1. She Looked Miserable
I work in an Italian restaurant. A few years ago I waited on a guy and girl who met for the first time upon arriving at the restaurant. There were awkward pleasantries exchanged at the door and then they were seated.
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.
2. The Breakup Spot
I definitely have seen a lot of awkward last dates!
I used to work at a very small neighborhood restaurant. Everyone that came in was a regular. Most were couples in their 40’s-50’s out for a quiet dinner, but there was one stand-out.
A VERY handsome man in his early 30’s would come in, it seems, only to break up with women. About twice a month he would come in with a beautiful woman and partway through their meal she would be crying. I always tried to clean the tables near them for as long as possible but I never heard much of his speech.
He always tipped well and was super nice to me and my coworkers, it was just brutal seeing him bring in a new lady and knowing what she was about to go through.
3. He Was Nailed
Man and woman cozy in a booth. Different woman storms in through the front door literally dragging two kids behind her, right past the hostess station to stand defiantly in front of the couple and proceeds to BITCH. Dude was nailed.
4. Not “Jew-y”
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.
5. Separate Checks Please!!!
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 as I hand over the Debit machine to the girl, I see the guy take his phone out and start swiping through tinder.
6. “He Might Kill Me” *Teehee*
I was bartending in NY and watched this couple that had met on Tinder have their first date sitting at my bar. The girl was a complete maniac. Kept bringing up the fact that the dude she was with could be a psychopath and could murder her (he had given no indication of this) and went on tinder while he was still sitting beside her at the bar. 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 LITs and several shots, he literally just had 2 beers. She made him pay for everything. My favourite part of this shit show was that he excused himself to go to the bathroom and left through the fire escape. Absolutely brilliant. To be clear, there was only one official entrance and exit. This dude escaped out the back and she went searching for him. Straight up thought he had disapparated out of the bar.
7. Digging For Gold
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.
8. The Hospital As Your Wingman
Well I didn’t technically see it, but it must have been pretty bad.
I work at a hospital and I answered a call on the ward from a patient’s son. He asked how his mum was going, then asked if I could call him back in a few minutes because he was losing reception.
I called him back and a woman answered. I said ‘hello, this is the hospital, is (his name) there?’ She passed the phone over to the same man I spoke to a few minutes earlier and gave him a quick rundown and he said thank you and hung up.
Didn’t think anything of it until the next day when I saw the patient’s son on the ward. He thanked me for calling him back because he was apparently on the worst date ever where the woman wouldn’t stop talking about her ex-boyfriends, all of their flaws, and how much she hates men. He apparently called from the bathroom, went back and left the phone on the table, then went to the bar to get drinks. I called, the bad date answered, and he told her his mum had been in a car accident and he had to go ASAP.
His mum was there for a routine tonsillectomy.
9. A Twist Ending
Olive Garden, around 2014 or so, from like 7:30 – close on a weeknight.
Middle-aged man of sub-average attractiveness was sitting alone at a table with a glass of water, insisting that his date would be “just a few minutes, there’s traffic.” At around 9:15, the manager had to come out and let him know that the restaurant would close at 10, and if he’d like to place a food order, he should probably do it now. He ordered a bruschetta appetizer and said again that his date was on her way and they’d order when she got there.
9:45, this BEAUTIFUL woman walks in and awkwardly stands by his table. I couldn’t hear the conversation they had, but the man then asked for a box for the appetizer and they wound up leaving together without her even sitting down.
10. You Never Know When Racism Will Strike
I was working at a Mexican restaurant at the time. I was waiting on a couple and I could tell it was a first date by the questions I heard them asking each other. Anyway, towards the end of their meal, there was this Hispanic girl sweeping next to their table and the woman looks at her, holds out the remains on her plate and says, “would you like to take this home to feed your kids?” I stood there in complete shock. This woman spoke no English, but she could tell this random woman was completely degrading her. The sad thing is she seemed like she really thought she was doing a good deed. Her date looked so embarrassed.
11. Special Guy Talks Over Date
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.
