Bartenders Break Down The Worst First Dates They've Ever Witnessed

We all know that not all relationships are meant to make it and that some first dates are going to go horribly, awkwardly wrong.

But that doesn't change just how cringy some of those first date fails are to witness... perhaps especially if you're a bartender.

Redditor gilesvg asked:

"Bartenders of Reddit, what was the worst first date you've ever witnessed?"

Stood Up But No Standing Ovation

"I saw a dude at the theater I used to work at. He was dressed up and had flowers for Valentine’s Day. He sat in the lobby for over an hour and quietly came up to the counter and asked if he could return his tickets."

- IceFireHawk

Hat-Fished

"I was witnessing what seemed like a great first date. So well they started making out at the bar. He had long hair but a five-head instead of a forehead, and bald spot. His hat came off in the heated moment and I saw the look on her face."

"I saw her weeks later and she used the phrase "hat fished" and I'll never forget it. I still feel bad for the dude, he was super nice and paid for everything."

- letsdotacos

Stay Classy, My Friends.

"I was bartending at a causal fine dining seafood restaurant on a Monday night. An older man probably in his mid 60s came to the corner of the bar and asked me for a glass of our 'best red.' I gave him the wine list and he selected the most expensive glass which he could not pronounce."

"He told me he was waiting on someone as he sucks down the glass. He paid for it and continued to wait. About 20 minutes later, he ordered another glass and tabbed out again."

"Roughly an hour after he got to the bar, a woman probably 10 years younger than him showed up. The man turned around and loudly said in a disappointed tone, 'Wow, you don’t look anything like your picture!'"

"She sat down despite his comment and ordered a glass of house Chardonnay. I checked on them occasionally, but neither of them wanted to order food. Every time I tuned into what they were saying, I noticed that only he was talking, and it was mainly about all his surgeries."

"When a bar table freed up behind them, the man looked at me and said, 'We are sitting here, and I am having dinner.' He stood up and sat down before she could even answer."

"When I brought menus over to them, he pointed at something random, and she ordered a small pasta dish. He continued to only talk about himself and showed her pictures of his ex-wife throughout the meal. She barely spoke."

"Toward the end of the meal, he looked at her and said, 'Have another glass of wine!' She declined. He replied with, 'What do you think I’m going to do?! Take advantage of you?' and turned to wink at me."

"She pushed her plate away and asked me for the check. Once the man said he was going to pay, she grabbed her purse and left."

- MotleyCute

Super Awkward

"She and her date seemed to get along okay at the start, but after about half an hour, neither of them seemed to be talking."

"For another half hour, they kinda didn't say much, looking at their phones a lot until the guy literally just got up and left."

"She decided to just take out her laptop and work on some Photoshop project for a while before heading off."

- Cyanide_Revolver

Bring Your Mom On A Date Day

"I've been bartending for 20+ years and have seen A LOT of bad first dates but the one that will always stick out to me was the guy who had his mom vet his date for him."

"He was there at the other end of the bar, but his date had to sit and meet his mom first. They were the only three people in the bar at the time so it was suuuuuper awkward."

"I pretended to watch hockey but I was so intrigued I was eavesdropping the whole time. The poor girl seemed so lovely that she was too polite to just bail out of the situation so she actually did it! I immediately knew something was f**ky when she walked in and got stopped by the mom on her approach to him."

"The guy seemed so comfortable that it clearly was not the first time it happened. So f**king weird."

- dunkan799

Fodder For Some Kind Of Reality TV Episode

"I was a bartender for over a decade. One night, I watched a guy leave the bar to use the bathroom, and the girl he was with (first date) said to me, 'How many times do I have to bring a date here for you to finally hit on me?'"

"I told her I was engaged and had zero interest. The guy was otw back from the bathroom, overheard her say that, and proceeded to lose it on her in front of everyone, which was understandable."

"They both screamed at each other and left the bar, and that was their first date. I have not seen anything worse since."

- lettheexpletivesfly

Worst Date In Under 10 Words

"Her husband showed up and he was P**SED."

- dirtylaundryrecords

A Missed Opportunity To Laugh

"I was working a bar one weekday night. A woman came in, ordered a drink, and sat at the bar. On the opposite end of the bar, a man came in, ordered a drink, and took a seat."

"An hour passed. They were sat in positions that blocked their view of the other. After an hour, I hear the man mutter, 'Ah, f**k this,' and put on his coat to leave. He headed for the exit near where the woman was sitting."

"They spotted each other and realized what happened. Personally, if that happened to me, I'd think it'd be very funny, but these two seemed annoyed with each other, didn't seem to talk a great deal, and parted after about 45 minutes."

"The biggest question of all was, why didn't either text their whereabouts to the other? Hahaha. Surely they had communicated beforehand."

