Jeez, the dating game...
I can't answer any of your questions really, but one thing that does work for me - Don't see women as potential lovers, girlfriends or whatever, see them as friends, be yourself around them. Don't be afraid to flirt a little, because otherwise they'll think there's no fire in your loins :lol:, and besides flirting's fun and good for self-esteem.
The last girl I was involved with, I thought was cute, but she had a boyfriend. But we were together a lot because we were doing a college course together. I don't think either of us saw each other 'in that way', we just had fun - we'd make each other laugh, I would kiss her on the cheek to say goodbye at the end of the evening (as I would for all the other girls, and hug all the blokes), and we found it difficult to curtail our embrace, and then one night out on the beers we ended up falling over in a heap on Oxford St in London while we were clowning around. Somehow, and it wasn't down to my sleight of hand, we ended up in each others' arms, looking into each others' eyes.
For me, the whole 'dating' idea wouldn't work for me, because I think I'm still a little shy in that regard. Building things up as a 'date' would make me worry too much - it would stop me being myself. I don't do idle compliments and tacky gestures [that isn't to say I can't be romantic!]