Boy does that sound familiar.
I used to have a pattern of asking out all the most inappropriate people. I'd really build up a crush, and that way get the nerve to ask a girl out.
-There was the one on whom I didn't see the engagement ring, and whom I asked out in PUBLIC in front of a bunch of people;
-There was the lesbian;
-There was the goth chick who took my love poem I wrote her and read it to all her friends, who laughed at it in front of me;
-There was the paranoid girl who became convinced I was stalking her after I went out with her ONCE;
Those are all the ones I can think of off the top of my head. The others I've probably blocked out to be able to keep living without losing my mind.
If it's any consolation, you are not alone, oh my brother...
_________________
Whatever you can do,
Or dream you can do,
Begin it.
Boldness has genius,
Power and magic in it.
--Goethe