12. PDA Couple Tips Badly
I work at a Japanese restaurant and one couple comes to mind – it was the “worst” for everyone else involved. we offered “private” rooms that have sliding doors, and this couple clearly was hitting off very well…to the point that after a few drinks, she had moved to his side of the table and they just went at each other’s faces & bodies for about two hours. They could have done all that with the doors closed and it would have been less cringy – still cringy nonetheless – but no, the sliding doors were wide open for all the patrons to see. kids, big groups of people, waitstaff, runners, etc…
If I remember correctly, they tipped pretty bad too, so it was not a fun time.
13. He Ate Her Food
Dude would not stop eating her fucking food. Other table actually noticed and we casually “people watched” the date together. 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.
14. Ice Tea Champ Is Mean To Everyone
Worked at Applebees. This woman was the worst woman I’ve ever waited on. She was needy and slurped down her iced tea like there was a worldwide shortage. He was silent. He didn’t talk once except to order his quesadilla burger, and she just kept going and going, prattling on. And she was mean too! Talking down about how people were losers to be servers, and how much better it was to work in a shop.
At the end, he went to the bathroom and just never came back. He apparently jetted out the side door where the to-go girls worked and gave them a twenty to give to me. Worst Woman was just sitting there and waiting for him to come back. I stood there at the servers station just waiting for her to realize he wasn’t coming back.
So after ten minutes, she just started crying, pushes her chair over, and flounced out. I didn’t get a tip, but it made my night.
15. Country Club Gal Busts Average Guy’s Budget
I work at a country club that is up to its ears in old money that uses said old money to make more new money–the membership fees cost more than a year at my university. To say money is not an issue there would be an understatement.
Anyways, I was serving a young couple and the power imbalance was phenomenal. She was the daughter of one of the board members and the entire staff knew her (read: her father’s) club account was major money. And the gent, well he wasn’t a member, and certainly looked like he was just the average broke college student. He was wearing plain but nice clothes and she was dressed to the nines in fashion. The date seemed to go smoothly enough, nothing out of the ordinary. Until she gets up and leaves the table before I have brought out the bill. I bring the bill to the counter (knowing it is well over $300 worth of food and drinks, all things SHE insisted on ordering–2 bottles of top shelf wine, neither finished–two steaks, when he asked for the chicken and she insisted on him eating steak “like a man”) and he solemnly goes to pull out his wallet and starts tearing up apologizing that he won’t be able to tip.
I mean, I’ve never had a customer cry over not being able to tip. And he further explained he was a server too and that she didn’t know he wasn’t rich and she left because he had told her about his scholarship. I was flabbergasted. And kindly reminded him that at this country club we do not take credit cards nor cash, we only charge to accounts. And so her father got a hefty bill–rest assured he signed a handsome tip to me in her name. (Club policy is that the registered guests may sign for their host member, given that the members have invited them) It was entirely satisfying. Last I heard her father cut her off, I can’t help but smile at all the life lessons she is learning–like working to go on dates.
16. Drunk Blabbermouth Insults Date
I once had a guy come sit at my bar who was waiting for his blind date. He orders a couple of drinks to calm his nerves. Well, he probably should have slowed it down to keep his mouth from working faster than his brain… Anywho…She shows up and is waaaaaay out of his league. She is absolutely beautiful. She orders a drink and they start talking. I come back to check on them and I hear him talking about how much he hates children. He was saying things like how he hopes he never has any, and that he will never be stuck taking care of them, and how he wishes that kids couldn’t be taken into public places so that he wouldn’t have to be around them. She looked him dead in the eye and said, “Well I have a daughter, and I love her very much.” She grabbed her purse and walked out on him. …The look on his face was absolutely priceless.
17. Tragedy Strikes A Man At The Olive Garden
A guy got stood up. He then drank a magnum bottle of red wine (8 glasses of wine) and ate 3 apps out of depression. His date called him and he started cussing her out. He asked for more wine and then I had to cut him off. So he got up and tried to run out of the restaurant with a bottle he grabbed from a rack. An off-duty cop tackled him in the lobby and then he shit his pants in front of everyone waiting for a table. He lied there screaming with the guy holding him down until the cops arrived and arrested him.
This is my fondest memory of being a bartender at Olive Garden.
18. Man Pays Bill, Destroys Entire Family
Used to work as a barman in a pub/restaurant in Hertfordshire.
