5 Bizarre First Date Horror Stories That Will Make You LOL!

Did you know that almost half of the U.S. population — a whopping 45.2% — isn’t married? 110.6 million people over the age of 18 are living the single life!

This is a far cry from our mom and dad’s upbringing. In 1960, 72% of adults in the U.S. were married.

It’s safe to say that times have changed. It’s not our momma’s dating scene. Americans are staying single longer, looking for that perfect fit, not settling.

This opens singles up for a lot of awesome opportunities. But it also leaves them with a slew of first date horror stories.

Luckily for us, some of these stories have gotten recorded. So take a moment to stop perusing OkCupid and get ready to cringe — or laugh out loud.

1. That Time Amy Schumer Got Schooled 

By someone who had no idea what he was talking about.

Amy Schumer once relayed a hilarious tale to Live with Kelly and Michael. She told a story about a date that was horrible in more ways than one.

First, he came prepared with dating questions. You know, those cheesy, get-to-know-you prompts like, “What are your parents like?” and “Tell me your favorite pastime.”

His conversation starter of choice was, “If you could have lunch with anyone, living or dead, who would it be?” Schumer responded with the writer Mark Twain. To which her date replied, “No — it has to be somebody real.”

That’s five stars on the cringe scale from us!

2. That Time Someone Got Caught Reusing Pick-Up Lines

Online dating can get awkward. Services like this dating site have produced their fair share of hilarious tales. 

22-year-old Veronica didn’t have time to craft a new pick-up line for each prospect. On Tinder, she stuck with her go-to: “You can only listen to one song for the rest of your life. Which one?”

(There are those cheesy dating questions again!)

Turns out she was messaging 2 people at the same time. .  . using the same line. . . and those 2 people were in the same room! They ended up revealing that fact, but not before a little teasing.

That’s what the block button is for!

3. Perhaps the Most Dangerous of Our First Date Horror Stories. . .

Is the story of the guy who didn’t leave his date unscathed.

Then 14-year-old Ned took his date on a fishing trip. It was the gal’s first time fishing. At first, all was fine — she even baited her own hook!

But as she went to cast, she flung her rod backward — where it made contact with Ned’s cheek! He got rushed to the ER by his parents. To this day, he stills sports a scar.

4. That Time Someone Dissed Tina Fey

Speaking of awkward — college dating is a trip!

Tina Fey once went on a date in college with a jerk. And although he must’ve liked her enough to go out, he didn’t like everything about her.

He proceeded to say, “You’d be really pretty if you lost some weight!”

Ahem — excuse us? Waiter, check, please! But first, bring a dessert I can shove in my face in front of this guy!

5. That Time Kelly Osbourne Broke Her Wrist

We lied — we’ve got one more dangerous first date disaster for you.

Kelly Osbourne’s first date left her broken — not broken-hearted.

Her date wanted to give her a little smooch, but Kelly didn’t want a kiss. She leaned back, not knowing that a set of stairs awaited her. Three stairs and one broken bone later, Kelly ran off down the street.

We would’ve done the same thing!

It Takes All Kinds

Before you land your Prince (or Princess) Charming, you’ve gotta go on a few bad dates. You’ve gotta build up your inventory of first date horror stories. You’ve gotta kiss a couple of toads.

But it all might bring you to the one! And when it does, it’ll all be worth it. (We hope.)

Here are 10 weird, adventurous ideas for your next date! Good luck!

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