Tonight, many people will go on a date with someone new for the very first time. Why? Because no one wants to be alone on Valentine’s day and everyone wants to have a cute story about how they met on the world’s most romantic holiday to share with their future grandchildren. Sometimes those dates go well, but other times? They go very, very poorly. Fortunately for us, the waiters of Reddit — the people who have to witness dates go so wrong that the cringe is palpable — have banded together to share the very worst dates they’ve ever seen.
Let’s start our trip through “cautionary tale land” (Disney’s working on adding that one to the parks) with this story of a guy who didn’t really care if his date lived or died — literally:
I was working in a small restaurant with two floors. A woman and a man came in and I had a table for them upstairs. It looked like they had a first date because they were asking those “getting to know each other”-questions. After ordering food the woman had to go to the toilet, which is downstairs. As she walked to the stairs, the food arrived. She walked down, tripped and fell all the way down knocking her head on the ground. Two colleagues immediately rushed over to her to see how she was doing. She was unconscious and bleeding from her head so they called an ambulance. I went to the man while he already started eating and told him his partner (didn’t know how to call her) fell down the stairs and that she was unconscious and that an ambulance was on the way. He walked to the stairs, looked down and walked back to his table to finish his food. Later the ambulance arrived and I asked him if he wanted to go with hem to the hospital and he said no while finishing her food as well. It was so awkward he just sat there for another 45 minutes eating, drinking, paid the bill and left. I still don’t know what kind of relationship they had and whether the woman is okay.
Jesus! What about this dude, who had to eat the softest food possible on a first date?
I work in an Italian restaurant. A few years ago I waited on a guy and girl who met for the first time upon arriving at the restaurant. There were awkward pleasantries exchanged at the door and then they were seated.
When I was taking their order the guy asked if we had soup because he had mouth surgery a few days prior and chewing food was still a little rough. We don’t have soup, so I explained that the “softest” food on the menu was gnocchi. He ordered the house gnocchi and proceeded to cut each tiny dumpling into four or more pieces and slowly chew each piece. He ate that entire dish over a 3 hour period and the girl stuck it out for the whole thing. She looked miserable and I’m pretty sure they never saw each other again.
And then there’s this ever-popular chestnut about a guy who loves nothing more than himself and isn’t afraid to let anyone else know it:
Served a couple a few months ago. Everytime I walked over, he would always be the one talking, and she would just be sitting there not having a good time. At the end I asked if it was one bill or separate and she immediately piped up “SEPARATE”. I go and take his payment, and as I hand over the Debit machine to the girl, I see the guy take his phone out and start swiping through tinder.
Or this woman, who decided to be “kind and generous” in the most awful and insensitive way possible:
I was working at a Mexican restaurant at the time. I was waiting on a couple and I could tell it was a first date by the questions I heard them asking each other. Anyway, towards the end of their meal there was this Hispanic girl sweeping next to their table and the woman looks at her, holds out the remains on her plate and says, “would you like to take this home to feed your kids?” I stood there in complete shock. This woman spoke no English, but she could tell this random woman was completely degrading her. The sad thing is she seemed like she really thought she was doing a good deed. Her date looked so embarrassed.
And then there’s this woman, who was so awful that her date had to escape:
Late to the party here but I was bartending in NY and watched this couple that had met on Tinder have their first date sitting at my bar. The girl was a complete maniac. Kept bringing up the fact that the dude she was with could be a psychopath and could murder her (he had given no indication of this) and went on tinder while he was still sitting beside her at the bar. Kept telling him he was lucky that she agreed to meet him at all and she didn’t think he’d be this boring. She ordered about 5 or 6 LITs and several shots, he literally just had 2 beers. She made him pay for everything. My favourite part of this shit show was that he excused himself to go to the bathroom and left through the fire escape. Absolutely brilliant. To be clear, there was only one official entrance and exit. This dude escaped out the back and she went searching for him. Straight up thought he had disapparated out of the bar.
Sometimes, the date is just bad for other people, even when the couple’s having a “pretty good time“:
I work at a Japanese restaurant and one couple comes to mind — it was the “worst” for everyone else involved. we offered “private” rooms that have sliding doors, and this couple clearly was hitting off very well…to the point that after a few drinks, she had moved to his side of the table and they just went at each other’s faces & bodies for about two hours. they could have done all that with the doors closed and it would have been less cringey – still cringey nonetheless – but no, the sliding doors were wide open for all the patrons to see. kids, big groups of people, waitstaff, runners, etc…
if i remember correctly, they tipped pretty bad too, so it was not a fun time.