So this Indian guy is at the bar telling me how he’s meeting his date for the first time, and that she’s also bringing her parents? – possibly some tradition.
Anyway, I’m chatting to him as he’s waiting for the girl and her family to arrive. After about 10 minutes or so they do arrive and are all seated on a table nearby the bar.
I notice throughout the evening how much he’s seemingly making the family laugh and seems to be getting along really well.
Now, the fun begins…
After dessert, the mother and father of the girl go to the beer garden outside leaving the couple alone. After a moment or two, the man comes up to the bar and, with a cheeky smile on his face, asks to pay the bill. Without hesitation, I process the transaction and congratulate him on how well his date appeared to go.
He returns back to his table and takes a seat. The girl’s parents now return from the garden with glowing smiles and rejoin the table.
I notice again how they all appear to be chatting and laughing until, suddenly, the man brandishes his receipt for the meal.
The mood changed instantly, the glowing smiles replaced with looks of anger and disgust. The girl’s father stands up and shouts ‘HOW DARE YOU DISRESPECT MY FAMILY LIKE THIS!’ (bearing in mind this is a small country pub/restaurant, it grabbed the attention of all).
The man then sheepishly exclaims his apologies in the deadly silence to the father, to which he replies ‘YOU WILL NEVER SEE MY DAUGHTER AGAIN!’
Following this, the father picks up his coat and turns to leave whilst demanding his wife and daughter leave with him. The wife stands up and immediately follows him out of the door.
The girl hesitates, half-rising from the chair, and then decides to remain with the man where she now bursts into tears. The man was clearly overwhelmed with embarrassment and shock he did not know what to do, or how to react so proceeded to pat her on top of her head.
After around half an hour or so of her crying she eventually stops and decides to call a taxi to go home explaining how she was ‘sorry, but I have to go with my family.’
The man, clearly downtrodden at this point, reluctantly agreed and called a cab for her.
Now… fast forward about 3 hours to when I finish my shift (approx 1 am) I leave the pub and walk to my car in the car park. At this point, I notice a dark figure sat on a bench near my car. Apprehension rising, I aim trying to decipher the person sat before me, only when I am around 10m away do I notice it’s the man from the date.
He was balling his eyes out… Turns out his date was now locked out of her house for the night as the parents were clearly distraught with her, AND when the parents had left they had slashed the poor guy’s tires so he couldn’t even drive home!
Talk about a date gone wrong… all over paying the bill!
19. Alcoholic Ruins Date
My bar has two floors, and on this night I was working upstairs. Couple came up with beers they already had bought, and sat in my section. I go to introduce myself, girl seems nice, guy says nothing, just stares at his beer.
They eventually get another round, and as I’m dropping off their drinks, I hear the guy slur out “chank youuu vurry mush.” …Fuck. He’s wasted. It was just a beer anyway, nothing too strong, but it WILL be his last round.
I go about my business for a while. At one point I glance up at their table. The girl is gone, and the guy looks like all hell. I thought to myself “Damn, he looks like he’s about to–” and right then, he hurls. Not a lot came out, and he tried to pass it off as a cough, but I saw enough pour out of his mouth, onto his chair and the floor.
I grab my barback and a trashcan. Barback gets to work on the vomit (I love you D, wherever you are), and I put the trash in front of the guy. I told him to go to the bathroom, take the can with you on your way, then gtfo. He says nothing, just stares at his phone for a minute, then gets up and leaves.
I race around looking for his date. I found her at the bar trying to pay her tab. I tap her on her shoulder and try to tell her about her date, but when she turned around, her face told me everything. The shame and embarrassment that glazed over her might make one think she was the one who just tossed her cookies. That’s when she told me it was their first date. They had met through a mutual friend, and she really didn’t know him at all.
My bartender and one of our awesome regulars overheard. We paid her tab. She ended up staying at the bar hanging out for a while as the aforementioned regular bought her more drinks. Real nice lady.
20. A Date With Mom
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.
21. She Said “Yes” Then Slapped Him
Straight up someone proposed last year during xmas service, everyone’s clapping and cheering the guy on, she says yes obviously, the night continues. When they were leaving I seen her give the ring back to him, slap him and jump in a taxi without him. Dude just sparked up a smoke and walked away. To this day I have no idea what happened.
