Most Helpful Girl
Most Helpful Guy
Yep! you have to be the one that makes the move. It's awkward, and you if you're a good person you're going to feel like you're screwing it up the entire time. Welcome to being a guy.
If you're talking about asking a girl out, then you get to make the awkward advances.
If you're talking about making the first move towards sex, then yep, you have to go for her breast first. She's not going to reach for your crotch.
If you want my advice, be bold. The worst she can do is say no, and you'll have to move on.