This one cute girl that I talked to occasionally liked me too, and I knew it. So one day I just looked her in the eye and asked for her number. I got it. It depends more on the circumstances than it does the actual guts. The most important thing is to be relaxed (which is easier said than done, but still) because looking at someone through the eyes of fear will scare them, instead of looking at them with the relaxed eyes of love, which is more likely to get through, since it means you are showing an interest in her as a person. I obsess way too much over circumstances, and for that matter, I think about it way too much, when all you have to do is approach her, because she is just as scared as you are, and she has no idea what she wants, any more than you do. For that matter, you probably don't know what you want until you get it, because otherwise you have nothing to base it on.