- crumcrumbooty

So Brutal

"I saw a girl and a guy go on a blind date. They've been talking on the phone before to get to know each other and here comes the first date."

"They met at the bar. He was there first waiting and she came in."

"They talked for a minute and he said, 'Oh, let me get the flowers I got you. They're in the car.'"

"He walked out and didn't return. I felt bad for her. You can at least finish the date or have a drink and then gracefully leave."

- Wesmom2021

"To save himself a few seconds of mild embarrassment, he caused his date a serious emotional hurt."

"At least she will eventually realize that she was lucky to be 'missing out' on his company."

- Melenduwir

Not An Attractive Kind of Spicy

"I ordered some hot wings with ghost pepper sauce from a bartender. As he watched me eat the first wing, he told me about the last guy who had ordered them."

"It was a young guy in a suit who was clearly on a first date with the girl he brought along. The guy boldly ordered the ghost pepper wings trying to impress her, took a couple of bites, got up without saying a word, and walked off."

"After 30 minutes or so, the girl realized he wasn’t coming back and angrily got up to leave… but the bartender had to stop her and remind her that she still had to pay for the wings."

- rutsh95

"Eating wings is one of the least sexy or impressive things a man can do. The breathtaking madness of someone who attempts this on a date... And then makes their girl pay for their mistake. Stay single, dude."

- votekoby

Not The Best First Date Experience

"I was a bartender at a restaurant. A 13-year-old boy came in for his first date with a 13-year-old girl. His mom brought them. She planned on getting them seated at the table and then leaving them alone to come to eat at the bar herself."

"The boy would not let her leave. The girl hinted multiple times about the mom leaving. The mom hinted about leaving too. He just ignored them. Finally, the mom says she's leaving to give them some privacy. When she tries to get up, the boy reaches out, grasps her arm, and tells her not to leave."

"They all sat there awkwardly at the table. One of the servers heard the girl in the bathroom on the phone making fun of how weird he was being about not letting his mom leave then."

- esoteric_enigma

"I wonder if he didn't want it to be a date and that's why insisted his Mom stay."

"A friend of mine went through something similar where his parents were trying to set him up with a friend of his. She really liked him and both parents thought he was shy so they kept trying to set them up for dates."

"He didn't like her like that and no one would listen to him so he did his best to make sure they wouldn't be left alone."

- KingPinfanatic

Go, Elaine!

"My own! I bartended a bar in between other things I had going on at the time (25+ years ago). A pretty RN from the local hospital would stop in after her shift, she eventually asked me out."

"On a free weekend (first date), we went to another bar that had a band that night."

"She went full Elaine (from 'Seinfeld') dancing! Like, people got out of her way to let her dance her crazy s**t, which only fed her idea that people thought she was an awesome dancer!"

- AmbientGravy

"So... How many kids do you have now?"

- SparkDarbles

"Ha! I have two, a grown daughter and son. No kids with her. But to be fair to her, at least she wasn’t afraid to have fun, and to have fun assuming there was no judgment."

"I feel awful for judging her enjoyment. Early 20’s me, trying to be cool, thought she was whacky, late 40’s me thinks she was probably genuinely enjoying life better than most."

- AmbientGravy

...Ouch

"Working at a craft beer bar, this guy asked me out right in front of his absolutely STUNNING date and kept winking at me throughout the night. She left, and he did not get my number."

- Sea-Ember

Partying For The Wrong Reasons

"A guy showed up to the bar when it was a touch slow, I got him his first beer and noted he was dressed pretty nicely. Being the chatty guy I am, I asked him if there was a special occasion or something. He said he was waiting for a girl to show up for their first date and was pretty excited."

"The guy hung out a bit at the bar top for a bit before milling around, and then he came back and ordered some onion rings and another beer. Things got a bit busier so I didn't keep close tabs on him, but then an hour or two went by, and I noticed he was still there alone, and he looked a bit confused and saddened."

"I asked him how he was doing, he said she hadn't shown up yet. Because I've been there, I got him a drink on the house and asked if he needed anything else."

"An hour later, the date finally showed up, completely plastered, and they walked up together to sit down and she tried ordering some shots. I know most bartenders in most places won't really stop themselves from over-serving someone, but I told her, 'Perhaps you should slow down a bit; here's a glass of water and a free soda.' She knocked both over and demanded shots. The guy was clearly embarrassed."

"They put in a small food order, and about 30 minutes later, I saw him pouring her into a cab with a to-go container. He came back in and we just chit-chatted when we could for the rest of the night."

"Dan, I really hope you found the right woman for ya."

- hertothesquatch

It's clear why these instances were some of the subReddit's favorite examples of first date fails. From embarrassing to uncomfortable to borderline scary, these potential partners were clearly bullets dodged.