The Worst (and Funniest) First Date Story I’ve Ever Heard


When you tell people you write a dating blog, one of the first things they will do is tell you dating stories.  Romantic dating stories.  Funny dating stories.  Awful dating stories.

Like most people, it’s the bad dates which I tend to find most interesting.  Mainly because I very rarely have bad dates.  Over the two years I’ve been single, I’ve worked out ways to ensure I always have fun on a date … but not everyone is so lucky.

This week I heard probably the funniest first date story I’ve ever heard.

A friend of a colleague was online dating.  She’d had the usual issues – turning up to dates to discover men looked nothing like their profile pictures, and fending off a stream of creepy messages.  So when she started chatting to a particularly attractive guy, she began to get nervous.  He just seemed too good to be true.  The more she checked him out, the more nervous she got.  He was model-gorgeous, and a wealthy high-flier, and every online search simply revealed more and more good stuff.  Where was the catch?

By the time she went on the date, she’d worked herself into a complete state.  To calm herself down, she went for a pre-drink with a friend.  Dutch courage.  Except she ended up drinking an entire bottle of red wine.  As predicted, when she finally met the guy, he was everything he had promised to be, and more.  Gorgeous, successful, intelligent.  Nerves got the better of her, and she reached for the red wine again.


At the end of the date, 2 bottles of red wine down and feeling rather worse for wear, she didn’t say no when he invited her back to his flat.  His luxury, pristine flat.  A flat where everything was white, including a beautiful white suede sofa.  (Yes, this is going where you think it’s going.)

Things got a bit steamy on the sofa, and the rather drunk girl went to give her date a blow job.

She placed her lips around his cock, her gag reflex kicked in, and she projectile vomited all over her date, and his immaculate sofa.  Jumping up in surprise, she only ended up spraying her red wine vomit more broadly across the sofa and the pristine flat.  Like a scene from a horror film.

At which point she got up, leaving her naked date on the sofa, his crotch filled with a pool of bright red sick, staring up at her in disbelief.  And she walked out of his flat without a word.

The morals of the story?

1) No matter how bad your date goes … remember there’s always someone out there with a worse story! 

2) There are some good ones out there … not everyone exaggerates or lies on their profile!

3) Getting a bit drunk on a first date? Reach for a Coke, not a cock! 😉 


Miss Twenty-Nine xxx



1 Comment on The Worst (and Funniest) First Date Story I’ve Ever Heard

  1. Oh my gosh that’s disgusting! I wonder if the guy thought he had anything on his penis which caused her to up chuck?

    Anyway, here’s a funny (but not as funny) and more horrific story. I feel for the dude in this one:

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