Skip To Content

    Servers Are Sharing The Worst First Dates They've Seen, And I've Never Felt More Secondhand Embarrassment In My Life

    They all deserve a raise.

    Many of us have been on awkward, uncomfortable, or just plain terrible first dates, but could you imagine the extreme secondhand embarrassment of being the server at the restaurant in that situation?

    Golden Globes / Via giphy.com

    Recently, redditor u/Flavor_Town_ asked, "Waiters/waitresses of Reddit, what’s the most awkward first date you had to witness first hand?" Here are some of the most jaw-dropping responses.

    1. "I worked at a pub connected to a brewery. A dude came in with a woman. The whole time, they were sitting at the end of the bar, and you could hear the guy talking about how he had a room for them at the hotel downtown. Later, they decided to go to the brewery next door, thinking they were going to pull a little dine and dash. They got over there and didn’t realize we were on the same system, so he ordered a couple of beers. The bartender on the brewery side asked if he wanted to add it to his tab. He looked over, confused, and said, 'What tab? I’ve never been here.' She printed off the restaurant bill plus his brewery tab, and it was like $80. He just blankly stared at the poor bartender, then flew off the handle. The girl he was with ended up paying for it.

    Giphy / Via giphy.com

    "They walked across the street and to the hotel. He'd already invited her up, but she stalled until her Uber got there and then just dipped out."

    u/stocky_stegasaurus

    2. "One of my old coworkers would bring all his first dates to the fancy restaurant we worked at because he would always get his meals discounted. This got tricky when he started dating one of the other servers. Watching her serve a handful of his first dates over the first few weeks of their relationship was always an interesting time."

    Showtime / Via giphy.com

    3. "A guy walked up to our host stand and told our host he needed a table for two. He came alone, as if he wanted to get there early and scope it out. As he sat there waiting, one of my coworkers came up to me and said, 'Isn't that the guy from Burbank?' This guy had been known to meet up with women online, take them to a nice restaurant, run up the bill, and then bounce out of there, leaving these women (sometimes in tears) with a hefty bill. We had industry friends in Burbank who saw it happen in their restaurant and told us. He was so legendary, people made a Facebook group about him, complete with pictures and his name. We grabbed my manager (who used to work as a bouncer) and explained the situation. We showed him the Facebook page and made the decision to boot him. My manager walked over, put his hands flat on the table, and said to the guy, 'We know who you are and why you're here. This isn't happening today. You're leaving.'

    CBS / Via giphy.com

    "The guy looked stunned. Playing dumb, he said, 'I'm a customer. I'm here to give you business, and you're gonna kick me out?' My manager threatened to call the police. The guy left. You'd think that'd be a wake-up call for him, but he kept doing this shit until finally getting arrested. I think the DA charged him with multiple counts of fraud."

    u/Barkusmarcus

    4. "Two 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 came in, walked up to the closest guy, and sat down. After about five minutes, the other guy, who was still waiting by himself, got up and walked over to the couple. He said, 'Aren’t you so-and-so? I’m so-and-so. We were supposed to be meeting.' She was clearly flustered. After lots of awkward laughter, she got up and went with the other guy to the other table.

    Bounce / Via giphy.com

    "A couple of minutes later, the other woman showed up and sat with first guy, and he told her all about it."

    u/frankylovee

    5. "When I was working on Valentine's Day, a couple walked in. She was dressed to the nines, like she was ready to hit up a club. He was dressed more casually, in jeans and a button-down. He ordered his meal, and she flippantly ordered something (seafood enchiladas) without really looking at the menu. Later, he seemed to be enjoying his food, but his date looked disgusted and was flicking bits of her dinner around the table/floor. I walked over to check in and see if she maybe wanted to order something else. I got to the table to ask how everything was, and she got up, SCREAMED that her food was DISGUSTING, and went OFF about how shitty this date was.

