confidently pursue my next relationship

I’m starting to think maybe I should just let things happen instead of pursuing things? I really have no clue what the best approach is here…..

I’ve always just fallen into relationships, when I know someone likes me or there’s not too great of a chance of rejection. But as soon as I get back to school there is a girl I don’t know well, but whom I’m going to actively pursue. If I get rejected, no big deal…but I have to prove to myself that I can put myself on the line when it comes to these sorts of things.