'I've told you before, I'm not marrying you': 20 Dates that couldn't have been more awkward

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Remy Millisky • Writer and Editor
Aug 27, 2024 11:00 AM EDT

As a waiter or waitress, you're going to spot a few awkward dates during your career. 

Just think about how many times you've been out to eat and you end up overhearing a couple bickering. Sometimes it's an older couple who seem tired of each other's company. Other times, it's a couple on a first date that's going badly. If you as a diner are able to listen in to their conversation, just imagine how much info their waiter can get from eavesdropping! 

The waiters and waitresses of the world gathered to share their stories of the "most awkward couple date you have ever witnessed at work," with more than 12,300 people sharing their stories. One person noted that if your waiter thinks that you and your date are having a fight or seem interesting, they'll tell the other waitstaff about it, too. That way, seeing if table 14 breaks up before the date is over becomes a spectator sport! 

These truly are some awkward stories. As a few waiters shared, people often want to do their proposals at restaurants, and they need the waiter's help to hide the ring in a fancy glass or dessert item. As you can imagine, the success rate of proposals isn't 100%… awkward!

Up next, read about these hilarious pets that have kept their owners giggling. 

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  • 01
    cluic LONDON SHOP
    via Toa Heftiba on Unsplash
  • 02
    Waiters and Waitresses of Reddit, what is the most awkward couple date you have ever witnessed at work?
    via u/StittDownAndListen
  • 03
    [deleted] A girl hit on me in front of her bf when I was serving. The bf walked off after staring her off and the girl awkwardly sat there alone for a while. I asked a 'girl' friend to take over her table, coz it was too awkward.
    via u/[deleted]
  • 04
    AgainstBelief I work at a dinner theatre, and we usually do proposals where we set up a 'random draw' where the 'winner' comes up on the stage to win their prize, and are then surprised by their partner who proposes. It's usually sweet and makes everybody in the room all fuzzy and warm.
    via u/AgainstBelief
  • 05
    This one guy wanted to take it further and requested to perform a song - he brought his own music and everything. We're pretty easy going at this job, so we agree to let him do it. We do the fake draw, the woman comes up on stage infront of a room of 400 people,
    via u/AgainstBelief
  • 06
    and the music starts to play. Apparently this guy was a little nervous, and he compensated by having a few drinks. So what follows is a slurred performance of a song written by this guy, that seemed to focus on how he was sorry for cheating on this woman with her sister and at the end of it, he
    via u/AgainstBelief
  • 07
    gets down on one knee and proposes. Usually this gets a round of applause, encouraging the person to say yes; but not after that trainwreck of a performance. The poor woman was just holding her face the entire time and starts shaking her head and says "No, what's wrong with you?" She storms
    via u/AgainstBelief
  • 08
    off and leaves him and our stage manager on stage to a bunch of murmuring from the audience. The only thing our stage manager can think of to say on mic is "Well, that's that."
    via u/AgainstBelief
  • 09
    The guy ended up staying for the rest of the show and had many more drinks. That was years ago and it still remains one of the cringiest things I've ever seen.
    via u/AgainstBelief
  • 10
    youngandstarving. First date, I would estimate college age. They're eating and the girl says "I'm having a really nice time, but my friend just texted me and asked me if I wanted to hang out, and I said yes, so I actually have to go."
    via u/youngandstarving
  • 11
    CigarJpug Late to the party but I will share my story. Had a couple come in one night and everything seemed to be going fine. We just hired a new sever who was training and I asked her if she had any questions. She was still nervous about greeting tables so I told her she
    via u/CigarJpug
  • 12
    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 KNEW YOU WERE CHEATING ON ME" I
    via u/CigarJpug
  • 13
    Turns out the guy was her bf 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.
    via u/CigarJpug
  • 14
    Corticulture When I was bartending this guy came into the bar on a week night, average looking guy, late twenties. He sat down and asked for a drink and told me he was nervous because it was his first date in 3 years and they had met on tinder. He arrived 20 minutes before her
    via u/Corticulture
  • 15
    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
    via u/Corticulture
  • 16
    "Are you Joe?", the guy replies yes and gets up to properly greet her looking incredibly excited....she says "no thanks..." and just leaves. What a foul creature. Joe(not his real name) and I proceeded to get way too drunk for a Tuesday. Poor average Joe.
