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Our Team Reveals Funny Dating Stories to Our Daters: Live!

Couple sharing an intimate moment on a beach at sunset with a ferris wheel in the background.

On Valentine’s Day you mostly only hear about the romantic moments, the successes and the couples that are just made for each other. But what about if your Valentine’s Day didn’t look like this this year? Well, we decided to throw out tradition and instead laugh together on a very special #Dating live stream all about funny dating stories!

Our team at #Dating is full of dating experts, but that doesn’t mean we haven’t had our fair share of bad dating stories over the years. We decided to use our brand-new live stream option on #Dating, where we gathered up some of the best stories to present to you: our amazing dating community! What a way to celebrate this fresh feature! But fear not if you missed our live stream on the #Dating app where we revealed all, we’ve got a roundup of some of the best stories below.

Group of friends enjoying drinks at a bar.

An Overcrowded First Date

To kick off, let’s hear a story about a team member’s now-husband! So it can’t have put them off that much, right? Although, this was a pretty awkward first date:

“My funny dating story is with my now-husband. We were first colleagues and he invited me for a beer. In his mind, this was a date invitation, in my mind this was a “let’s hang out after work” invitation, so naturally, I invited like 20 other colleagues. You can imagine his face when he entered the bar and found not only me, but 20 other people sitting at the booth, laughing and having fun… we are married now and our ‘first date’ is a funny party story 🙂

That must’ve been a very confusing moment! We’re pleased it worked out and their natural chemistry and magnetic attraction shined through, even in the accidental ‘group date’. Going from friends to dating is no easy task, but some tips can make it a lot easier and maybe you’ll be end game too!

An adventurous couple sliding down a water slide together at an amusement park.

Ready To Get Naked…Or Not?

Our next story is about a trip to a waterpark that turned into a very weird date! How would you react to this?!:

“Went on a date to a waterpark that also had a spa area. Since we didn’t plan on going to the spa area I was not worried about having to be fully naked, as this is quite normal in spas in Germany where the date took place. However, when we got to the waterpark we discovered that past a certain time, the ENTIRE water park requires EVERYONE to be nude! Since we were not at that level yet…we went to a restaurant instead 😁.

It would feel pretty embarrassing to turn up at your date location and find out you actually need to take off all your clothes! You can’t help but feel for these two, but we’re glad they managed to communicate effectively and end up somewhere else where they would feel more comfortable. So many countries have different traditions and there may be some hidden surprises when dating in another country or even someone from another country. Communication and clarity is key when you come across cultural differences.

A couple engrossed in a movie at the cinema, captivated by the screen, surrounded by dimmed lights and other moviegoers.

First Date Sleepies

We had some even more amusing first date stories come through from our team. How embarrassed would you be if this happened to you on your very first date?:

One of the first dates I had with a guy was a trip to the cinema. I’d booked us tickets to see an indie film (you know, to show him that I’m “cultured”). However, within the first 30 minutes I fell asleep, and woke up a little while later dribbling on his shoulder.
Now, personally, I like to think it’s because I just felt so comfortable around him from the get go – but he definitely was not impressed… Anyway, 8 years later and we’re still together – so apparently it didn’t put him off too much haha 😏”

This is not the perfect fairytale of a first date – but we’re pleased it had a happy ending! Even though we all love funny first date stories, this one certainly has its own charm to it. Have you ever felt comfortable enough to chill out and relax like this on a first date?! That’s when you know there is a special bond! But if you’re feeling nervous rather than relaxed, we have so many first date tips and advice for you, if you don’t want to end up dribbling all over your crush!

A man on one knee, holding a ring, proposing to his girlfriend on a beautiful sandy beach with waves crashing in the background.

The Worst Proposal Soundtrack

Plus all of the crazy dating stories, we even took it to the next level and shared a very funny proposal story:

When I proposed to my wife: after a long and exhausting hike around a mountain area we reached a cute area with a river side and some buildings, I decided it was the right time. In the middle of the whole process, a big and sweaty man comes out of one of the buildings smoking a cigarette and lets out a grade-10 fart that was heard in half of the park and probably from space as well! I wanted to invite the guy to the wedding, but my bride-to-be said no.

Maybe when you’re being proposed to, you picture violins playing in the background, maybe even a soothing piano for a moment in your life you’d want to remember forever… not those types of trumpets! This just shows that sometimes, you can plan all you like, but on dates and even your engagement, you just have to expect the unexpected and take the rough with the smooth. Embrace uncertainty! If you and your partner can have a laugh about it, it’s certainly a good sign for a healthy, long happy relationship and maybe even marriage.

A couple sightseeing having their photo taken by a passerby

A Real Life Angel

The final story we want to share ends happily ever after – but still has some very awkward moments!:

Back when I was on a kind of “first date” with my now wife, we were in that phase where we weren’t sure how to label our relationship. We were walking around Frankfurt in Germany and a tourist couple asked us if we could take a picture of them. Afterwards, they offered to take a picture for us, so we started posing but with the awkwardness of not knowing how to. The guy started telling us to get closer and hug each other. After that encounter, we went for a coffee and a much-needed talk. After 15 years of marriage, I often think of that tourist as the best accidental wingman ever.

This matchmaker is actually cupid – and they don’t even know it! If there is one thing this story teaches us, it’s that it’s okay to take the plunge and tell your date how you feel. Don’t ignore the signs, even if they come from strangers – just go for it!

The laughs were infectious as we shared with you some of the dating stories from the team. Hopping onto a live stream was so much fun and hopefully we’ll see you again on another one soon. Remember to check out the Live tab on the #Dating app to find out who’s currently live and maybe even start your own stream and who knows, maybe your Valentine’s Day could look a little brighter next year! We hope you enjoyed reading them back and hopefully, you now know that you’re not alone if you’ve ever had a date that didn’t go as planned, even the experts can get it wrong!


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