20+ Waiters Talk About the Most Awkward Dates They Witnessed Firsthand

3 years ago

A waiter’s job is much more than serving appetizing dishes and getting tips. Sometimes they can unintentionally overhear some pretty interesting dialogue or watch comical situations. In a Reddit thread, workers from the serving sphere recalled the weirdest and most awkward dates that they had ever witnessed.

We at Bright Side were avidly reading their stories that we think deserve to become the plot of an award-winning movie.

  • A couple was shown to their table, and the guy was on the phone the entire time. While I was putting together the salad, the woman comes out to the lobby and asks to get her meal packed up. She ended up paying her half of the bill and ducking out. She told me this was their first date and she was set up by a soon-to-be-former friend. Said she was going to be calling her friend as she walked out. When I brought the guy’s meal to him, he asked where her dinner was and I told him what happened. He really thought she was in the bathroom... © newguy1787 / Reddit

  • A middle-aged couple:
    Man: [30 min monologue about the cars he likes, how fast they are, what the challenges are in maintenance. He was literally going on non-stop every time I passed them]
    Woman: [taking the sudden silence as her chance to get a word in]
    Woman: Well, I really like butterflies.
    awkward silence
    Guy: [continues his car talk until dessert]
    Curiously enough they came back 2 more times over the summer... © Sweetholymary / Reddit

  • I worked at a higher-end restaurant. My first shift a woman in her 40s or 50s came in with a tall, and handsome guy no older than 30. Nothing wrong with that in my eyes, but all of my interaction with them was the woman talking down to me on some sort of power trip. She ordered ahi tuna, RARE. She sent back 4 separate plates (all too well done) to the absolute horror of her date. After the 4 plates, she sent the last one back and asked for a shrimp cocktail instead. When I brought the check, and when I came back to pick it up, her date was gone, and I don’t mean, went to the bathroom, all of his things were gone and he was nowhere to be seen for 30 minutes. She apologized to me and asked if I could take the ahi tuna (~$45 each) off of her bill. Told her to pound dirt. Not really, but my manager did. The next day she wrote a 500-word review about me, using my first name, on the restaurant’s Facebook page. My boss printed it out, framed it, and I still have it today. © IDKimjusttheintern / Reddit

  • I worked at a bar where like 50% of our business was from Tinder dates. This one time, 2 guys came in separately and sat at different tables by themselves, along the same wall. They were both facing the door and clearly waiting for dates. Eventually, a woman comes in, walks up to the closest guy, sits down and they start chatting. After ~5 minutes, the other guy, who is still waiting by himself, gets up and walks over to the couple. He says, “Hi” to the girl and is like, “Um aren’t you so-and-so? ...I’m so-and-so, we were supposed to be meeting.” She was clearly flustered, lots of awkward laughter, and she gets up and goes with the other guy to the other table. A couple of minutes later the other woman shows up and sits with the first guy, and he tells her all about it. © frankylovee / Reddit

  • I had these 2 people that were there on a first date. After the appetizers, this poor man got diarrhea and was going back and forth to the bathroom all night. There were only a few other people in the restaurant at the time so it was noticeable and they were chuckling every time he got up. I honestly felt so bad for the guy. © RAM_592 / Reddit

  • Not a first date but we did have a guy come into our steakhouse on a Saturday night at 7 PM with NO RESERVATION. He then told us on the spot that he was going to propose to his girlfriend. We had to seat them somewhere awful, it was right next to the bathroom, and when he got down on one knee, looking around nervously, absolutely no one noticed. He and his girlfriend kept waiting for the rest of the restaurant to see them and go quiet, or even clap for them, but not a single person noticed. She said yes, looked disappointed, and they went back to dinner as if nothing happened. They must not have minded too much because they came back for their one-year anniversary, this time he made a reservation lol! © sophiegitt / Reddit

  • I used to work at a sushi restaurant, and there was a girl who would come about once every few weeks with a different guy. Every single time, she’d order a portion of the same dish, which is like a rice-salad-sashimi bowl, and it was GIANT. I’ve only ever seen a handful of people ever finish the entire thing in one sitting. She would finish the whole thing (with CHOPSTICKS) and always ask for a spoon toward the end. It was always fun watching the guys look stunned when she finished. One day she came with this dude that ordered what she did, and when they both finished the bowl, they ordered another and split it. Wish they had ended up together, but she came back with a different guy a couple of weeks later. © themerrypaek / Reddit

