Not all dates are guaranteed to go well, but these servers have seen some absolute stinkers in their day. Some dates were destined to go bad from the start, but some of these dates went so well, they managed to make everyone in the restaurant uncomfortable. We'd hate to be seated next to these messed up dates!
(Content has been edited for clarity.)
He Accepted Her Big Secret, But It Wasn’t Enough
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“I served the overnight shift at IHOP for about a year and was privy to many awkward dates. However, herpes girl is my fave. These two came in around midnight. The girl had just revealed to the guy she was with that she has herpes. And they told me all about how she’d gotten it, how he was so in love with her and didn’t care, etc. It escalated into an argument between the two of them for some reason, and she left the IHOP, leaving the guy there by himself. He ended up walking away into one of the biggest snowstorms we had that year after refusing to let me call him a taxi. It was so nasty out, and the middle of the night, too.”
“I Know Her, But That Is NOT Her Husband”
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“It was a slow day, so the rest of the wait staff and I were just horsing around, talking and laughing when this couple came in.
They sat next to each other and continued to do all that couple BS.
One of the women I work with pointed to them and said, ‘I know her, she’s married, but that’s not her husband though.’
I just laughed, but I turned back in time to see him in the process of checking her gag reflex with his tongue while groping her chest, all while the waitress was in the middle of taking the order.
This was the waitress’s first day working her table, and she just stood there, shocked.
They managed to order, and when she brought the food out, they didn’t say anything, they just start making out again.
Then it got worse.
She took a bite of her food, didn’t even chew it, kissed him, and then he was chewing. She pulled a ‘mama bird’ and fed him.
Then it got to the point where she was tossing him off. The waitress paid me $5 to check on them and give them the ticket.
I went over there and stood where I couldn’t see anything. But it was obvious he was going to town on her, too. I placed the ticket on the table, and they asked for more napkins, which I supplied.
Finally, they left, she now had her hand down his pants pinching his butt. They paid and left as she talked on the phone to her husband.
This woman was ugly and fat. I don’t see how she could have a husband AND a side piece.
I refused to clean that table.
And yes, we told our manager. He just went back into the office and watched the cameras. I’m convinced he likes to watch.”
The Way She Spoke To The Waitress Was Totally Uncalled For
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“I moved to a big city at a young age and was working at a neighborhood type restaurant. One of my regular customers came in with a new girl, and I was just being friendly and chatting with them. The girl must have thought in my friendliness that I was hitting on her boyfriend or something (which I wasn’t) and interrupted me, saying ‘Um, could you just bring me my burger, bimbo?’
I was so taken aback that I think I just said, ‘Ok,’ and walked away.
A few weeks later, the guy came back and was like, ‘I’m sorry. She was awful. I broke up with her.’
My second favorite story happened when I was working at a Greek Diner place in college and was serving this girl who was still waiting a while for her guest to arrive. After about 45 minutes, this guy finally shows up, and they ordered. It was clear that they were breaking up, as she was crying and he looked super stone-faced. I just kept awkwardly filling their water glasses, trying not to embarrass the crying girl. Well, eventually the dude got up and left his entire bowl of chili sitting on the table and, being a broke college student that doesn’t believe in wasting food, I asked her if she wanted me to wrap his food up to go. She replied, while sobbing, ‘No. He doesn’t want it anymore!’ It was so sad and pathetic; I couldn’t tell if she was talking about herself or the chili.”
He Got Back On The Horse Too Soon
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“I was a server at a crappy Italian place that was only open for a year and had three owners. One owner had lost his wife to cancer a few years before and was trying to get out there again. He had been seeing this one lady recently and decided to reserve a table at the restaurant for Valentine’s Day. They sat in my section that night. Instead of it being just the two of them, they brought her two kids (from a previous marriage) with them. They were between 8 and 12 years old. He began crying during service. It was incredibly awkward for everyone. They left early.”
Even The Server Noticed Something…Off About Her
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“There was a couple once; I will always remember their faces. The guy was a tattooed dude without any hair. The girl was tall, actually quite beautiful, and she was wearing a beautiful dress. But it was obviously their first date, and the guy seemed ticked. I brought over a menu, and then I knew why. It was obviously a tinder date, and the girl was transgender. You could never tell by her looks, but when she talked, you knew it. Well, the date was awkward, and they barely talked. I bet the guy was just too nice to say no to her. He paid.”
Not In Front Of The Children!
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“I had a table a few weeks ago where the dad was upper-middle aged, and the wife was…lower middle aged (like 50 and 30, it’s not that crazy). They were with their kids, who sat on the other side of the booth. They were pretty normal until I dropped off their change, after which they sat there for a full five minutes (which is way longer than it sounds) just making out in front of their kids and the rest of the restaurant. Like, arms around each other, you could see their tongues, making out.”