    via u/Corticulture
  • 17
    Jps1023 I worked at a fondue place. 1.5-2 hour meal for two people. Four courses, the works. Couple came in and he had pre-arranged with us to present an engagement ring with the chocolate course with melted chocolate on the plate spelling
    via u/Jps1023
  • 18
    "Will you marry me?" Also roses and other embellishments on the plate. Apparently the entire meal she was explaining to him how bad he was at being in a relationship. Too needy, too emotional, somehow also didn't spend enough time with her and wasn't
    via u/Jps1023
  • 19
    connecting with her? It was an hour long breakup speech. We come around the corner with candles lit and the chocolate fondu and the engagement ring on the plate, the table next to them did everything they could to wave us off, I was holding a camera to capture the
    via u/Jps1023
  • 20
    magical moment...which never came. He tried to get his prepared remarks out, but it was so bad we eventually left the dessert at the table and tried to act like nothing had happened. She left before the check came.
    via u/Jps1023
  • 21
    ThereandBack22 I guess you could call this a couple date. 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
    via u/ThereandBack22
  • 22
    papers. I did my best to avoid that side of the bar. I did bring out tissues for the wife who was breaking down. I ended up boxing up the dinner. The guy paid but I do not envy that ride home.
    via u/ThereandBack22
  • 23
    Served a deaf couple having a fight. They went from both of them signing furiously to her crying and signaling to me for a stack of napkins for, I assumed, her tears. She whips out a pen and starts writing paragraph after paragraph angrily. It was awkward because i
    via r/AskReddit
  • 24
    kept having to come back to the table since they ordered multiple courses and he was just eating and signing while she was hunched over the table writing away while crying. When they finally left they tipped me pretty well though so I guess it wasn't too bad?
    via r/AskReddit
  • 25
    kiwikoopa Idk if this counts, but when I was a waitress at Olive Garden, one of my tables was going over their divorce paperwork. When I greeted the table I asked how everyone was and the woman said, "Terrible! We are getting a divorce." Like ☐ do I say to that?
    via u/kiwikoopa
  • 26
    [deleted] In law school I always worked the Sunday morning shift at the restaurant in town and it was always soooo dead but I'd bring homework so it was mostly ok. Every other week, this couple would come in and order G&Ts and nachos and sit for hours talking about
    via u/[deleted]
  • 27
    how attracted they were to each other, their I life, and would joke about sneaking around and what not. I never thought much of it. Until one day, I walked into the dining room from the kitchen and saw the lady had already been seated in a booth facing me. Her
    via u/[deleted]
  • 28
    dude's bald head was across from her, facing away from me. I approached the table, about to ask the love birds if they wanted their usual, when the dude turned around and IT WAS A DIFFERENT DUDE. The
    via u/[deleted]
  • 29
    lady looked at me sheepishly as he mentioned to me it was his WIFE'S birthday and they had never been at my restaurant before Imao.
    via u/[deleted]
  • 30
    LSDnoiseparty Chiming in late, but one comes to mind. I had a mid 40's man with a young and attractive mid 20's woman sitting at the bar. They were engaging in small talk and ordering drinks, nothing out of the ordinary. After possibly 45 mins a lady storms into the bar, and
    via u/LSDnoiseparty
  • 31
    immediately goes up to them. She grabs the man by the shoulder and says "you.. You're a and walks out. The man turned to his perceived date and says "yeah, she does that" and then left the room, leaving his date to sit there, staring blankly into oblivion until she left. Odd.
    via u/LSDnoiseparty
  • 32
    spoooky_spice Not exactly a date- but I served a couple one time who had met up to discuss the terms of their divorce at the fancy-ish restaurant I worked at at the time. They came before the dinner rush so they were pretty much my only table, and every- time I'd check in on
    via u/spoooky_spice
  • 33
    them the wife was extremely angry/tearful and they were bickering about holiday schedules for their daughter/timeshares etc. it wasn't the end of the world but it was extremely awkward to in to change our their forks or refill drinks while they were so emotionally charged.
    via u/spoooky_spice
  • 34
    [deleted] A girl brought two tinder dates and played them off each other game show style. They seemed to be unaware this was what would happen. Splitting the bill was hilarious.
    via u/[deleted]
  • 35
    CMMND Was a bartender/waiter a few years back and I was delivering some food to a table to find out that it was my ex and her new boyfriend sitting at the table. We had only stopped seeing each other a month earlier so it was incredibly awkward for everyone.