22. Girl Does Not Get Her Coke Or Pepsi
I’m a waitress at a mid-range priced bar/grill. Just yesterday, a younger couple came in, and as I greet them I ask if they want anything besides water.
Conversation is as follows…
Girl: May I have a Coke? Or Pepsi?
Boy: God, Erin. I’m paying.
Girl: Water will be fine actually.
My heart immediately sank, because you bet your ass he tipped less than 10% too.
23. A Disaster From The Jump
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. I suggested her taking an Uber home she informed me that she didn’t have her wallet with her so she was stuck. She told me to tell her date that she just had her period really bad and didn’t have a tampon… I told him what she told me to and at that point, he was finished his meal and just patiently waiting for her.
She eventually came out and started arguing with him over his “drinking problem” and started to get defensive and mad about her “ditching” him in bathroom. After making a huge scene he stormed off and left her there (he had already paid their bill before she got back). So now this crazy woman was stranded at the restaurant with no wallet at midnight. She started wandering around the restaurant asking every table for money, asked every server for a ride home, and following people to their cars on the way out of the restaurant wanting a ride. My manager eventually kicked her out for soliciting and then called the police because she was trying to get into employees’ cars with them.
24. Waiter’s Crush Gets Consoled
Had a girl come into the bakery I work at to meet a tinder date. This girl’s cute and I had been crushing on her for a long time, so I was getting pretty antsy about watching her go on a tinder date at my place of work. Anyways, about 20 minutes into her sipping her coffee, her date walks in the door, takes one look at her, turns around and leaves. She’s starting to tear up while she dejectedly takes bites of her muffin and I am trying to peel away from the rush of customers to go console her for a second while wiping down tables. Before I get the chance, a guy who also saw the whole thing sits down with her and they get to talking, and eventually leave together. That was two years ago, they’re getting married now.
25. Every Girl’s Nightmare Valentine’s Date
Couple is on a first date on Valentine’s Day. I was working at a fine dining Mexican spot in down town Los Angeles. They come in, have a reservation, and sit down. I felt bad for the guy because he was just clueless as to how much of a douche he looked like. His outfit just didn’t match and he looked messy. The young lady was a beautiful woman in her late twenties. I approach them and start to talk to both of them. He cuts me off to ask questions like, ‘what are the specials? Do you have anything special for Valentine’s Day? What’s good here?’. It was clear he’d never been to a fine dining restaurant before but, hey, no big deal, I can help the guy, so I thought.
I assure him we do and do my spiel, not to be a douche but I was good at what I did so these people just had to sit back and relax. I would make sure they enjoyed their meal. The woman is looking at me attentively and trying to get him to let me talk. 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’. I drop off the bill and could see him a bit flustered when we looks at it. There were tiers to the prefixed meals and they got the lowest one and a single round of drinks so his bill was a little over a hundred dollars. Still really good deal for what they got. You can see the lady is trying to pay for some of the bill but he refuses. He gives me his card and I run it. I drop it off and she immediately thanks me profusely. He seems upset with me, I’m assuming over the bill, and says ‘yeah, thanks’. They pass me on their way out and he thanks me again, a bit more genuine this time, and the woman is B lining it for the door, he extends his hand to shake mine and when they meet I feel something in his palm. It was cash. This has only happened to me a couple of times but you close your fist, put it behind your back, and thank them again. I knew what was coming so I walk over to the table. I open the check book and there’s a 0 on the tip line. I open up my hand and there’s an old, crumpled, folded $5 bill. I’m assuming he folded it up at the table, told her what he was going to do, and she was embarrassed so she left ASAP. I start to laugh, it’s not a big deal. I’m going to make up for it later and even if I don’t, it was a cool story. I start to tidy up the table and a $20 bill falls out of the ladies napkin. I appreciated it but felt bad for her. I remember thinking, ‘dude, you should have caught her when he was in the restroom, empathized with her, and asked her if she wanted to grab a drink after’. She was a really good looking older lady, not older in general but I was 21 at the time.
I doubt there was any fun had that night and that guy still probably tells the story of the “stuck up bitch” that never called him again after he took her to a really fancy dinner.