Your main problem seems to be conversation. I had great difficulty with that one (until recently). This is going to sound cliche, but the only thing you can do is practice.
Here's a good excersize to try out. Go into a clothes shop, into the womans section, find a hot assistant and tell them your buying clothes for a girlfriend of yours, ask her whats in style and ask her to pick some clothes out (you don't have to buy them), then just drop something in like "she's in need of new clothes, she's going on holiday, to!place! and shes really excited, it supposed to be really nice", then ask her if she's ever been. She'll talk for ages. don't try for a number close unless you feel 100% that she will say yes. after all, this is practice.
The thing with conversation is that get them on the right topic and women ramble on for ages. For instance i got one girl onto holidays, she couldn't shut up for 10 mins!
If she seems short. So what? Leave. practice on some-one else until this conversation thing is as easy as jerking off.