Let’s be honest, dating can be downright exhausting. So when I stumbled upon this Reddit thread where food service workers spilled the tea on the most painfully awkward dates they’ve ever witnessed, I knew I had to share. Grab a drink, get comfortable, and get ready to wince…
1.
“I was serving a couple, probably in their mid-twenties. It was Valentine’s Day, and they were arguing a lot (probably because it was a chicken wing place and Valentine’s Day). The guy ended up calling me over to the table to calmly ask me, in front of his date, ‘Do you have a high chair or a booster seat since someone wants to act like a damn child.’ I was speechless; she wasn’t. They left soon after that.”
2.
“I was serving a mid-twenties-aged couple on a first date. When it was time to pay, the guy asked for separate checks, and the girl looked surprised. He pulls out his card and pays, then goes to the washroom. I run the girl’s card (she already looks nervous), and it got declined. We try again, but it is declined again. I asked her if she needed a moment to figure it out (check her online banking or w/e) and she said yes. The guy comes back, and I run her card again. It got declined again, and the guy sits there stone-faced. I walked away again, and when I came back, the guy ended up paying for it. He wasn’t thrilled. It was super awkward for all of us.”
3.
“I bartended at this restaurant that was a hotbed for match.com/eHarmony/OurTime first dates. Our clientele was usually in their 40s and 50s, and so were our first daters. They were always entertaining, some even ending in the parking lot for some extracurriculars. However, one stands out above all else. The couple meets and they begin talking. I got a weird vibe from the woman for most of the evening, but it was a busy Saturday night and I didn’t have time to pay too much attention. Hours went by, and as business died down, I overheard what had to be the interaction of the night. Guy: ‘Well, this is my first time doing this online thing. I think it’s going pretty well!’ Woman: ‘Oh… oh god, no. No, it’s not going well. You look nothing like your picture, and this conversation didn’t just make up for that. I’m going to do one more so I can justify coming out here while you settle up with the bartender…'”
4.
“Not a waiter, but I was working as a supervisor in a restaurant. There was a couple that came to lunch every day and, every day, they went to the bathroom together for like 20 to 30 minutes, so we all assumed they were having sex. It was inappropriate, but there was nothing we could do. Then, one day the woman came to the restaurant with another man. That man was her husband, which made for a pretty awkward moment.”
5.
“This woman arrived before her date and was sitting alone in the booth waiting. She had a kind of generally angry air about her. She ordered a glass of wine and sat there drinking it. By the time the guy arrived, she had finished it. I asked her if she’d like another glass, and she said, with a scowl on her face, ‘I don’t know. It depends on whether or not he’s paying.’ The guy looked kind of embarrassed and said sheepishly, ‘Uh, yeah, I’m paying…'”
6.
“One of my coworkers walked in on a guy getting a blowjob under the table.”
7.
“A couple came into the restaurant dressed very goth. I wasn’t their server but I was running the cash register just a few feet away. They proclaimed to everyone that they were energy vampires but not to fear them because they wouldn’t hurt us. They said they didn’t need our food for sustenance, but enjoyed the taste. After ordering the meal, they politely asked the waitress if she would stick around for a second so they could feed off of her aura and have enough energy for the night. The waitress said yes… The couple clasped each other’s hands, closed their eyes, and made sucking sounds for a solid minute before leaning back in the seats and sighing as if they had just had a turkey dinner. The waitress was tipped well for her delicious energy.”
8.
“I waited tables at Olive Garden 10 years ago. A guy and his wife sat down at a table and immediately started arguing. Something about his affair and how a baby from it was costing them money. Finally it culminated as I was bringing out their salad. As I walked away I heard the wife say, ‘Well, maybe if you hadn’t boned our son’s girlfriend and gotten her pregnant, we could afford to eat somewhere nicer than Olive Garden. Oh look, the highlight of my meals, UNLIMITED. BAGGED. SALAD. Maybe you could save up and we can go to Joe’s Crab Shack for our anniversary, asshole.'”
9.
“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 papers. I did my best to avoid that side of the bar, but I did bring out tissues for the wife, who was breaking down. I ended up boxing up their dinner. The guy paid, but I do not envy that ride home.”
10.
“I had a couple come in one night and everything seemed to be going fine. We just hired a new server who was training. She was still nervous about greeting tables so I told her she could shadow me and watch what I do. We go over to the couple’s table and all I hear from the new server is, ‘YOU FUCKING BITCH I KNEW YOU WERE CHEATING ON ME!’ Turns out the guy was her boyfriend 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.”
11.
“When I was waitressing in college, I witnessed the single most embarrassing thing to happen to a person. Right in the middle of their dinner (and in the middle of our Friday night dinner rush) this poor guy stood up, tapped his wine glass to get EVERYONE’S attention, and then proceeded to tell EVERYONE what a fantastic person his girlfriend was. The whole time this is happening, she was just sitting there with the most bored look on her face. Then the poor guy pulled out a ring, got on one knee and asked her to marry him. She gave him the most disgusted look imaginable and said, ‘THIS is the ring you expect me to say yes to? Could you be any cheaper?’ She got up and walked out, leaving the poor guy just kneeling there. I didn’t charge him for the meal.”
12.
“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.”
13.
“This couple sat down and, from the girl’s body language, you could tell she was into him. As the date progressed she closed off, sat pretty much sideways, and played on her phone. The body language shift occurred over maybe one and a half hours. He didn’t stop talking the entire time. She did give some nods and ‘uh huhs’ in response — she even perked up a few times to contribute…but his monologue never stopped.”
14.
“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, 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 “Dammit, I’ve told you before I’m not marrying you.” He flips, she’s super 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 fucking dessert, eventually he came back and paid and they left together. Super awkward.”
15.
“There was a couple at my work having drinks, girl went to the toilet, came back, and admitted that she’d been sleeping with the guy’s brother. Apparently, glasses were thrown across the room and they both got kicked out.”
16.
“There was a couple sitting at the bar together, it seemed like it was a first date. I was in the back rolling silverware and, after about 30 minutes of them sitting together, the dude came running into the back and asked, ‘There’s an exit back here, right?’ He then proceeded to bolt out of the back door. We were all flummoxed. The girl sat at the bar alone for AT LEAST another 45 minutes before she left.”
Have you ever witnessed or been on a really terrible date that tops these?! Share your horror story in the comments, and you could be featured in a follow-up post!
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