Servers get a front row seat to date night, so they've gotten pretty good at spotting couples who won't last a week, let alone a lifetime. These poor people should have saved themselves a lot of time and heartache and just broken up after these dismal dates.
(Content has been edited for clarity.)
The Date Went So Well At First, Then He Suddenly Left
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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.”
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 obviously waiting for his date to show up. He had to be middle-aged, 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 got sadder 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.”
She Came Clean About Her Disease, But It Wasn’t Enough To Save The Date
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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 favorite. 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.”
His Proposal Didn’t Go Quite As Planned
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“I worked at a restaurant in a hotel.
One day, a guy came into the restaurant and asked if I would help him propose to his girlfriend, who worked at the front desk. He gave me his phone and wanted me to record it.
I hit record, and the guy went over to the desk. His girlfriend was surprised. He got down on one knee and proposed. She blushed and said, ‘What are you doing? Stop. Stop! Stand up!’
He asked her again, and she said yes while dragging him outside.
The next time I worked with her, I asked her how he was. She said, ‘I broke up with him. We were not even dating. We went on three dates in one month, and he proposed to me. Dude, you are not allowed to be part of any more proposals.'”
After That, He Had To Take A Cab Home
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“I once was taking the order of an older in their couple 50s or 60s. I don’t remember what the lady ordered, but the guy ordered a ribeye. The wife looked at him and said, ‘Dear, what about your heart? You can’t order a steak!’ Then she looked at me and said, ‘He’ll have the Chicken Caesar.’
The dude looked at her, then me and said, ‘Nope, bring me the steak.’
At this point, I was in shut up mode and just stared at them. She said, ‘If you order the steak, I’m leaving.’
Again, the dude looked at me and said, ‘Make sure its medium rare.’ His wife told him to screw off and bounced. He just said, ‘Cancel her order but go ahead and bring me mine. Oh and when I’m done, could you call me a cab?’ I told the cook to make sure that was the best ribeye he ever cooked since this dude was going to be paying for it for days.
The guy ate, tipped well, thanked me, and took a cab home.”
Even The Server Noticed Something…Different 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.”
“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 darn divorce.’ She got mad; he got mad, I got the heck out of there. She stormed out of the restaurant. He followed.”
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.'”
They Obviously Weren’t On The Same Page
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“I was serving a table of two men once. They were both definitely on the ‘geeky’ side, and this was before ‘geek chic’ became a thing. One was a slightly heavy set white guy with longish hair and a bit of scraggly facial hair, and the other was a thin, Asian man. The white guy was wearing a t-shirt and jeans, but the Asian guy was much better dressed, especially for a Ruby Tuesday. He had a button up shirt and slacks, shiny shoes and a thin silver jangly bracelet. I happened to ask the Asian guy what he wanted to order first, and he giggled a bit and said, ‘Oh, he can order for me,’ gesturing to his companion.
The white guy looked a bit surprised and was like, ‘Ok?’
And the Asian guy said, ‘You know what I like,’ with a little flirtatious wave of his hand. It was at this point that I realized only the Asian guy thought they were on a date. I was mortified but soldiered through getting their orders and being as ghost-like as I could. The Asian guy spent the entire meal gazing in rapt, starry-eyed wonder at the white guy. They paid and left, and I never saw them again, but I sometimes wonder if that white guy wound up getting some that night.”
His Girlfriend Is A Total Third Wheel
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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.”
His Young Date Had No Idea What The 50’s Were Really Like
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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.”
They Had Vastly Different Opinions On How The Date Was Going
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“Just a couple days ago, this couple came in and told me it was their first date. He ordered her food and a drink for her. She got a bottle, and he got a tallboy. She sipped on her drink and seemed to be at least having an okay time, but he started knocking his back. By the time the food arrived, he had a six-pack, while she was only about a third of the way through her first bottle. He drank two more tall boys during the meal, ordered dessert, and switched over to sit next to her. She was visibly uncomfortable. He was blissfully unaware, as he was having a great time. He kept calling me over to tell me how great the date is going. I exchanged glances with her and saw a different story. He tipped alright, though. I just wish I could have helped, but what was I going to do?”
She Was So Horrid, He Just Bailed
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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.”
He Really Needs To Get Out Of That Relationship
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“He was looking at his face in her compact; I made a joke about his make up already looking perfect. He said he was looking at the black eye she gave him. She laughed and said she beat the crap out of him. He looked sad yet resigned to his fate. She told him what to order, said he didn’t need another refill and told him to pay. I didn’t know how to react, but it made me sad.”
They Definitely Should Have Picked Different Restaurants
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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.”
He Was Totally Unimpressed With Her Snotty Attitude
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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.”
“There Was Immediately Some Tension”
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“I sat a couple, and there was immediately some tension. When I checked back if the couple was ready, the male asked the woman, ‘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,’ 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.”
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.”
She Only Did It To Save His Pride
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“I wrote ‘Will you marry me?’ on a dessert in chocolate sauce for a man who was proposing. The girl said yes, but she was utterly taken by surprise in a bad way. She looked uncomfortable and was saying yes to save him from embarrassment in front of the people at this crappy small-town restaurant. I learned that they broke up the next day.”
Her Mom Was Not Pleased To Meet Her New Boyfriend
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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.”
He Should Have Waited Longer Before Jumping Back On The Horse
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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.”
