Dating Disasters: Weird First Date Stories That Are Stranger Than Fiction

Let’s face it; dating is tough! If the jangled nerves and sweaty palms don’t get you, then the awkward conversation — or worse, awkward silence! — is sure to make it a long evening.

Read some of this creepy, funny, horrifying, and downright weird first date stories, though, and you’re bound to feel pretty grateful if the worst you’ve experienced is a few butterflies in the stomach!

Weird First Date Stories That Will Make You Cringe!

One of the best parts about using an online dating service? Everyone there has the same fears of ending up on a truly terrible first date! So it’s pretty easy to take things slow and get to know each other at least a little bit before you meet up in the real world.

He Was a Great Catch!

“My first date ever was when I was 14. My family was summering at a small lake in upstate New York. The cabin next to ours was rented by a family with a 14-year-old girl, and her mom invited me over to fish from their dock.

The girl had never fished before. She put the worm on the hook herself, which was cool, but then she flung her fishing rod backwards before casting it out into the water. I was behind her.

The hook of her line got embedded in my cheek. My parents rushed me to the ER, but I still have a scar on my face.” — Ned, 29, Hackensack, NJ

The Puppet Master

“He arrived at the restaurant with a small suitcase. Turns out he had brought his ‘puppet friends.’ I was introduced to every single one of them — there were about eight or ten, I think.

He proceeded to use the puppets, and only the puppets, to talk to me. When it became clear that he was not going to communicate at all sans puppet, I excused myself to use the ladies’ room and fled!

Felt a little guilty about ghosting, but I just couldn’t deal.” — Samantha, 33, Portland, OR

Beware the Recently Bereaved

“We had been messaging for a couple of weeks, then a few days before the first IRL date, he wrote to tell me his brother had just died unexpectedly, but that he still wanted to go through with the date. I was wary, but he eventually talked me into it.

Horrible idea!

He was so morose all night that he couldn’t even carry on a conversation. Either he was talking about his brother, or we were sitting in awkward silence.

At one point he went outside to smoke a cigarette, and the guy sitting next to me at the bar struck up a conversation. We got laughing, then he passed me his number on the sly when he left.

I called him the next day, and a week later we began dating. He is now my husband of three years! Oh, and P.S., yes, I let the bereaved brother down easy.” — Jeanette, 26, Tacoma, WA

One Rich Guy Who Wasn’t Worth It

“I was almost ready to give up on online dating but decided to give it one last try after getting a wink from this pretty handsome guy. He also implied that he had a lot of money and ultimately wanted a traveling companion to do things like go heli-skiing in the Alps or spend weeks at 5-star luxury beach resorts.

I was really broke at the time, so I figured what the heck, maybe I’d at least get some fancy meals out of it. For our first date, we did meet at a really expensive restaurant.

But it went downhill the minute he walked in the door. He had five — FIVE! — cellphones clipped to his belt. Like, really? You can’t leave four of those at home for a couple of hours? What do you even need five separate phones for anyway?

He also referred to me by name as often as possible, like he’d taken some kind of knock-off Dale Carnegie ‘How to Win Friends and Influence People’-type seminar: ‘Well, Andrew, let me tell you a bit about myself. When I was growing up, Andrew…’

The only time he didn’t pointedly use my name was when he ordered my meal for me: ‘The gentleman will have the filet, medium.’ At least he had asked me what I wanted instead of just choosing for me!

I got out of there as quickly as I could and have laughed about it ever since.” — Andrew, 44, Rochester, NY

Mamma, Mia!

“He spent the evening showing me photos of himself and his mom on their vacations.” — Mia, 21, Nashville, TN

The Very Sisterly Sorority Sister

“A new coworker, finding out that I was single, decided to set me up with her old sorority sister. This was before social media or even googling people, so it was a true blind date.

I didn’t even see a picture of the woman beforehand. All I knew was that her name was Jennifer, which is a really common name.

Well, it turned out that my coworker’s sorority sister was my real sister! We all had a good laugh about it.” — Topher, 28, Detroit, MI

A Series of Truly Unfortunate Events

“This happened to a friend of a friend in college, who went out with this guy named Steve from her biology class. They went to a couple of bars and had a few drinks at each. But either she had been pregaming, or was on some kind of drug too, or maybe was just a lightweight. Because she apparently got wasted. Really wasted, as you’ll see.

So they go back to his place to fool around, and they’re in his bed. Suddenly this girl announces she has to pee and leaves the room. She wanders drunkenly around for a few minutes and can’t find the bathroom. She’s that messed up! But eventually she ends up in the living room, where she spots this big, tall, potted plant.

Now, peeing into the potted plant would be bad enough, but for some reason (tequila) she decides to move the potted plant, pee on the floor of the living room, and then move the plant back to cover it up!

Pretty horrifying, right? Wait. It gets worse. She stumbles back toward the bedroom, climbs into the king-size bed, and says “Holy s***, you’re not gonna believe this. I am so drunk I just peed on your living room floor.”

And the next thing she knows some woman is yelling, “WHAT?! WHO ARE YOU? GET OUT OF OUR BED! STEVEN, GET THIS DRUNKEN SLUT OUT OF HERE!”

The guy lived with his parents, and she had climbed into their bed.

Wait. It gets even worse! So despite being chased out of the house half-dressed by these irate parents, she still had the guts to go back the next day and knock on the door.

Not to apologize to Steve’s parents, mind you. But to ask if they could give her bra back, which had gotten lost in the shuffle the night before. It was her ‘favorite bra.’” — Shawn, 35, Ithaca, NY

Wrapping Up

Have you heard any weird first date stories that would rival these for entertainment value? What’s the worst, or the best, first date you’ve ever been on? Got any ideas for dates that are something a little different than the typical dinner-and-a-movie?

Let us know in the comment section below!

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