It's not about whether someone is "in your league" or "out of your league", it's whether you can convince them to join your team.
Now, onto a slightly different but somewhat related subject.
Lately, I've been wondering why people don't just go on dates. If you're interested in someone, shouldn't you just take them on a date, get to know them, and consider the potential? What's all this about hanging out and becoming friends before you take them even on the first date? And, really, what have you got to lose from one date?
Men, I challenge you. (Women can take me up on this also, but it's less your responsibility)
Here's the challenge. If you see a girl that you may be interested in, ask her on a date. None of this waiting for her to show some interest first. Take the risk that she'll turn you down and ask her. Worst case scenario? She says no, and without playing all the silly games, you already know that she's not interested and you can move on!