Funny dating stories including one of my own

It’s Wacky Wednesday, and today is all about funny relationship and dating stories. If you have any, please send them through! I’d love to hear them and share them on your behalf. Names and situations can be changed to protect the innocent (or the guilty!).

To kick off my very first Wacky Wednesday episode, I’ll share an interesting date I went on once.

My Own Funny Date Story

I was working in Brisbane City at the time, and I met a guy—I can’t remember how I met him, but anyway, he organized for us to meet at the Bavarian Beer Cafe on the river in Brisbane, not far from where I used to work.

When I met him, he seemed okay. Not a stunner, but not gross either. We had a good conversation for about an hour or two. He said he was getting hungry and invited me to a nearby Japanese restaurant. I agreed, and we had dinner there. He paid for everything, which was lovely. At the end of the night, we hugged, and I kissed him on the cheek since I had to get home.

For safety reasons, I always made sure to get myself to and from a first date. So, I was on the CityCat (a catamaran that runs down the river) heading home when he sent me a text thanking me for the date. I responded, thanking him for dinner and drinks, saying it was great to meet him. Then things got weird.

He texted, “By the way, I like to be dominated.” What?! He elaborated further, and then sent a photo of his… let’s call it a small surprise. I was on the boat, cracking up laughing, trying to keep it quiet because other people were around. Needless to say, there was no second date.

More Funny Date Stories

Here are five more hilarious date stories from others that are sure to give you a laugh:

1. Mom’s Date Too “A guy I met on OKCupid brought his mum to the date. She spent the entire time talking about her work and showing old basketball photos. He and his mother sat really close, giggling and kissing each other’s cheeks.” Awkward!
2. Joke Critic “In a fairly empty lounge with a TV showing a monologue from Jay Leno or Conan O’Brien, my date dissected each joke, explaining why they weren’t funny. He proudly mentioned he does this at parties and comedy shows too. What a riot.”
3. Wedding Crasher “He took me to a wedding reception of someone neither of us knew for free food.” Nothing like a free meal, right?
4. Funeral First Date “Instead of rescheduling, one guy took me to a funeral on our first date. Afterwards, during dinner, the conversation was so awkward due to having nothing in common that I couldn’t even look him in the eye.”
5. Acro Cats Adventure “On one of our first dates, my boyfriend (who she obviously stuck with after this) took us to an event called Acro Cats. It’s a travelling circus for house cats. The cats were pretty well-trained but made it clear that cats will be cats and do whatever they want. It was pure chaos with several cats wandering around the audience. Funny, awful, and amazing all at once.”

I hope you enjoyed these stories. Remember, dating is a journey, and sometimes the detours make the best tales. Have a great Wacky Wednesday, and I look forward to talking to you again tomorrow!