    via u/CMMND
  • 36
    Penya23 When I was waitressing in college, I witnessed the single most embarrassing thing to happen to a person to date. Right in the middle of their dinner (and in the middle of our Friday night dinner rush), this poor guy stands up,
    via u/Penya23
  • 37
    taps his wine glass to get everyone's attention, and then proceeds to tell EVERYONE what a fantastic person his gf is, how much he loves her, and how lucky he is to have her in his life. The whole time this is happening, she is just sitting there watching him with the most
    via u/Penya23
  • 38
    boring look on her face. It was so weird. Kind of like, 'Yeah, tell me something I don't know". Then poor guy pulls out a ring, gets on one knee and asks her to marry him. She gives him the most disgusted look imaginable and says "THIS is the ring you expect me to say
    via u/Penya23
  • 39
    yes to? Are you ? Could you be any cheaper?" Then she gets up and walks out, leaving the poor guy just kneeling there. I didn't charge him for the meal. Edit: Just to clarify, this was a real rejection.
    via u/Penya23
  • 40
    Not only had they not even finished their meal when he proposed, a hostess at the restaurant knew the guy personally. Apparently it took him a really long time to get over it.
    via u/Penya23
  • 41
    PrinceLemonade Working at a chili's on Valentine's Day, the girl gave me her number with her boyfriend in the bathroom, I came back and had to deal with her being sweet to him and nice the rest of the dinner. I did not call or text her, just was weird everytime she'd look me in the eyes following.
    via u/PrinceLemonade
  • 42
    [deleted] They sat down and, from the girl's body language, you could tell she was into him. As the date progressed she closed off, then sat pretty much sideways, then was playing on her phone. The body language shift occurred over maybe 1.5 hours. He didn't stop talking the entire time.
    via u/[deleted]
  • 43
    She did give some nods and "uh huh"'s in response; even perked up a few times to contribute. But his monologue never stopped.
    via u/[deleted]
  • 44
    HappyLittleTrees17 There was a couple sitting at the bar together - seemed like it was a first date. Maybe after 30min of them being together I'm in the back rolling silverware and the dude comes running into the back and goes, "there's an exit back here, right?" and proceeds to bolt out of the back door.
    via u/HappyLittleTrees17
  • 45
    We were all flummoxed. The girl sat at the bar alone for at least another 45 minutes before she left.
    via u/HappyLittleTrees17
  • 46
    Durnovarian There's a habit of some older couples where the elderly gentleman will order on behalf of his wife. I guess it might have been cute and romantic once, but it doesn't work with some younger couples. I was serving a younger couple (early 20s), who
    via u/Durnovarian
  • 47
    seemed pretty early into the relationship. They were ordering drinks and he orders her drink for her. Far from being dazzled by him knowing what she wanted, she didn't want any of it "Well I'd actually like a latte, not a coke. But fine whatever, if I don't get a say..."
    via u/Durnovarian
  • 48
    He responded quite angrily with "oh sorry, have what you want then!" She got her latte and he glared at me. They ate and left. Not been in since, I'm sure they're doing well.
    via u/Durnovarian
  • 49
    Lampmonster1 I've told this one here before. I worked in a resort hotel, high end, I waited tables in the fine dining restaurant. It was pretty common for people to propose there, so much so that I had a system for the whole thing. One guy came in and wanted to do the ring. in the champagne thing,
    via u/Lampmonster1
  • 50
    and I talked him into doing a dessert alternative that doesn't result in a sticky ring and champagne on the floor. Anyway, long story short. I bring the ring, she says , I've told you before I'm not marrying you." He flips, she's super
    via u/Lampmonster1
  • 51
    calm about it and basically treats him like a child having a tantrum, which to his credit he was not screaming or anything, just very upset. He left, she ate the dessert, eventually he came back and paid and they left together. Super awkward.
    via u/Lampmonster1
  • 52
    shadez36 Not technically a waiter, but I worked at McDonalds (one of the thankfully less trashy ones) and a couple came in. Woman sat down and the man tried to order. There was lots of umming and ahhhing at what he wanted to buy, he ordered two meals that we gave to him and he went and sat down. What
    via u/shadez36
  • 53
    followed was a 10 minute shouting match about how he wouldn't take her on a 'proper date' and up even a McDonald's date. Guess how he he ordered the wrong thing.
    via u/shadez36

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waiter Awkward marriage proposal dates proposal restaurant couples workplace restaurants waitress socially awkward dating
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