ask her anything about herself. End story– this date went so poorly that he was still talking and she was so tired of trying to say things and having him just steamroll her that she took out her phone and started checking Facebook. He was undaunted. She left when he went to the bar upstairs because he wanted a rum and Coke.”
70. She was mortified
“Guy was a complete asshat. I assumed this was a blind date or he was completely different on Tinder or whatever app they met on, because the girl looked mortified the entire time. Dude was a douchebag supreme. Completely rude and condescending to me, every time I’d pass their table, he would be yammering on about himself and how great he was. He was just the worst kind of guy. Whenever he would bark an order at me, or bitch about something to me, I could see in her eyes that she was trying to say ‘please don’t associate this asshole with me, I’m a good person.’ When the time came for the check, dude grabbed it out of my hand before I could set it down on the table and said ‘yeah, I’m not paying for any of this’ and pointed to the food he had ordered. It was ‘fucking terrible’ he said, even though he had eaten every single bite of it. The girl’s food? Oh, that was fine, but since she liked her food and he didn’t, and obviously it wasn’t his fault the food ‘sucked’, she should pay for her share. So I got his meal comped, brought back the revised check and handed it to her. She left me a 50% tip, and a small apology note. I sincerely hope that she told that dude to go fuck himself after dinner and the date ended there.”
71. He thought she already ate
“She calls me over when he left and said it was a first date, that he was late and it lasted all of 15 minutes. He said ‘I assume you ate already’ before even saying hi to her, then ordered without even asking if she wanted to eat. She said he talked with a British accent on the phone beforehand, and it was gone when he sat down. She tried to talk to him and he just ignored her, said ‘Yeah this isn’t working’ then booked it.”
72. Get off your phone
“The girl got appetizers and a drink, the guy didn’t get anything. The girl proceeds to talk on the cell phone for an hour plus. Didn’t even stop when she went to the restroom. This was late in the night around when my shift was closing. When I went to leave she was still on the phone and the dude was sitting on the bench next to her…”
73. It couldn’t have gone worse
“When I was a waitress, I witnessed the single most embarrassing thing to happen to a person. Right in the middle of their dinner (and in the middle of our Friday night dinner rush), this poor guy stood up, tapped his wine glass to get EVERYONE’S attention, and then proceeded to tell EVERYONE what a fantastic person his girlfriend was.The whole time this is happening, she was just sitting there with the most bored look on her face. Then the poor guy pulled out a ring, got on one knee and asked her to marry him. She gave him the most disgusted look imaginable and said, ‘This is the ring you expect me to say yes to? Could you be any cheaper?’. She got up and walked out, leaving the poor guy just kneeling there. I didn’t charge him for the meal.”
74. Now that’s low
“Not a server, but a cook. We had a date meet at our bar,. They ordered a drink and food and left his card open as a tab. They rode together in his car, and before they received their food, he told her he needed to step out and make a phone call. She had left all her belongings (jacket,phone,purse, and keys) in his car. He didn’t come back for a while so she went to check on him. She came back, sat down and started crying at the bar. It was slow so I was out watching it all happen too. She had no way of calling him so she tried her phone a few times to no avail. We all thought he was a douche, and since he left his tab open my boss made sure the entire tab went on there and he called her a cab home. Not sure what happened but hopefully she got her stuff.”
75. Does anyone have a dictionary?
“The first thing we heard from this table was ‘Why do you keep calling me pudgy? I’m not pudgy. Do you know what pudgy means?’ We both agree with the girl in this case- she was skinny (strike 1). The couple argued about the definition of pudginess for a while. A little bit later she said ‘Why would you even agree to go out with me if you’re just going to insult me?’ It was because his parents wanted him to (strike 2). They mutually agreed to just finish things off and leave, sat on their phones in silence for a while and left.
75 waiters share the worst date disasters that they’ve witnessed
Cedric Jackson
02.24.20
Dating is hard. Those of us who are married don’t miss it, and those of us who are still doing it rarely enjoy it. It can be incredibly difficult to meet nice people.
The rise of social media dating has made things even more complicated. Even if you’ve never been on a Tinder date yourself, you probably know their reputation.
As for restaurant servers, they get to be on the front lines of all of it. They hear everything, even when you think they’re not listening. They can’t help overhearing things when they come to refill your water glass. And you better believe they have opinions about everything — from how your date is going to what will happen to the two of you in the future.
They hear some really sweet things, and even get to help out with proposals. But they also witness some truly painful and awkward moments. They might be professionals, but they definitely cringe — and gossip about you — when they go back to the kitchen.
Here are 75 servers who took to social media to share the stories of the worst date disasters they’ve ever seen. Can you make it without cringing?
Quotes are in their original form and may contain spelling or grammatical errors.