Your fear of rejection may be overshadowing reality. That's because even one rejection causes a significant ding to your self-esteem. It helps to put rejection in perspective. If you approach a girl and she rebuffs your inquisitive leanings, this doesn't mean you: (a) will be dateless forever, (b) need a personality transplant or (c) really are better off alone. Odds are she's been affected by something that doesn't involve you at all, like a recent break-up. She doesn't even really know you yet, so how could the rejection be personal?
However, a brush-off is easier to take if you're feeling confident about your self-worth. Take a good look at your strengths and positive qualities, and then make a plan to nurture them. For example, if you like to play hoops in the driveway with your little brother, take those skills to an afterschool program for younger kids or volunteer to coach a youth basketball team. Sure, this doesn't seem like it will directly land you a date -- but it's all part of the preparation. If you feel good about yourself, other people will, too. On the flipside, low self-esteem is often accompanied by anxiety. Giving your nervousness the boot may give you the gumption to approach her.
So, when's the best time to approach a girl you don't know? Don't do it when she's with a group of her best girlfriends. They're likely to be protective of her and make it more difficult for you to ask her a direct question. Still, it's a good idea to talk to the group she's in. If it's a boisterous crowd, crack a joke. If the collective vibe is more like a study group, subtle humor will help you make headway. Then, when the girl you like is by herself (it will eventually happen), all this pre-talk will make it easier to strike up a one-on-one conversation. But what do you say? We've got a few openers on the next page.