  • I worked as a barista at a coffee shop with a dishwashing sink that brought you face to face with whoever was sitting at the coffee bar across from you. For some reason, so many people chose this spot for their first dates, so I would have to wash dishes and pretend I wasn’t literally on the date with them. One time, a person I knew was on their first date with someone and chose that cursed seat across from the dishwashing sink. Because we knew each other, we chatted a little bit and then, as if a partition raised between us, they began their date... but I still had dishes to do... So uncomfortable! © maybemaggot / Reddit

  • Once, as a high school teenager, while waiting tables at a Mexican restaurant chain, 2 people on a first date came in. They seemed unable to converse. It was super awkward. Painful to watch. Well, at one point the woman asked for a refill of her tea. I dutifully went and got the pitcher and came back to fill her glass. While pouring, I literally dropped the entire pitcher, a full gallon, of sweet, sticky tea directly onto her. It went down her shirt. Her skirt. It was everywhere. She was completely and utterly soaked. I apologized profusely. I brought her out like 4,000 napkins. Her date was dumbfounded and probably thinking, “didn’t think this could get worse, but here we are.” Well, she cleaned up the best she could. And they ate their meals. And, magically, they began talking. They started looking at each other like a new couple looks at each other. They laughed. They enjoyed their food. She dried out. They left the restaurant an hour later, with her arm in his. They gave me the biggest tip I had ever gotten. Somehow, my idiotic, high, blunder, turned the worst first date ever into the best first date ever. © AmishTechno / Reddit

  • Just saw one on Valentine’s Day. The date seemed to be going very well, actually, not awkward at all. They talked non-stop, no lulls in conversation, they were laughing, carrying on, and just generally having a good time. In fact, another server and I were laughing about how obnoxiously loud they were. Then I heard the gentleman say “...and obviously, you’re not still married... right? Please tell me you’re not still married,” she said “well, actually...” and then things got VERY uncomfortable. It must not have been a deal-breaker because they stayed at the restaurant another hour until we closed, but they were very quiet for the rest of the night. Hardly spoke to each other at all. © WhatOnceWas396 / Reddit

  • As a bartender, my personal favorite was one where the guy showed up to meet a girl but left with another dude. The 2 people on the date showed up separately, had a cutely awkward first few minutes, and things went business as usual for about the first 30 minutes or so. Then a guy, let’s call him Frank, shows up and happens to sit on the barstool next to the dude on the date. Frank is a bro. Like a bro bro. I’m not totally sure how this happened, but Frank and the date guy start chatting and within minutes are full-blown bro-ing out. The rest of the “date” was largely the girl looking at her phone while the date guy and Frank had the time of their lives. On one hand, I felt bad for her but on the other, I was watching the best friendship form in real-time and it was kind of hard to be mad at that. After finishing her meal the girl said goodbye and got a taxi home. © Thenegativeone10 / Reddit

  • There was a lady in my section who was by herself. She was just waiting. This lady was absolutely gorgeous and dressed to kill. I ended up talking to her a bit since she was obviously bored. She was smart and seemed like she had a good sense of humor. It turned out she was there to meet some guy on a blind date. I was like, “OMG, what kind of a man would leave a woman like this waiting?!” The guy eventually rolled in looking like a crunchy bro and acting as if he was just too cute. Apparently, the woman confronted him about his being late because he actually got on top of the table and asked everyone in the restaurant if they thought she should forgive him or not. Everyone ignored the guy. Then they talked for a bit and then the guy went to the bathroom. I went up to the table and said, “You don’t need to pay for your drinks or anything. If you want to leave, you can just leave.” She said thanks, but she ended up going ahead with the date. They left my section and went somewhere else. Honestly, I wanted her to ditch the guy so bad. © imk / Reddit

  • I used to wait tables at a steakhouse. This guy used to come every weekend, sometimes alone, sometimes with a lady. He skipped a few weeks and came back on a Sunday with a new lady. I get his table and when I see him I greet him, “Hey, long time no see!” The death stare from the woman almost killed us both. They didn’t speak for the rest of the dinner... And I didn’t get a good tip that day. © Boring-Jicama / Reddit

