Home > Adventures in Dating > My top 3 most awkward moments in dating

My top 3 most awkward moments in dating


After quite a lot of waffle about woe. I thought I’d lighten the mood a bit with three of my most cringe-worthy dating moments. These might be in order of badness, I haven’t decided yet.

A Holiday camp in France, sometime in the 90s

My first holiday with friends. I was about 13, I went with two friends and their parents. It was really exciting.

We stayed in huge tents and spent all day swimming, buying bangers or pumping coins in to dated arcade machines. It was the first time I’d ever heard Stairway to Heaven. It blew my mind.

My two friends quickly got rather pretty ‘holiday girlfriends’ and spent a lot of time snogging them in the café.

I did not. So to cure this they took me on a tour of the holiday camp, presenting me like a socially awkward horse to all the ladies in vaguely the right age-range to see if any of them would go out with me.

They didn’t. I spent a whole afternoon being peered at from caravans followed by a slow shaking of heads. Just thinking about it still makes me shiver.

Secondary school, first week

We had a sort of trial week where we went to the big school. It was very exciting because it was a BIG SCHOOL with thousands of pupils. I was 11. My previous school had 4 people in my year.

It was a culture shock. I spent the entire time worried that someone would trick me into taking LSD and/or flush my head down the loo.

There was a girl there, she wasn’t actually going to the school but had gone along for a week to be with her friends. I fancied her and wrote her name all over my pencil case.

I wrote her a letter too, after the week. The letter was quite cool but for reasons I don’t quite understand still. I used a stamp on the envelope to make it look like it had lip marks all over it. Huge red lip marks.

This turned it from a private message of affection into something her HUGE brothers found. There was quite a lot of mocking. I was at the same sailing club as her brothers, they were instructors. I got wet.

House party somewhere remote, after being at an awful club

I went to a terrible club near where I grew up. It was the only club in a small town. They showed RUDE VIDEOS in the bar. My DJ partner and I arrived late and sober because we’d been at a gig. This sounds cooler than it is, as far as I remember we’d been DJing in the function room at a golf club.

Some friends of my DJ chum were there, which is why we’d gone to this dive. We chatted for a bit and had a couple of drinks. There was a girl there.

She took a shine to me, I knew this because when we were stuffed into a tiny car going back to her place she kept licking my ear and biting my leather jacket (vintage 70s obviously).

Back at the house she invited me to stay in her bed. I did. Then my DJ chum appeared and jumped in too. Things got awkward, because she didn’t seem to want him to go.

I’ll never know if she was trying to arrange a threesome or not because I spent the rest of the evening and most of the morning shivering in in the kitchen in just my underpants (I’d left my clothes in the room when I stormed off) until her parents reappeared…

  1. January 23, 2012 at 6:07 pm

    Oh dear. I feel like I shouldn’t be laughing, but I am…

  2. Ed
    February 12, 2012 at 7:27 pm

    Ouch! I went to holiday camp in france with my life-long, so-called best friend when I was 14. On the first day I got super high on all the excitement and allowed myself to be egged on to shave my eyebrow off, which made me look pretty darn freaky (in hindsight, I should have shaved the other one off too). My friend, seeing the ridicule poured onto me, pretended that we’d met on the bus there and joined in with the jeerers without hesitation.

    Things got worse a few days later when I stole some porn mags from a shop and they were found in my tent (there was tonnes of porn going round, I was just the fool that got caught). The cool, sexy female camp leader adult, who all the girls idolised, gave me a humiliation session in front of the whole group, calling me a “little pervert” and a “sad-case”. I just about refrained from crying. After that the few girls that had at least shown me pity avoided me like an ebola victim.

    During those two weeks, pretty much everyone else (yes, even the chubby, freckly, sheltered ginger kid with glasses who missed his mum) lost their virginity or snogged, fingered, groped and petted their way into serious teen-on-teen action. The gruelling torment of this experience scarred me deeply (awwww) and it would be another 3 years before I went anywhere near a girl.

    P.S. I’m fine now.

    • February 13, 2012 at 3:45 pm

      Ed, that is epic.

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