When He Found Out His Girlfriend Was Cheating, He Went Nuts
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“I work at a high-end steakhouse, and I was serving a couple, they were the last people in the restaurant. Suddenly another car pulled up, and a guy came to the host stand, telling us that his girlfriend’s car was in the parking lot. We had no idea what was going on, but he barged past us. He found his girlfriend with her date and punched the guy in the face. We asked them to leave and called the cops. Then we sat there, watching them out in the parking lot fighting when suddenly the guy punched his girlfriend in the face. Crazy! At that point, we started talking about going to help her, but we didn’t feel it was smart or safe to go outside as there weren’t many of us staff there.”
Three’s Company Gone Wrong
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“I was taking tables while bartending. A lovely couple in their late 20s sat in my section. About 30 minutes into the date, a third person arrived.
Apparently, he was caught cheating, and his girlfriend just busted him. She was screaming about how he ruined two years of her life, how could he do this to her. After she left, the guy said they’d broken up a while ago, and she was crazy.
Also, she keyed the crap out of his truck. We offered to give him the tapes if he wanted to press charges. He declined. Made me think he was lying about being broken up.”
She Was Left, Alone And Penniless
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“I wasn’t her waiter, but a waiter in the restaurant at the time. An attractive girl was on a first date with someone she met online. They had driven down to the city from upstate, about an hour and a half away to enjoy a nice dinner, a night on the town, and then get a hotel for the night. They got a table inside the restaurant, and from a distance, it looked like they were hitting it off. I should mention this was an upscale, casual steak restaurant not some Sizzler’s establishment. About halfway through their meal, he excused himself abruptly. She began to tear up and was resisting the urge to cry in the middle of the crowded restaurant. She sat there, stunned, for maybe 10 minutes. I heard from her actual waitress that the guy had stormed off, calling her a nasty name, and took her purse with him, which included her wallet and her phone. After sitting there for 10 minutes hoping he would come back, she started to look desperate and began to ugly cry. How was she going to get home, pay for dinner, or contact anyone? At this point, the entire restaurant staff knew her situation as this kind of news travels very fast.
Long story short, everyone in the building felt terrible for her. No one deserves to be stranded an hour and a half away from home with no money or phone or idea as to why they were being left. The restaurant bought her meal. They also called her a cab when she was ready to go. The staff, especially the bartenders, gave her a whole lot of free drinks after this dude left her and took her stuff. Still a crappy situation though.”
Those Guys Weren’t Too Interested In Their Wives
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“I worked at an Applebee’s for almost a year. Now, most of you think Applebee’s is just a crappy restaurant that microwaves all of its pre-packaged appetizers and entrees. Well, let me tell you, it’s much more than that. It is white trash fine dining. Anyway, on to the date!
It was a double date, and I could tell immediately that both couples were super religious. The men were wearing cheap suits, and the women were modestly dressed, and seeing as this was in Arizona, I was convinced they were either Mormon or Baptist.
What was so awkward about this date? Well, it seems pretty obvious from the moment I got to their table that the husbands were actually on a date with each other, and they’d just brought their wives along.
These two guys were pretty obviously gay and were married to plain looking, chubby, unattractive women as a cover. I felt bad for the women, but based on their appearance (not just looks, but clothing attire and demeanor), it seemed pretty obvious guys weren’t waiting in line to marry them. I’m sure they were happy that their husbands did, even if the husbands seemed to have an unnaturally close ‘friendship.'”
It Was The “Saddest Meal He Ever Waited On”
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“I once waited on a guy on Valentine’s Day who was waiting for his date to show up. He had to be middle-aged, in his 40s perhaps, and this was in the days before cell phones.
Anyway, it was a busy night, and he kept checking his watch, and he had a rose sitting on the opposite plate. He kept waiting, and waiting, and waiting. He more and more sad as the night went on.
He eventually ordered a meal, by himself, and it looked like he might cry by the end of the night. I may have been a jaded little punk most of my early-20s, but I paid for his meal out of my tips that night. It was one of the saddest meals I ever waited on.”
They Definitely Should Have Picked A Different Restaurant
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“I used to wait tables at a fine dining place in a casino. Somehow, this became the town’s universal location to bring your side piece.
There was a couple that both actively had affairs. No big deal, it’s common. The issue was that this was both of their favorite place to bring their paramours. They often dragged along someone other than their spouse, and the staff just assumed they had some agreement.
One night, they both had dates, and chaos broke loose. They were cursing across the restaurant and crying on the wife’s part. I’m not invested in anyone’s love life, but if you’re gonna cheat, make sure your wife isn’t meeting a guy at the same place.”
“And What Would Your Wife Like?”
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“I learned a valuable life lesson about never assuming anything about a couple. This interaction took place in San Diego:
This couple was sitting closely in the booth, gently touching each other, whispering and making goo-goo eyes at each other. I took his drink and then asked, ‘And what would your wife like?’
