I dont know how open you are to this idea but you could always try an online dating site. A lot of people dont like them, but you can meet some nice girls that way. My brother is a nice guy with a good job but he just didnt have the confidence to pick up girls. He has a really nice girlfriend now and he met her off one of those sites. Even if you don't find the girl of your dreams this way, you could get the experience and confidence needed to ask out someone you may already know and be attracted to. Good luck.