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This is a question Flirting

Do you flirt with check-out girls just for the heck of it? Are you a check-out girl and flirt with sad-looking middle-aged men for fun? Are you Vernon Kay? Tell us about flirting triumphs and disasters

Thanks to Che Grimsdale for the suggestion

(, Thu 18 Feb 2010, 13:00)
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One good, one bad, and two sides of ugly
Good
My coolest flirting moment was meeting a girl from Reading at a college buddy's housewarming in Swindon, where I now live. She was a mate of one of his housemates or something. Helen, I think her name was (it can be that for the sake fo the story, anyway).
Anyway, we clicked straight away and were chatting in the kitchen quite happily. She excused herself to go to the loo, and I let her get about 5 paces away then said, as if I'd remembered something I'd forgotten to mention earlier "Oh, Helen?".
She turned and I had my hand outstretched toward her, she took it, I drew her towards me for a passionate and romantic snog. Inside, I was thinking both "YESS!!" and "Blimey! That was actually quite cool!".
We spent the rest of the evening canoodling in various corners. Unfortunately I didn't pace my drinking, so I ended up getting hideously, spewingly drunk, and tried to put my hand down her tights while we were sitting/lying on the stairs, at the bottom of which were all the friends she'd come to the party with.
We half-heartedly met up a couple of times after that, but my more characteristic cack-handed relationship skills trumped my one-off ace flirting.

Bad
The sister of a girl in my am-dram group at Poly came to see one of the plays I was in, and was being flirted with outrageously by her at a cast party. She (the sister) was intimidatingly attractive, certainly when compared to her rather plain Poly am-dram sibling. She was a couple of years older, too.
To defuse my nerves, I tried to use humour on a subject we had in common. Unfortunately the only thing we did have in common was the plain speccy am-dram sister. I made some weak gag about how her specs looked like the "joke-shop coke-bottle glasses", only to discover she was legally considered to be partially sighted.
It wasn't the end (she actually hung around Brighton for another week or two and took a job at a cafe across the road from my flat), but my fear and embarrassment meant I couldn't ever look her in the eye after that. One of those occasions where, with a time machine, I'd give my younger self a dead arm and say "for Christ's sake, just fuck her!".

Side 1 Ugly
In the first flush of full manhood in late teens and early 20s, I was a skinny, snake-hipped young thing, with cheekbones you could cut paper with and an almost full head of hair.
Met a scorchingly fit Asian girl (I've alway had a penchant for the dusky) at a student party back in 1987. We were both very drunk in that happy, everyone's your best pal sort of a way. I made a clumsy pass, she politely rebuffed, and we carried on happily chatting for the rest of the evening. An odd-looking chubby fellow could be seen lurking on the other side of every room we went into, but I thought nothing of it until much later when he confronted us with a lengthy rant.
"Just because you're so good-looking doesn't mean you can monopolise all the best-looking women", he shouted at me. Which was both hilariously pathetic (for him) and rather complimentary (for me).
Side 2 Ugly
Fast forward 10 years, to my days sharing a house in Acton in my first remotely well-paid job, after years of struggling to make ends meet. My first investment was in pies, which made me somewhat porkier than the girlbait I'd (mostly unknowingly) been at college. One of my house mates was a stunning Sikh girl who I had the hots for big style, but in my callowness "didn't want to spoil the friendship with" (code for "didn't want to risk rejection by making a move, preferring instead to worship her from afar"). With hindsight, she probably felt the same way and was waiting for me to make a move, then got bored of waiting and hooked up with another guy.
She moved out of the houseshare to another out further North, perhaps in part to get away from my moping, but we were still pals and I got an invite to the housewarming. It was fancy dress; not knowing what to wear, I decided on impulse to shave my head, dress entirely in black denim and cowboy boots (yeah, I know!) and go as Yul Brynner. Of course, the effect was more Buster Bloodvessel, and far from realising the error of her ways, my sultry love goddess continued her pursuit of the blond and athletic guy she'd latched on to.
Glowering across the room, getting steadily more drunk, I eventually confronted the "blond, good-looking bastard" for managing to pull someone I'd held a candle for much longer than he'd even know her.
Then heard the hollow, decade-old laughter of a skinnier, hairy-scalped me echoing around the room. It was the only thing anyone could hear, since the party effectively stopped until I had left it. I never did see her much after that. Who says there's no karma?
(, Mon 22 Feb 2010, 13:37, closed)

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