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Fancy A Giggle? 15 Glossies Share Their Real-Life Dating Disasters!

Fancy A Giggle? 15 Glossies Share Their Real-Life Dating Disasters!
Emily Cotton
Beauty Editor3 years ago
View Emily Cotton's profile

Maybe you’ve been there. Maybe you’ve found yourself on a date, that you’re not even slightly interested in and things just keep going from bad to worse. Do you sit through it, hoping things will miraculously improve, or do you cut your losses, run and use the experience as a funny story to share with friends 

If you’ve not had your own dating disaster – and the closest you’ve ever got is hearing stories from your girl pals – then think yourself lucky! But these girls have... 


Cringe-Worthy Dating Disasters!

We’ve collated the cringiest, funniest, most laugh out loud worthy dating disasters from Glossies that are guaranteed to give you a giggle!

WAY Over Prepared!

He turned up to a first date with an overnight bag...!

Drunk And Disorderly

I once went on a date and got so drunk beforehand that I left my bag in the taxi on the way to his. I then closed myself in his bathroom with the light off somehow and thought I was trapped somewhere. I started shouting for help and banging on the wall... He found me naked on the floor under a towel. The next day I had to call in sick to work, get an Uber to the estate agents to pick up spare house keys, and also track my bag downSomehow, he still asked me on a second date... Sophie, 29

Bon Appetit!

Went on a dinner date and he decided to show me an extremely long nipple hair through his shirt...

Looking For More Fish In The Sea

First date; he spent the whole date on Tinder. I could see as there was a mirror right behind him!

Best Friends, One Boy

He messaged my flat mate in front of me... He clearly didn't know I lived with the other girl he was messaging!

A Change Of Plans

I went on a date with Spanish guy I met on tinder. We were having a nice time, good chat, few drinks - though I was driving so no alcohol for me. Suddenly, after about an hour and a half, he says: ‘so what are you doing tonight?’. I was like what?’. In my head I'm thinking, ‘I was under the impression I was on a date with you... He follows up with ‘I'm going for a late dinner with the lads. Spanish people eat late’. I just replied with oh right, okay’I never saw him again... Thank god I drove myself! Emma, 34

Yes Sir!

I once dated a teacher who repeatedly corrected my grammar. It didn't last long.


We went for a second date and he had one of my Facebook pictures as the background on his phone...

Mother's Approval

His mum turned up and asked why I didn't kiss her son!

Welcome To The Gang

I met with a guy I met from tinder and he took me to an expensive Mezze restaurant in Maide Vale. He then conveniently forgot his credit card... I think he felt bad, so to make it up to me, he took me to his mate’s apartment to introduce five of his friends, all at once...” - Charlotte, 26

Perfect Etiquette

He took food off my plate without asking, didn't like it, so spat it out on the table!

A Scarily Good Day Out

An ex-boyfriend told me we were going to the park, and then took me to a cemetery instead.

An Artist In The Making

A guy I met at the pub wanted to show me his paintings... that he'd done with his own blood!

A Little Too Full On...

I once went on a (sober) date with a guy who: 

  • Spent half the date telling me about his ex who cheated on him 
  • Kept talking about how he likes to look after his girlfriends 
  • Wouldn’t stop putting his arms around me 
  • Called me the perfect woman less than an hour in 
  • Invited me to go on holiday with him  
  • Invited me to an ESheeran concert that he 'just happened to have front row tickets to' after I said I didn't like Ed Sheeran that much 
  • Then bombarded me with texts on the way home” - Fiona, 25

Petty Cash Bandit

When the bill came, I paid. But when the waitress brought over my change, he took it!

How To Deal With Bad Date Situations

Obviously, there are bad dates, and there are bad dates,” says Alexander Patall, resident dating expert at Datingroo. “If you find yourself getting the ‘ick’ early on, sometimes being cruel is kind. If you do decide to cut your date short, being upfront that you have to leave will always be a better option than making a backdoor exit. 

Honesty is also the best policy if your lack of interest on a date is down to our own feelings. If you’re on a date with somebody that is making an effort, but you’re just not interested - try and let them down gently,” adds Alexander. “Be honest that it’s your feelings and not anything they may have done. ‘It’s not you, it’s me’ is a well-known cliché - but it prevents the other party wondering what they did wrong. 

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Emily Cotton
Beauty Editor
View Emily Cotton's profile
I'm someone who loves getting glammed up, but I feel like I never have enough time. Frequently running between work, the gym and seeing friends means my makeup routine is quick and often touched up on the go. Therefore, beauty products that serve as multi-purpose are perfect for me - a blush that works for cheeks and lips is a must in my makeup bag!