Originally Posted by huno
First off, let me just say that I hear you when you say you feel bad when you compare yourself to guys who can get dates easily... it's especially hard to get over an ex when you don't meet someone you're compatible with.
The first thing you should know is that it takes a lot of searching to find someone you'll really be into. I personally am very picky so it takes me a long time. :) But it's worth it, since I know I'm just not happy dating just any girl I meet. I imagine you're the same way, and I think it's perfectly fine--in fact, probably more healthy, since you don't waste time and energy trying to be with someone you don't really care about.
Yes, some guys have it easy... but they're lucky. That's just the way life is and there's little you can do about it.
In any case, I think any time is a good time to ask a girl out if she's interested. Most will make time for you if they want to get to know you better. She may be hesitant to go out with you because she doesn't know you very well... you might just call back again in a few days. Some people need some convincing.
Or she may not really be that interested, in which case you should just move on to the next one in a week or so.
Ultimately, though, you should know that you can't give up and you shouldn't let it get you down. Yeah, rejection sucks, but you reject girls all the time (you may not even know it!) and so it's really a part of life. It took me quite some time to deal with the sting that comes with being passed up for a drunken frat boy or a vato from east LA, but like physical pain it goes away after a while (why hasn't anyone come up with an ointment for the pain of rejection?).