    Pop TV / Via giphy.com

    "She started yelling at him about how he should have ordered for her, how dare he take her to such a low-class place, she was so done with this, blah blah blah. She shoved her plate away and stormed out of the restaurant. I told him I'd be right back with the bill and asked if he'd like his food boxed up. This guy shook his head, pulled her plate toward him, and said he was fine with continuing to eat the meals he paid for."

    u/TheTrickyLettuce

    6. "A lady came in to get a table, said she was expecting a man, and gave us a brief description. He showed up about 10 minutes later, and she started saying she 'knew it.' He looked very surprised and scared. I took a drink order, and when I get back, they were gone. The host filled me in that, in my absence, they had a heated but civil exchange. The man was married to the lady's cousin, and the lady was also married to someone else. Apparently, they had been texting for a while after meeting via Craigslist personals."

    NBC / Via giphy.com

    7. "I was a server for a girl who was waiting on her Tinder date, who turned out to be my ex. We had not ended on good terms. It was a rough breakup. He had basically attacked me, and I ran out of the house and locked myself in my car, which he stood behind, not letting me leave, beating on my car until the neighbors called the cops. Then he started stalking and harassing me. I had gotten a new job, changed my number, and deleted social media. I had managed to avoid him for months until now. The look on his face when he spotted me still gives me chills to this day. He played it pretty cool, and I do believe the shock was genuine, but it was as if he had spotted a deer he had been tracking for weeks. I gave the table away, and their date seemed to go well.

    NBC / Via giphy.com

    "I was hoping he had moved past me. Nope. He started 'hanging out' at the bar at that restaurant almost every night, trying to get my attention. He was eventually banned after he got too drunk one night, and I got a job somewhere else."

    u/Stayinschool-tty

    8. "After appetizers, two of the most expensive entrées, a high-priced bottle of wine, and dessert with a bottle of Dom, the man said to me, in front of his date, 'We're on a first date. What more can I do to guarantee I get laid tonight?' The young lady turned deep red, and her jaw dropped open. I sat down the bill and said, 'After asking me that? There is nothing you can do.'"

    Fox / Via giphy.com

    9. "This guy came in and sat down at a table alone, and he kept checking his watch. After about 20 minutes of him waiting (and checking his watch every five), I wandered over and asked if he'd like to look at a food menu. Another 30 minutes passed, and my high-strung hopeful was still alone. On his last swig of beer, a cute-looking girl walked in, eyeing the room, obviously looking for someone. He started to stand, grinning from ear to ear. I looked over to the girl after seeing my hopeful's eyes light up, and she had a disgusted look on her face. The entire date felt forced; every time I went to check on them, she was ordering another drink, and he was doing his best to try to pull conversation from this girl, who had her face in her phone the entire time. About an hour later, I watched the girl get up with her purse and wander away toward the restrooms. She never came back. He footed her tab — $90 worth of drinks, and his two beers were $8.

    BBC / Via giphy.com

    "He continued to come back as a regular, and I became his wingwoman. I eventually set up Mr. Hopeful with Ms. Lonely Heart. They're still together."

    u/l34u05

    10. "The guy's card declined. I didn’t want to embarrass him, so I waved him over near the credit card machine so it would look as if he needed to go to the bathroom. He told me to try it again, and I assumed he was going to move money over on his app. He went back to his date. The card declined again. The machine printed a receipt that stated the reason for decline was 'insufficient funds.' I tried four more times. I went over to the table and said, 'I’m having an issue with the card. It might be our machine; do you have another?' I walked away with the new card, and it declined. I waved him over. He got up angrily, and I’m guessing now the date has caught on. He proceeded to berate me, saying that it must be our machines because HE KNOWS HE HAS MONEY! He started making fun of me and questioning if I knew what I was doing.

    NBC / Via giphy.com

    "He was doing this in front of his date, I’m guessing to save face. He gave me another card — declined. The date paid."

    u/justacomment12

    11. "After the appetizers, this poor man got the runs 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."

    Fox / Via giphy.com

    12. "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 got his table, and when I saw him, I said, '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."

    NBC / Via giphy.com

    13. "The guy showed up to meet a girl but left with another dude. The two people on the date showed up separately and had a cutely awkward first few minutes. Then a guy — let’s call him Frank — happened to sit at the barstool next to the dude on the date. Frank was a bro. I’m not totally sure how this happened, but Frank and the date guy started chatting, and within minutes, they were [acting like old friends]. The rest of the 'date' was largely the girl looking at her phone while her date and Frank had the time of their lives. On one hand, I felt bad for her, but on the other, I was watching a best friendship form in real time.

