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This is a question Asking people out

Tell us your biggest successes and most embarrassing failures. Not that we're after new chat-up lines, or anything.

(, Thu 10 Dec 2009, 11:36)
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I'm not the suavest cat in town when it comes to the ladies,
but add my mates into the mix, and my chances go from small to none. One seems to constantly try to convince me no-one's interested, another seems to have an urgent compunction to attempt to knob any female in range, a craving which is magnified by about a million if I show the slightest interest in the lady in question. I love them dearly, but they can be unbearable shits at times. Not so my best mate, however. He has, for as long as I've been single, made a genuine effort to help me with the ladies.... in fact, for a good while, he was more interested in getting me a woman than I was. There are only two problems with this, however....... one, while we all need a wingman occasionally, you have to fly your own plane, and two, he's about as subtle as a pit bull after some sausages. This is seemingly a trait shared by his mum an dad too, unfortunately. If he is my wingman, he flies a lancaster bomber.

When his mum said she knew someone perfect for me, I immediately dug my heels in. They somehow managed to arrange a meeting though and I was pleasantly surprised! Not only was she very pretty, she also seemed nice. A shame, then, that any chance of me actually having a conversation with her was overshadowed by them sitting staring at us, and occasionally (and hilariously, I might add) pointing out the obvious awkwardness of the situation. I basically got backed into a corner and made to feel a proper tit, as I'm pretty sure she did too. They were only trying to help, mind, but it....... well, it didn't.

She came to my mate's party about a month later, and I thought maybe this would be a chance to get to know her better and perhaps let her see I wasn't the arse I'd been made out to be. After a while (and a few courage potions) I went over and said hello. We had a bit of a chat and things were going OK...... until in steams my mate to "help". What followed was about 30 minutes of him bluntly asking her what she thought of me with me sitting right there and her looking twice as embarrassed as before. He eventually turned to me and said "Tell me you wouldn't like to wake up next to that in the morning!" Every time I tried speaking to her after that he or someone else was there murmuring "get in there" and giggling like an idiot, completely missing the fact they were embarrassing the hell out of the poor girl, and me too, for that matter. I eventually felt such a twat that I wandered off, but my tacketty booted mate kept on at her in my absence until my other mate arrived and started trying to 'get in about her' himself. At least he failed. That's one thing.

She sent me a text a few days later to let me know her number, but I suspect my pal, or his mum, had "persuaded" her to, as she had that kind of "Everything is fine there is no-one behind the door with a gun making me say this" kind of air about her.

This was all years ago, though, back when I pretty much wanted to stay as far from the "fairer" *pfffft* sex as possible. I think he thought he was being cruel to be kind. He's much better these days though, and I think he's worked out that trying his hardest to make me look as much of a twat as possible probably doesn't help, in the long run.... not since primary school, at least.
(, Wed 16 Dec 2009, 3:09, Reply)

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