Not asking out...
But a total failure at being asked out.
Now I myself have never ever chatted up a girl due to my lack of confidence and meek nature. My 'technique' involves a high degree of chance and alot of waiting. If word gets around that a girl I like or get to know through other friends etc likes me, then I go in to full blissfully unaware/friendly male mode, but while still flirting and dropping subtle hints and after a few weeks/months it either peters out and comes to nothing, or the suspense becomes too much for them that they fling themselves at me through sheer frustration.
The advantage of this technique is that the successes tend to be intense and passionate (if not shortlived) and it pretty much eliminates the margin for embarassment. But you do end up going through long dry spells...

Anyway, on to the story...
Cardiff a few years ago, shortly before I got together with my current long term girlfriend. I was out with friends at the now sadly defunct Point venue in the bay. Pretty much a lads night out with no intention of trying anything on with the opposite sex, as it goes against my said 'technique'.
After having consumed more than my fair share of beverages, amongst other things, I was happily sat to the side of the dancefloor taking the lights, people and music in with my friends.
All of a sudden I sight a girl strolling right up to me, I can't remember what she looked like but I remember my loins approved. She straddled me and placed herself on my lap, facing me.
'Hi there'
'Oh...hello' I said bemused.
'I'm having a bit of trouble with my top. Can you...?'
She looks down at her corset and the laces at the front are slightly, neatly undone. Now for many red blooded males this situation would have ended right there with a meeting of the tongues. But for me in my condition and complete inability to grasp the sub-text?
'Uhhh...oh right. I'll see what I can do'
Her bosom right in front of me, I observe for a moment. Then proceed to attempt to re-tie the laces in my extemely inebriated state.
Eventually after much fumbling, I come to the conclusion that my hand to eye co-ordination is not up to the job. I look her in the eyes and smile apologetically...
'I'm sorry, I'm far too drunk. But my friend over there will be able to help you i'm sure'
My friend gives me a look of confusion, surprise and eagerness. The girl was pretty dumbfounded too, if not a little insulted i'm sure.
She gently thrust her chest closer to me, pushing me back in the chair, but there I was with the same moronic, apologetic grin on my face. The girl looks over to my friend, who shrugs and chuckles a bit. Then she gets up and wanders off to her group of friends.
'What a nice girl' I think to myself.

When I had sobered up a little later and the whole thing dawned on me I tried to track the girl down (after maybe the greatest facepalming of my life and much mockery from my friends). But she was nowhere to be found.
But not all was lost! A few weeks later my current girlfriend and I got together and have been happy ever since. I just pray i'm never single again so things like that don't happen...
(Megamoss, Tue 15 Dec 2009, 3:58, 3 replies)

I've done something horrifically similar...
At V Festival a number of years ago, I had been flirting and play fighting with a girl in our camp all day. When it came to evening, she asked if I wanted to stay in her tent, as it was freezing. I offered her my blanket and went to bed.

I felt like a fucking tard.
(The Kwyjibo A big, dumb, balding North American ape., Tue 15 Dec 2009, 9:52, closed)

DOH!
We've all done it. Have a click.
(DownhillGardener no-one does it like that anymore, Tue 15 Dec 2009, 12:11, closed)