WH Logo

Sign up and stay up-to-date with us!

    Your Worst Dates. Ever.

    Your Worst Dates. Ever.

    Dating is hard. Whether we meet someone online, in person, or through a friend, there is always a chance for a first date to go horribly, horribly wrong. Of course not every guy or girl is going to be a total winner (as we learnt over on An Education in Dating) and it may take a while to find a person who we click with, but sometimes the things that women endure during a first meet are so outrageous that they are actually comical – maybe not in the moment, but definitely afterwards. Last week on social media I pleaded with you all to share you best First-Date-Gone-Wrong stories.

    The results are in, ladies. 

    When they’re not actually Single

    Got punched in the face by his girlfriend on a date …. He said he was single, she disagreed! Mortified! 

    Retro Chic

    First date with my now husband – we were in a bar and I went to pull my phone out of my bag and pulled out my gigantic 90’s style remote control. I’d chucked it in my bag for some odd reason before I left, probably thinking it was my phone. He thought it was hilarious and said it’s the moment he knew he liked me. 

    Getting Lippy 

    There was the time I pulled my lip balm out of my bag, only realising too late that I was actually rubbing a tampon on my lips.

    Sweaty Betty

    After talking online for a while, we decided on a halfway picturesque village.  It turns out he had fed me a load of lies about his height (I am 5ft 10). He was also strangely dressed. It was a very hot day and he had on an old crumpled jumper over an even more crumpled shirt. I wanted to run but thought it wouldn’t hurt to spend a couple of hours after the long drive as I’d already paid for parking.  Anyway he was as boring as hell and sweated profusely in his jumper and no amount of persuading was going to get him to take it off. The sweat was literally rolling down him like a river. 

    Cat Fished

    Met up with a guy after speaking online and phone for a few weeks…he turned up….lovely chap…..no teeth tho! My mind was blown!

    Love at First Sight

    I was set up with this really “nice guy”. First date he took me to his sister’s wedding. It was a bit awkward meeting ALL of his family, but meh, he seemed nice enough. Second date however,  he scattered rose petals through his house and up to his bedroom and then told me he loved me. I. Ran. A. Mile.

    So bloody awkward.

    Seen but not Heard

    The date was actually going well until I had a different opinion to him about something trivial, can’t even remember what. He looked at me disgustedly and told me it wasn’t very attractive to not agree with him and that his sister would never disagree with him. I told him we probably weren’t suited and maybe he should go sleep with his sister instead.

    Train Reaction

    I met someone on Tumblr, which is an image sharing sight after I got out of a 6 year engagement. He was from Poole and I was living in Falkirk, Scotland at the time. So we FaceTimed a few times and really hit it off and the next time I was heading home for a visit I said we could meet up! I was really excited, right up until I saw him from my train window as we pulled into Kings Cross.

    Now, I’m not being mean but I’m 5”2 and rarely think anyone would be shorter than me, well when I departed the train I noticed I stood a good 3/4 inches taller than him. I decided to not be so shallow and get over it, because what’s height anyway? We went to the pub inside Kings Cross station, the chat was flowing and I started to feel more comfortable. As we were heading up the escalator he attempted to pick up my very heavy and large suitcase for me and fell backwards down the escalator into a lot of commuters, who completely  ignored him!! I dived for him to try and help and ended up on top of him as my suitcase and all of its contents start tumbling down by peoples ankles. Most notably my ‘saucy’ underwear I’d brought down incase the date went well! 

    We compose ourselves and head into the pub (after A LOT of awkward fumbling and grabbing). So we find somewhere to sit and I decide to buy us some drinks! I try to stumble through the next half an hour, but alas, the conversation had dried up. As I’m making my excuses to leave, I notice said ‘saucy’ underwear from the escalator poking out of the top of his jean pocket.

    Safe to say we never spoke again and I was left with a horror story for anyone meeting people they meet online.

    Mama’s Boy

    “Do you what I like about you Helen, you have the same name as my mum!”

    He genuinely seemed turned on by it! 

    There we have it. Well done Winchester, we’ve nailed it!