The ‘Worst Date EVER’ Competition


via Callee MacAulay

In honour of All Hallow’s Eve, it’s time to break out some horror stories. Honestly, there is NOTHING more frightening and horrifying than a bad date.

How does the competition work?

You tell us (in colourful detail) about the worst date you have ever been on. I mean come on, we’ve all been on at least one horrific date in our life. The kind of date that wants to make you permanently give up on the opposite sex and join a nunnery/monastery. 

What do you win?

A lot of sympathy from our dedicated readers (which, let’s face it, is a lot better than a real prize).

So get writing and post your tales of horror and woe in the comment box at the bottom!

 What traumatic tales do you have to share with us?!


  1. LOL!!!!!!!!! so did you ever make it to the beer?! or did you end the date after finding the license plate?! HILARIOUS! i don’t allow men to pick me up, either!!!

  2. Not sure if this counts, because it was with a serious boyfriend, buuuuut…

    My boyfriend at the time and I decided to do a little “getaway” of sorts. Basically we got a hotel room and were going to go out to dinner and pretend we were on a real vacation.

    Well, after drinking a little too much while watching My Cousin Vinny in our room (yeah, I don’t know why we spent money on something we could’ve done at his apartment instead), the darling decided to confide in me.

    He told me that sometimes he heard voices in his head. When I pressed him a bit to try and understand what he meant he said “Well like, right now. They’re telling me to kill you.”

    Ummmm. YEAH. Luckily I made it out of that relationship alive and with nothing more than a bit of emotional trauma!

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  4. Umm this story is a lot like the other commenters, but it was a first date. This girl, that in all fairness, I had been friends with for about a year, finally got up the nerve to ask me out. We went out for pizza and then back at my place she proceeded to tell me the most intimate, darkest secrets of her life. I just wanted to watch a movie and cuddle. #Awkward.

  5. Found your blog through From Sugar With Style. Love it! I’m inspired to write my worst date story, but it is really long. I’ll put it on my blog and then you can read it if you want to. Thanks for making me remember how lucky I am that that guy is not in-country anymore.

  6. This is not really a worst date, just one that was weird and a bit funny.

    On a second or third date a guy says he should tell me something. Here it comes, I thought. Didn’t expect this, but he tells me he doesn’t have balls! An accident saw to that apparently.

    At first I thought he was joking so I laughed. When I realized he wasn’t, I felt terrible. Anyway, I liked him and didn’t let his admission change anything – to be quite honest I was a bit intrigued.

    Things progressed and I found out that there were no problems in the bedroom department, but I was glad he “had the balls” to tell me beforehand – it would have been a bit freaky discovering the empty sack without warning.

    Up until that point I didn’t didn’t even know guys whose testicles had been cut off could even have sex! But apparently they can, quite well in fact.

  7. I went to one of those dating events with crazy games and fell for a guy in a puffy shirt. He had long hair. I agreed to meet him an hour and a half train ride from my house, even though he had a car. I got in the car and he told me he had just got back from a polyamoury party. I was not sure what that was but I had a feeling it was not something I was interested in. I decided at that point I was being rejected but I wanted to eat. When we got to the restaurant he took off his coat and he had a tee shirt on with a giant hallucinogenic mushroom on it. I noticed a medical bracelet he was wearing as I had nothing especially positive to say about the mushroom, I asked about the bracelet. He told me that the bracelet served to indicate that his head was to be harvested and frozen after he died. He had paid several hundred thousand dollars for this, not being able to afford the whole body deal. We went to see Galaxy Quest afterwards. I had already seen it 4 times but this seemed to be a fitting ending to an out of this world date. I learned some lessons that evening. I seem to have a thing for narcissists who aren’t that into anyone but themselves and I can enjoy myself no matter what.

  8. Had gone on a couple of dates with a lovely guy who I thought was as into me as I was into him. Ummmm…not quite. Went out on a date – took me out to a fabulous African restaurant. I was laughing at all his (not so funny) jokes, on my best behaviour, wearing my best outfit and convinced he just adored me. Not only that, he was taking me to the movies – to see Titanic. I took that to be a sign that he was keen. Like Leonardo was keen on Kate. Not quite. We bought our popcorn, I was on cloud 9 thinking it was all so romantic. Sat down, lights went off and then he says “I think you are nice but I don’t like you like that. We should keep it as just friends”. And then the music started. I was shattered. Needless to say, it was the longest film in history as far as I was concerned. I decided I needed a breather in the middle of it so I went outside and had a mini sob and then realised all the doors were locked to get back in (the late, late session). I ended up sitting in the gutter, waiting for the film to end so I could get a lift home. My date had barely noticed I was gone. “Wasn’t that the most beautifully romantic film you’ve ever seen, Sonia?” Umm…no.

  9. My “worst” date isn’t so much a worst as a funny. I went on a one-time date with a friend of mine, he was so nervous he downed the entire pack of twizzlers he’d bought in less than a minute and at intermission (it was a long movie) he complimented me on how my hand was the perfect size to hold–not too big, not too small. We kissed in the theatre and heard an audible groan from the couple a few rows behind us. At the end, we tried to walk home but being that it was winter and the temp had dropped below zero while we were in the movie, we ended up stopping in a coffee shop for something hot and I called my Mom to give us a ride (late high school years)–so no romantic ending there! We did have fun though and remained friends though we never dated :)

  10. Hi there! Thanks for visiting my blog “Eyes to Heart” and liking my post “Seascape …” … Your blog looks like a lot of fun. Too bad it wasn’t around when I was on the dating scene ;-) … I look forward to checking it out more soon. Thanks again … Be well … Dorothy :-)

  11. Thank you for liking one of my posts! Your blog is awesome – I love how realistically relationships are portrayed, for better or worse ;)

    My horror story – The guy I was dating was a secret alcoholic. We had been friends for several years, and no one really knew the extent of his problem. On this particular night, right after we decided to try and become an “item”, he had decided to drink a bottle of whiskey to pre-game, and then to follow all of this whiskey with some sleep-aid, because “when you fight the sleep, you get REALLY messed up”. So, of course, I decided to have sex with him anyway, because that was the obviously logical choice, and plus, he would recite Hemingway poems to me. Anyway, during the act, he went into some kind of black-out, neurotic rager; he bit my face (right above my eye – bruised it, with teeth marks and everything… try explaining THAT one to your boss)and then spit on me and yelled “you like that, bitch?!”. He then passed out cold, and peed my bed.

    True story lol

  12. Fortunately I have managed to block most of the evening from memory. It was a blind date that didn’t get off to a great start and got progressively worse. I think it was the point that the guy took his teeth out to slurp his noodles in Wagamama’s that tipped me beyond the point of wanting to live!

  13. Odd that one of my worst dating experiences happened on Halloween when the man I was supposed to be seeing exclusively was surprised because my children were done with trick or treating earlier than expected and he was with someone else when I stopped by.

  14. One must practice the comic scripts beforehand at home.
    If I knew how to bake cookies, I would do that and send over a
    care package but Im much better at telling jokes so
    I go there and entertain, shake hands and thank the men and women who serve our country.
    Wouldn’t it be nice if we could take a magic pill and have a perfect relationship.

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