The Worst First Dates Ever

These dates are more than just awkward


First dates are always a bit, awkward, sometimes even terrible. And since firs dates usually take place in restaurants, waiters get to see all the awkward drama unfold. They lists out the worst first dates they have seen on Reddit.

1. The Painfully Slow Date

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 three-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. [_laceyface_]

2. The Pro-Semite

He made a comment to her about how he’s “not jew-y” so she should order whatever she wanted. She was Jewish. Spent the rest of the evening in silence as he went on about how his ex-girlfriend was anorexic and “so annoying about food.” He was happy to be on a date with a woman who could eat like a normal person. [Outoffixins314]

3. The Heartless Date

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. [evaholierhoek]

4. Dude, You’re Dead

Man and woman cozy in a booth. Different woman storms in through the front door literally dragging two kids behind her, right past the hostess station to stand defiantly in front of the couple and proceeds to BITCH. Dude was nailed. [twoliterdietcoke]

5. Worth Being Stood Up For?

Olive Garden, around 2014 or so, from like 7:30 – close on a weeknight.

Middle-aged man of sub average attractiveness was sitting alone at a table with a glass of water, insisting that his date would be “just a few minutes, there’s traffic”. At around 9:15, manager had to come out and let him know that the restaurant would close at 10, and if he’d like to place a food order, he should probably do it now. He ordered a bruschetta appetizer, and said again that his date was on her way and they’d order when she got there.

9:45, this BEAUTIFUL woman walks in and awkwardly stands by his table. I couldn’t hear the conversation they had, but the man then asked for a box for the appetizer and they wound up leaving together without her even sitting down. [danisaurrusrex]

6. Never Give Up

I used to work at a little shi**y diner place, definitely not the type of place to bring a first date. There was this guy who’d come in every Friday with a different girl. He was a very good looking dude and was alway super polite and very nice to me, but he was super awkward. The girls would look kind of skeptical as they walked in (probably because of the crappy diner scene). Every week, about halfway through the meal, like clockwork, the girls would develop these “get me the f**k outta here faces.” That’s when I would bring the check. They always boxed up their food and left right away.

I had the chance to talk to one of them while he was in the restroom. Apparently, he wasn’t harmful, there was just something off about him that the girls didnt like. He’s persistence is on point though. [glutenfree_water]

7. Next Date Please!

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 “SEPERATE”. 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. [oversized_canoe]

8. Sounds Familiar, Girls?

Once witnessed a date where the dude talked about how special he was and how his mind wasn’t like other people’s for the entire date. The girl was politely nodding along and every time she tried to get a word in, he’d cut her off. Absolutely brutal. [frogsmouth]

9. First-World Sympathy

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. [schmackers]

10. The Interrogation

Had an obvious first date where the lady was grilling the guy on how much money he makes and he didn’t really want to answer. It was awkward serving steak and salad during an interrogation lol. [literallynamedchad_]

11. Please Rescue Me!

I work at a fairly nice Italian restaurant, where we do a lot of business. One night a man who I was not even serving came up to me while I was punching an order in on the computer and hands me $20 and a napkin with a phone number on it.

He proceeds to tell me, “I am on the worst date of my life, this woman is hurrendous and I have to get out of here. Take this $20 and please go to the nearest phone and call me and tell me that I have to get home right away. I don’t care what excuse you make up, I just gotta get the hell out of here.”

Initially, I thought he was kidding until two minutes later the guy who was serving him came up to me to tell me how wicked this woman was and how he could tell the guy didn’t wanna be there. I promptly called that guy as soon as I had a free minute.

One of my shining achievements as a server. [XelaKebert]

12. When the Waiter is a True Bro

It was one of my first dates where the waiter definitely could sense the awkwardness. I was a junior in high school. I had been flirting with a senior for a couple months and asked her out the day I got my license. I picked her up from her house and within 1 minute of being in the car she got a phone call. One of her best friends died of a Brain Aneurysm earlier that day.

I told her that we could delay the date and offered to take her home, but she declined and insisted we carry on. We get to the restaurant and she is crying at the table. I didn’t say any words to her other than, “Are you okay?” the whole date because she was either texting her group of friends or couldn’t make out words due to being so hysterical.

The waiter kept coming by and sensed how awkward I was feeling. Out of all my restaurant experiences, I have never received my entrée and check so fast. The waiter was a true bro. [MaybachMusic22]

13. “Talk to each other!”

On our second anniversary, we went to a small dinner at a nicer place. My boyfriend is on his phone trying to find an old picture of our first date. He dug through his phone for like 20 minutes while I sat there and talked to him, when all of a sudden two girls drop a note on our table. It said, “It’s a first date! Talk to each other!” And some other crap like that. Apparently THEY thought out “first date” was awkward and uncomfortable!

Now every time he gets on his phone, even though it’s almost two  years later, I think of that date night. [ugaugarox]