Hmmmm, maybe Tinder isn’t so great after all:
It was an attractive young woman and an average-looking man. First off, these people were 30 and I have no clue why they decided to go to Applebee’s for dinner.
The guy was wearing plaid sleep pants and a oversized red zip-up Columbia. The woman was dressed more nicely, but it was still casual. All goes well until it comes time for entrées. This guy orders a fuck ton of ribs (a few full racks) and refuses the girl her original order of a house sirlion, which was only about $6, less than a fifth of his order. The man orders a four dollar salad and a water for her. The woman stops talking completely while the man talks about some crazy party he went to. The man guzzles a few Strawberry Quencher Iced teas, says “Seeya Friday, bitch” and leaves her with the bill.
She said the guy seemed nice when they talked on Tinder, but was very uncomfortable with him in real life, and afraid to say something. A co-worker and I paid for her meal, and later she and the same co-worker starting dating, and they are engaged now.
At least that story had a happy ending. But let’s not end on that note. Let’s finish our trip through this gallery of horrors with a story for the ages (meaning it’s both cringey, happy, and a little long, so buckle in):
Ok so I have been a bartender and a waiter over the years and have witnessed a couple of really sad ones, a couple crazy ones, and one that was just brutal. This one was the best of them all, I thought.
Good looking dude, fit, clear shaven, kind of looked like Jim Cantori from the weather channel but younger (24 had to card him) and slimmer. Sitting at the bar going on about how he had a date with this girl that his best friend was crushing on hard. That his friend just refused to ask her out because she was into him instead. He was really getting into his story when she walks in and he clams up like someone shocked him. She was by anyone standards drop damn dead good looking and killing it in a little black dress and high heels. It was really that rip the record kind of moment.
Anyway, she comes up and the do the little kissy huggy greeting and she orders a tequila shot with a lime. He does one with her and they banter about getting that out of the way and move in to a little more intense banter and out of the blue this dude whistles at me. Shocked honestly as the bar is pretty empty. He whistles at me again while I am looking at him trying to figure out if he really just whistled at me like a fucking dog. “yo man, more shots!”.
Disappointed as he really kind of seemed like a nice guy I go to pour him a shot and let him know I am not a dog he does not need to whistle to get a drink. “Sure sure man..no worries just keep and eye out we are gonna get lit! Yo!”.
I retire to the side bar real quick and one of the other guys working that night starts to talk to him while the girl goes to ladies room. When she gets back he whistles at the other bartender again and shouts “Hey man! Where are my shots! Pronto!”. This guys starts just hammering shots. Not crazy but pretty damn quick he is though at least five. Girl only did the one and is sitting there sipping at a Wine.
The dude, we will now call “YO!” starts to get a bit sideways. Nothing big, just loud, laughing at his own jokes, talking over the girl every chance he gets. He then announces that he has to piss on a rock and walks to the back. The girl looks mortified and sad. She is texting away like a mad man. Then I hear him in the back raising some cane and out he comes with a dude under his arm. They sit down and he starts talking to different girl at the bar. He is not really piss drunk but well on his way and says something out loud to the other girl about gay people and walks outside. His friend follows quickly after and the girl is left at the bar alone.
Five minuets later the friend walks in, sits down, has a drink with the girl. I hear him say that he put him in a uber and sent him home. They walk to go to the place the other dude had reservations for them at. I honestly thought hell ya, good for you dude.
About 30 minutes later YO boy walks back in sober as the day he is born! Sits down waves me over and apologizes for whistling at me. Give us 20 bucks and buys us a shift drink for when we get off. I was off at this point and sit down to have mine with him. He lets me in on his game.
He did it all for his friend. Got 1/2 drunk played the fools and called him to come save the day. Honestly said “he is a better man for her than me. She is really just not my type”. I was stuck between awe and impressed.
They all came in about a month later looked all buddy buddy the trio of them. That asshole whistled at me again but I admit it was funny.
Stay safe out there!
(H/T: BroBible)