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15 of the funniest dating fails

February 11th 2015 / Katie Robertson Google+ 15 of the funniest dating fails


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In the spirit of Valentines day, we've been rounding up our worst dating disaster stories - a gentle reminder of why a night out with the girls might not be so bad after all...

Dating can be an all round nervewracking process - awkward silences, dinner choice dilemmas and the eternally difficult task of trying to find an outfit that’s both classy and sexy (if you figure this out please let us know).

While most dates pass by as either dissapointingly uneventful or with hope for the future, there are those few golden experiences that are so painfully cringe-worthy, you couldn’t make it up if you tried. Mortifying and haunting at the time, we’ve come to the conclusion that nothing quite builds strength and character than re-living these terrible dating experiences - or at least that’s what we keep telling ourselves...

So, rather than lamenting over our love lives we’ve been digging around in the dark depths of our past dates to bring you 15 of the best - or in some ways the worst - ultimate dating fails from within the very own Glossy Posse team.

"A guy once decided to fill an awkward silence with 'hey, so I always wondered - what's it like to be on your period…?'"

"I once had a date where the guy made everything in a cup in the microwave. The main was 'egg in a cup' and the dessert was 'chocolate pudding in a mug' and we drank wine out of cups. Never explained and just so, so bad."

"Once when me and my date were sat quietly in the cinema waiting for the film to start - my date was chomping his way through his pick 'n' mix and trumped very loudly!"

"(When I say I love Bourne films.)

*flirty face* “Funny you should say that, as people say I look just like Matt Damon.”

(Doesn’t look like Matt Damon.)"

"I was out to dinner with a guy and my contact lense started rubbing and stinging really badly. I didn’t want to cause a fuss or let him know but tears began to stream down my face. As he looked at me in complete shock and concern I panicked and for some reason said that Chinese food made me really emotional. I didn’t get a second date."

"One guy spent the first half hour of our first date telling me in gruesome detail about the root canal he had had that week. I could barely keep my drink down."

"On a first date, a guy once asked me 'so have you ever wondered where you might like to go on your hen do?’, as well as, ‘do you have any pictures of you as a baby?'..."

"I once had a date at this guys house and he'd pulled out a version of 'Truth or Dare Jenga' for for us to play that involves people writing dares on some of the blank bricks. After playing for about five minutes it became pretty obvious that he'd labelled every single bare brick with 'kiss the other person in the room' - we were very sober and I'd only met him once before. It was horrendously awkward to say the least."

"When a guy came to pick me up from my house once my dad came outside and said ‘Oh so you’re Henry right? I’ve heard a lot of good things about you.’ My date replied with a stoney face ‘no actually, I’m George.’"

"After going on a couple of dates with this seemingly ‘normal’ guy, on the third or fourth date he started asking me how much I liked him on a scale from ‘one to penguin’. I answered thinking he was just being a bit kooky. He then went on to ask the same question using at least 15 other animals and wouldn’t give up until I answered. I now forever regret giving him full penguin points..."

"When having drinks with a nice, good-looking guy we got talking about our biggest character weak points. I think I said something along the lines of 'I can be a bit of a clean freak a times.' He responded, while chuckling, 'I have this problem where I totally loose interest in girls after I sleep with them.' Safe to say, I never let it get that far…"

"I went on a date with a guy once and thought it was going really well until he got drunk and announced how he had £10,000 of credit card debt and how his main ambition in life was to marry a stripper in Las Vegas one day."

"I decided to chat up a table of men once. Feeling smug when they were impressed that I had the guts to talk to them, I was just choosing which lucky guy would be the object of my affection when I asked them the question 'How do you all know each other?' I did not expect the answer I got - 'Antenatal class!' I slipped away quietly, but not before they showed me pictures of their babies."

"I had a date with a guy I really liked and he was planning on taking me to the comedy store. But when I looked up who was playing that night I realised a guy I had been on a really bad date with was headlining. I knew I had to tell my date in case he dragged me to the front and the comedian spent the whole night talking about his bad dates and directing them towards me. My date laughed it off as 'one of those things that happen' but he didn't take it quite so well when my ex date appeared on stage - 'God how short is he?' and 'not the best looking guy you've dated is he?' It would have been fine if my ex date hadn't been funny - but he really was, so as everyone ripped into laughter around us I had to contain my big belly laughs, while my now date sat there with a face like thunder!"

"Once this guy invited me round his house for our first date and when we got into his bedroom there were lots of perculiar rectangular patches over the wall. I asked him what it was about and he waved it off as old photos he didn't want up there anymore. When he went to the bathroom I came across a pile of pictures of him and his ex-girlfriend - I later found out he'd only broken up with her the day before..!"

Follow us @getthegloss and Katie @KatieRob20


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