    Nickelodeon / Via giphy.com

    "After finishing her meal, the girl said goodbye and got an Uber home, but date guy could not have been less fazed. He and Frank hung out, drinking together until closing time, and they helped hold each other up on the walk/stumble out the door."

    u/Thenegativeone10

    14. "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 that she was there to meet some guy on a blind date. He eventually rolled in, acting as if he was just too cute. Apparently the woman confronted him about 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. 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."

    Giphy / Via giphy.com

    u/imk

    15. "At a restaurant in Canada, a couple came in from the USA. The man had a first-generation iPhone, which hadn't even been released in Canada yet. The guy at the next table was so enthralled with the device that he wouldn't stop talking to the iPhone man. They talked so much that his date got up without saying anything and walked out the door."

    Atlantic Records / Via giphy.com

    16. "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 that 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..."

    Bounce / Via giphy.com

    17. "When I first started bartending, I had a woman who was very obviously stood up. She got there, ordered a drink, and would look around every once in a while. I saw her use her phone a couple of times, and her mood just got sadder, until she finally put her phone upside-down on the bar and ordered food an hour later. I wiped what I could off her bill, then paid the rest myself, telling her it was on the house.

    Nickelodeon / Via giphy.com

    "In my career it's happened two more times. I did the same thing. Nothing sucks more than eating alone and defeated."

    u/fraxiiinus

    18. "We had a regular who would always sit in one particular server's section every time he came in. He was always by himself, and he would flirt with her constantly. She was fine with it because he was pretty harmless, always came at lunch, and tipped well. One day he came in at dinnertime with a girl, and they were both dressed up, so it was pretty clearly a date. He still sat in that server's section, and it kind of seemed as if maybe he was trying to make her jealous. They even bought their own bottle of wine. At some point, the date ditched him. Then he decided to drink the bottle of wine himself. The bar served him one more drink because they didn’t see how drunk he was and then had to cut him off when he fell twice. Then he started sobbing to the waitress about how lonely he was.

    MTV / Via giphy.com

    "We ended up calling a cab for him."

    u/garlic_ naaaannn

    19. "A young, in shape, really handsome dude from Spain would be in three or four times a week with a new older woman. The women would buy him everything and basically swoon over him. He’d always walk up to pay with a little smirk, while she would be paying for everything.

    ABC / Via giphy.com

    "He did this for years."

    u/HCkc1n

    20. "My first shift, a woman in her forties or fifties came in with a tall, dark, and handsome guy who was no older than 30. The woman talked down to me and ordered everything for her date. She ordered ahi tuna RARE. She was very insistent on the rare, so much so that I put 'blue rare' into the computer so that everything would be fine. She sent back four separate plates (all too well done), to the absolute horror of her date. I informed her after the second that they wouldn't be taken off her bill, and she scoffed and made some comment about how she's loaded. After the four plates, she sent the last one back and asked for a shrimp cocktail instead. When I came back to pick up the check, her date was gone. She apologized to me and asked if I could take the ahi tuna (about $45 each) off her bill. I told her to pound dirt.

    Atlantic Records / Via giphy.com

    "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 and framed it. I still have it today."

    u/IDKimjusttheintern

    21. "I watched a girl in my college class on a first date with a sugar daddy. They seemed to have a great time, but it was hilariously awkward when she pretended not to know me!"

    NBC / Via giphy.com

    22. "When I was a teenager waiting tables, a first date came in. They seemed unable to converse. It was painful to watch. 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 and her skirt. It was everywhere. She was completely and utterly soaked. My newly blossoming career as a server flashed before my incredibly stoned eyes. I apologized profusely. I brought her out like 4,000 napkins. She cleaned up the best she could, and they ate their meals. Magically, they began talking. They started looking at each other the way 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.

    NBC / Via giphy.com

    "Somehow, my high blunder turned the worst first date ever into the best first date ever. I like to imagine them now as happily married parents of seven lovely children who love telling the story of the clumsy server who poured an entire gallon of tea on her 25 years ago."

    u/AmishTechno

    Note: Some responses have been edited for length and/or clarity.

    BuzzFeed Daily

    Keep up with the latest daily buzz with the BuzzFeed Daily newsletter!

    Newsletter signup form