  • I was working at a high-end steakhouse when a couple comes in on a first date. As I’m taking the order, the woman’s phone rings and she answers. Apparently, her close friend just broke up with her boyfriend and is distraught. The woman asks if her friend can join them for dinner. The man says, “of course” and is really gracious about the whole thing. The friend shows up within a few minutes and is a crying, hot mess, and orders more drinks. Afterward, the man excuses himself to the restroom. While he is away, I overhear the friend expressing concern about the menu prices. The first woman then says, “Get whatever you want, I’m not going to ever see this loser again.” So then I catch the man coming out of the bathroom and tell him what I just heard. He says “What do I do?” I tell him he is welcome to leave through the delivery door in the back and I will play dumb for his date. The guy expresses his gratitude and slips me $100 on his way out. The woman becomes increasingly irate as the night goes on and she realizes the man isn’t coming back to buy them food. So she waits until closing time and leaves hungry in a taxi. © kelpat14 / Reddit

  • Restaurant in Canada — a couple comes in. Man has the first-gen iPhone and they haven’t been released in Canada yet. The guy at the next table is so enthralled with the device he won’t stop talking to the iPhone man. Talks so much that his date got up without saying anything, and walked out the door. © ThePalerKing / Reddit

  • Didn’t happen to me, but I was working while the bartender got to experience it. Guy and girl came in, super weird chemistry all night. The guy is obviously trying to impress her by being a huge douche and she looks like she’s just pretending to not hate it so the date will end faster. At the end of the night, she says she’ll take an Uber home and he awkwardly leaves without her. She then waits for the bartender to come back over, orders another cocktail, and asks for his phone number. © BigFuturology / Reddit

  • I waited on a couple who were clearly on a first date, and the lady was clearly not impressed by the guy she was on the date with. The date was over quick enough and the guy paid, leaving me a 5% tip. The next day, the lady came into the restaurant, walked up to me, said, “that was the worst first date I’ve ever been on, and I was mortified when he stiffed you on the tip” and then handed me $20. © Vomiting_Winter / Reddit

  • One day this (very cute) 20-something girl comes in, orders, and cheerfully asks me if we have any board games that are great for 2 people. 30 minutes later, she comes and sadly asks me if we have any games you can play alone. The guy ended up showing up almost 2 hours late, ordered a bit rudely, she paid for him, and they spent less than an hour talking. He wasn’t interested in playing a game and didn’t really seem interested in his date either. I imagine she was excited for her date and thought the board games idea for a first date was cool, but the guy was so rude being late and not showing any interest... just sad. She came back a few times with friends though and was really a nice girl. © Grog_Bear / Reddit

  • I was bartending this New Year’s Eve. A couple sits down, the guy goes to the bathroom and comes out with his ex’s Instagram up asking his date if she thought he was better than the ex’s new boyfriend. The girl tried to give him an out, but he kept doubling down saying things like, “Well I think you’re better than her so why can’t you say it to me.” She was outside at 2 AM in tears waiting for her mom to come to pick her up. Really hard to watch. © 5oclocksunshine/ / Reddit

  • I worked at a burger chain and this couple came in, sat down, and a short conversation seemed to reveal that she was vegan before they awkwardly got up and left. © tebowthecat / Reddit

  • It was mostly awkward because the woman was unbelievably demanding and rude, but only when her date wasn’t around. I came back with their food and offered a completely over-the-top apology with a tearful garnish. The guy looked at her with horror and asked her what happened, then left. © geologyrocks98 / Reddit
  • A lady comes in to get a table, says she’s expecting a man, and gives us a brief description. He shows up about 10 minutes later and she starts saying she knew it, he looks very surprised and scared. I took a drink order and when I get back they are gone. The hostess fills me in that in my absence they had a heated but civil exchange, the man was married to the lady’s cousin, also the lady was married. Apparently, they had been texting for a while before the meeting. Don’t know if they hooked up in the end or just called the whole thing off. © Hazmatt40oz / Reddit

  • I worked in one cafe a few years ago. A lady who was a regular came in outside of her usual teatime. A few minutes later a dude came in and they introduced themselves. He had coffee, she had tea. Her tea had 12 sugars in it. 2 hours later... I think the only time I heard his voice was his introduction. © borkq / Reddit

What was the most awkward date that you witnessed? Or maybe you yourself have been on an awkward date? Please tell us about it in the comments!

Preview photo credit Lemalisa / Shutterstock


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