10+ Servers share the funniest dating mishaps they've witnessed: '[She] was actively on a dating app during the date!'

Author image for Ben Weiss
Ben Weiss • Writer and Editor
Jun 5, 2025 2:00 PM EDT

One of the perks of being a server is that you become privy to a ton of information. You get the opportunity to hear about all the drama from people's lives, all the bickering, and all the secrets. Let's be real: Gossip is a human need, and it's especially fulfilling when you yourself are not affected directly by it. Personally speaking, the best drama is the kind where you don't have a personal stake in it, but you can babble with your friends about what someone did or should do. This, of course, is especially true of complicated romantic relationships. 

Servers certainly have to deal with a lot of nonsense and poor treatment on the job, but if there is one silver lining, it's that they get to hear some memorable drama. These servers shared the most memorable first date debacles they have witnessed while in the middle of shifts. From narcissistic folks to cheaters, it's hard not to forget these stories…

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    Answering an emergency phone call during a first date is always a risk...

    Master_Air_8485 • 13h ago I remember this one time a couple were on their first date, the restaurant was empty, and the guy was a regular, so I made sure that they had a great experience.
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    Hooked them up with a free app and some wine, let the lady play her music on the speakers. When I was bringing them dessert, she got a phone call and she was told that her father had d_d. It went from a near perfect evening to probably the worst night of her life.
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    No one likes a one-sided conversation!

    Silly_Accident3137 • 14h ago Former waiter here. The sheer number of dates I saw that were just one person going on and on and on about themselves and not asking the other person there a single question was mind-blowing.
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    But I think the worst one I ever saw was when a guy asked the person he was with to quickly run lines with him for an audition he wanted to do. I think he thought it was some kind of flex, like he would be impressing his date by slipping in his amazing acting skills before their food arrived.
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    Not surprisingly, perhaps, his acting skills were not so amazing. And then he said "what did you think?!" and instead of waiting for the answer, started explaining the brilliance behind some of his acting choices while his date was forced to half- heartedly nod along and praise the performance. It was so painfully awkward.
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    At least one decent person was kind to this singleton...

    NillarGorillar • 13h ago . Had a customer who was meeting a guy for a blind date. I saw a man walk in the room, scan the room, and walk out. After a couple lonely glasses of wine, and
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    constant checking of the phone, it became apparent that he bailed. I asked if she wanted to order a meal and she declined. I gave her a dessert and told her the bill had been taken care of.
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    Ben--Jam--In ⚫ 13h ago . Had a girl I went on with the night before come into the restaurant I was working at the next night on a different date & sat in my section → She did not know I worked there. The look on her face was priceless when I said "Hey folks, my name is Ben & I'll be taking care of you tonight."
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    Free piece of advice: Never order for someone unless you have been specifically asked to do so!

    MissHillary 10h ago . Man tried to order for his date, she didn't like that but it was early in the date so she said nothing, he ordered an expensive appetizer that she didn't want, only he ate it. She looked not impressed
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    but still seemed to be trying to feign interest. Came time to order dinner and he tried to order for her, something expensive, surf and turf. She said no thank you, she was a vegetarian (apparently established before the date)
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    and wanted the vegetarian dish. He didn't back down and insisted she have the surf and turf. She again said no, she wouldn't eat it. He countered with "he could afford it so why not?!" She left.
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    This lady sounds like a true chameleon!

    vt... 12h ago Edited 4h ago . We had this one older lady come in every week. She wore a different wig every time. Should would ask to sit at the same exact table and ask that we would act like we've never met her before.
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    Then, throughout the day, sometimes the entire day, she would have multiple dates. These men would just fawn all over her. If they did not bring her flowers, it was a wrap. She would ask that we help sneak her out of the restaurant until the guy left.
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    Sometimes it got real awkward. She never paid. She also asked that we only address her as Tiger. It was weird.
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    What's the point of going to a restaurant then?

    ElHamburglare ⚫12h ago I've seen a bunch but the best was when a guy brought in a canned Pepsi and just asked for a glass with ice. He then offered one to his date. It did not go well.
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    Our guess is that the dude definitely was responsible for her abrupt exit.

    InbhirNis 14h ago • Not a waiter, but I did once see a woman storm out of a date in a very nice restaurant. The couple was seated at an adjacent table to me. She got up abruptly and left, just before the food was served.
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    The waiters seemed to handle it very discreetly: they brought a cover to keep her meal warm in case she returned, and after a generous interval, quietly took her plate away. The guy waited for a while before forlornly eating his own meal and asking for the bill.
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    Talk about a major miscommunication!

    . 828passenger 12h ago A woman was engaged/married with a ring on her finger and thought she was meeting someone for a networking HH but the guy thought they were on a date
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    People really can be shameless!

    Fearless-Spread1... . 11h ago Girl was actively on a dating app during the date and I felt like she wasn't being very discreet. A dude once. tipped me $100 to give a drink to a woman at another table and he was there with his wife. Life is wild.
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    Whatever happened to listening and responding like a normal human being?

    Madea_onFire • 12h ago There's always a date where one person continuously talks about themselves non stop the entire time. Like 45 minutes straight of just talking about themselves & never lets the other person speak. It's usually a guy doing this, but I see women do this too sometimes.
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Dating-Relationships dating fails waiters servers askreddit restaurant server life restaurant work tales from your server dating
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