He promptly replied, ‘I don’t know, she’s in Chicago.’
The lady went off on him about ‘how long are you going to string me on,’ and ‘you promised me months ago that you were getting that divorce.’ She got mad; he got mad, I got the heck out of there. She stormed out of the restaurant. He followed.”
He Quickly Realized This Date Was A Dud
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“I worked as a head waiter about a year ago. I helped one couple out, finding their seat and all that. The guy was nice (average looking, considerate, that kind of guy). The lady was not; she didn’t look up from her phone unless she complained about something. So she never talked to him, only to the staff of the restaurant.
It ended with her asking me to check if her coat was still there (she was worried that the coat-check-girl had stolen it). He replied, ‘That’s enough. This is the worst date I’ve been on,’ and then he left. I was the one checking the door, so, naturally, I let him leave just so the lady would be the one standing for the check. She tried to sneak out after that, but the coat-check girl didn’t let her get her coat back before she had paid the bill (which was a lot, considering there was like six glasses of bubbly on there). Karma’s a witch, as one would say.”
Their PDA Made Everyone Uncomfortable
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“One time, I served a lesbian couple at a small family-owned restaurant. They were both sitting on opposite sides of the booth, and they were cool girls (they were about 17). At one point, I came back to the booth, and they were on the same side all of a sudden. Eh, whatever. That wasn’t what surprised me. What surprised me was how overly touchy-feely they were with each other when I was around while I was standing there. They were all over each other to the point where I was uncomfortable ‘interrupting.’ I hated that table. I would come over to check on them occasionally to find them making out and groping each other. As a waitress, it was pretty awkward to have to constantly interrupt their ‘personal’ time at a PUBLIC restaurant, and it was frustrating that they didn’t even stop when they saw me come over. Every time I would have to clear my throat or speak for them to stop. I was grateful as heck when they left. Those girls had no shame. It’s one thing to be a romantic couple enjoying dinner and another to be entirely inappropriate and make the people around you uncomfortable.”
“There Was Immediately Some Tension”
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“I sat a couple, and there was immediately some tension. When I checked back if they were ready, the male asked his female companion, ‘Do you know what you want?’
She replied, ‘I dunno, everything looks gross.’ I gave them a few more minutes.
They ordered, and a bit later I came to tell them that their order wouldn’t be much longer. This was when I notice that the female was no longer seated at the table. The male asked if he could switch his order to go. ‘Sure I can have them boxed up,’ I said, to which he clarified:
‘No, just hers. I’m going to eat mine here.’
I didn’t see her again. He quickly ate, paid, and left with her boxed up chicken Caesar.
And yes, our food was kind of gross, but she was still a jerk.”
None Of His Dates Were All That Interested In Him
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“This guy would come into the restaurant with a different girl every week. It always seemed like it was a Tinder or OkCupid blind date. The girls were always pretty cute, but he wasn’t very good looking at all but seemed like a guy who’d put in mad effort with angles and a good camera. He became a running joke since we wondered if we’d ever see him on a second date.
The hottest date I ever saw him have arrived, and you could just see it on her face this look of surprise. Her thought process from ‘What the what?!’ to ‘This is what you look like?’ to ‘I’m never going on Tinder again,’ to ‘Why did I waste my time getting ready?’ He wanted to go into the restaurant; she wanted to stay at the bar because she ‘had to go somewhere soon.’ They went to the restaurant, she ordered a Perrier, drank it and left. He ate his all-you-can-eat lunch and went on his merry way to return the week after with a more successful date.”
At First, They Thought They Were Father And Daughter
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“I was working a table over from a table that looked like a father-daughter date. The girl was probably 20 and the man definitely over 60. Fast forward 30 minutes and the mother of the ‘daughter’ shows up. The mother was meeting her daughter’s new 60-year-old boyfriend. Mother was yelling and causing a scene for the entire restaurant. She ended up flipping the table and running out of the restaurant. The cherry on top of the story is that another couple had scheduled engagement at the restaurant that night. Thankfully they never showed.”
“If This Was The 50’s, He’d HAVE To Pay For Me”
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“One time, as a waiter at Ruby Tuesday’s, I served one couple (older man with a much younger woman). The entire time, the woman would just whine and complain about everything, and it was obvious the man was getting fed up with it. Finally, when I brought them the check, the guy started reaching into his pockets, and then proceeded to tell the girl he forgot his wallet and asked if she could pay. She grabbed her cards and handed me the bill, saying, ‘You know, if this were the ’50s, he would HAVE to pay for me.’
After dealing with this woman for the better part of an hour, I really couldn’t help myself, so I told her, ‘If this was the 50’s, he could hit you for saying that.’
She didn’t leave me a tip, but on his way out, the guy pulled out his wallet and slipped me a $100. He was still laughing on his way out.”
