Worst Dates: People Share Bad First Date Stories

By Annie N. in Relationships On 11th August 2022
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How not to be a gentleman in 2 steps or less

"The guy insisted on paying for everything, wouldn't let me pay my half.

At the end of the date he raged out when I wouldn't stay the night, saying "You women are all the same, you want us to pay for everything, but never give anything in return."

Never called him again."

This nightmare scenario when a stranger decides to hop in to your date

"Had set up a blind date and I was running a bit late. Anyhow, when I got there the girl I was supposed to meet, according to what she was wearing and how she was looking, was having dinner with another guy. I went up to her and asked if she was the one I was supposed to meet and it was, however she had asked this guy who had walked in alone to the restaurant if HE was the one she was supposed to meet and he had said yes, and it was so incredibly awkward that I didn't know what to do."

"I said something like "yeah... so.. what the fuck?" and then he said he was sorry, he just saw an opportunity and took it, he then stood up and left. I don't remember the exact details since it was years ago but I remember it beeing extremely awkward."

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All my homies hate Richard

"14 years old. Guy invited me to a movie. We'd met in person a few times through mutual friends and we talked via FB for a few months before he asked me to be his girlfriend. I of course said yes cause he was cute and I was 14. So I get to the theater and find that he's brought his best friend along. I thought oh well, I kinda feel bad for him cause he'll get third wheeled, but it was his choice to come.

Guy didn't pay for my movie or drinks, but paid for his friends, not that I wanted him to, but I expected him to offer! After all he had invited me... Gotta love that.

Through the whole movie I was the one being third wheeled. Until of course he asked me if I wanted to kiss. I said sure. And so we made out for like half of the movie. He tried to go further, but I was like nah man.

"broke up" with me a week later. Broke my 14 year old heart.

Fuck you Richard."

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Assigned gay at reception desk

"I was staying at this hotel for a prolonged period of time for work in a place where I had no friends. So I ended up chatting with the front desk guys a lot and getting to know them a bit. This was in Costa Rica, so it was good to practice my Spanish too! One afternoon, one of the guys phoned my room asking if I wanted to hit up a movie theater later. I figured the front desk crew (they were all friends and half of them lived at the hotel) was heading to the movies in a group, which sounded like fun after having no social life for a month and a half.

It turns out it was a (super awkward) gay date with one guy. I'm not even gay... He kissed me on the cheek when we got back. Man... So awkward..."

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Any date with Seth Rogen involved is either fantastic or horrible. No in-between

"A close friend of mine had just introduced me to her absolutely gorgeous cousin and I was smitten. As you can imagine, I was really excited when she told me the next day before class (this was middle school, I was ~13 at the time) he liked me too. Being that we were so young, our "date" just consisted of going to the movies. What a better movie for a first date than a comedy! Right? So we go into the theater, too nervous to even hold hands because we barely knew each other and we really liked each other, and sat down for our hilarious dating experience. The year was 2007, the movie was Knocked Up, and it was the most awkward thing I have ever had to sit through."

She decided she'd rather be unconscious than on a date

"Waitress: Sir, I think you should know your date is passed out in the ladies room.

Me: Check please, and can you ask the kitchen to box up our entrees to go?

While I was drinking a glass of burgundy, she had two double Captain Morgans."

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Talk about a missed connection

"I invited a girl I'd just met to go to the summer movies HBO used to show for free in Bryant Park in NYC. We met early and ate some fast food while the park filled up and it got dark enough for the movie to start. Just as it was about to, she said she had to go to the bathroom, and never came back.

I sat through Stalag 17, getting more and more pissed off at being stood up, piling insults on this girl in my head. After the movie, I checked my messages, and she'd left a couple, saying that she couldn't find our blanket again, and then one saying she was going home.

Five years later (FIVE YEARS) it occurred to me that, rather than sitting on my ass fuming, it might have been gentlemanly for me to go and look for her..."

The Frozen saga that went on for far too long. Perhaps...he should let it go?

"Met a guy online, he seemed cool so we decided to go get drinks one night. We're sitting at this bar, the conversation isn't really going anywhere, when he suddenly gets this excited look on his face. He says he has a super important question to ask me, and everyone always answers the same way, so he's hoping my answer will be different. I start thinking that this might be good, maybe it will be a great thought provoking question...And then bam..."Have you seen Frozen?" WTF. I say no, I'm not really into kids movied. He says oh yeah me either, not really interested in seeing it at all. Then he asks the bartneder the same question. Also hasn't seen it."

The guy is supper dissapointed, why is everyone talking about how good it is if no one has seen it. Then we're leaving and I'm trying to make my escape, but as I'm walking away he's like "Wait, do you want to come over to my place, I downloaded Frozen on my laptop, we can watch it together..." My only thought was, who the fuck downloads a movie and doesn't watch it? No thanks buddy. At 27, I figured he could have had a smoother line to get a woman back to his place other than a childrens movie...one that I hate to this day thanks to this guy. After I left, I changed his name in my phone to "Frozen" just so I know not to answer when he calls or texts.

Crack. Not even once.

Met a guy at a club and we seemed to hit it off. He called me a couple of days later to schedule a date. While at the restaurant all of his conversations were drug related (Do you like___? Have you ever done ___?). As he's driving me home he stops in the worst part of town to buy crack. I never spoke to him again.

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The fail heard around the world.

I took a girl to see The Fault in our stars on our first date. I didn't read the book so I didn't know it had a really sad ending, but the worst part is, her mother had died of cancer just 4 months beforehand. I felt like an idiot. Surprisingly we dated for 3 months but did nothing more because we go to college in different states.

TL;DR I took a girl to The fault in our Stars 4 months after her mom died of cancer.

The favor that turned into a nightmare.

I went out on a date with a guy I wasn't interested in as a favor to his friend (in retrospect, never again favors like that!)

During the date he talked about how many friends he has who have rape charges against them, and how unfair it is towards the guys. Great first date conversation, right? He never asked anything about me. Then he proceeded to tell me that he was going to learn the language that my parents speak as soon as possible so he could communicate with them in future. Once again, this was a first date! He was talking about them like they are his future parents in law. Then he told me he'd spent pretty much the entire time since getting to know me lying in bed, thinking about how to impress European women since I'm European. He had literally googled "How to impress European women" and proceeded to list off all the tips he had learned, which definitely didn't apply to me since I never even grew up in Europe!

Best to stay away from the likes of him

On the way home he tried to kiss me, but I told him I didn't want to. Then he tried a second time! After that I wasn't surprised at all about why he has so many friends with rape charges against them.

After the date I thanked him for the date, but said that I wasn't interested in him. The next couple of weeks he sent me so many snapchats of himself lying in bed with texts like "missing you" etc.