Dating can be a minefield of awkward moments, unexpected mishaps, and unforgettable blunders. But sometimes, the worst dates make for the best laughs!

We’ve all been there — navigating the tricky waters of romance, only to end up with a story that’s more “oops” than “aww.” From blind date mishaps to creative loyalty tests, dating disasters are universal. But why cry over spilled wine at dinner when you can laugh about it instead?

We’ve rounded up nine hilarious jokes inspired by dating misadventures. Whether you’re single, taken, or somewhere in between, these punchlines will make your heart skip a beat — this time, from laughter!

A laughing woman | Source: Pexels

The Sunday School Surprise
I was swiping through a dating app and matched with someone who didn’t have a profile picture. Desperate for a change, I decided to take a chance and meet her.

I wasn’t expecting much, maybe someone a little rough around the edges, but when I arrived, I was floored. She was stunning: 5’2″, baby blue eyes, strawberry blonde hair, and all the right curves.

A young blonde woman | Source: Pexels

Impressed, I asked what she did for a living. “I teach Sunday school,” she said.

I’d never dated a Christian girl before, but I was intrigued. On the drive to dinner, I lit a cigarette and asked if she cared for one.

“Oh, heavens no,” she replied, “What would I tell my Sunday school children?”

A couple in a cafe | Source: Pexels

Fair enough, I thought. Some people smoke, some don’t.

At the restaurant, I ordered steak, she got lobster, and I requested the second-most expensive bottle of wine on the menu. When the wine arrived, she declined a glass.

“You don’t drink?” I asked, surprised.

A couple drinking coffee | Source: Pexels

She shook her head. “Oh, heavens no, what would I tell my Sunday school children?”

The dinner and conversation were amazing, but I couldn’t quite figure her out. On the drive home, I passed a cheap motel and figured, why not take a chance?

“Want to get a room and fool around?” I asked nervously.

A motel sign | Source: Pexels

She winked and said, “I thought you’d never ask!”

Surprised, I laughed and teased, “Really? What are you going to tell your Sunday school children about this?”

She grinned mischievously and said, “The same thing I tell them every week: You don’t have to smoke or drink to have a good time!”