At your age, girls aren't gonna make the first move. So yeah, it's up to you to approach them.

Confidence is key. You obviously have a lot of self image issues. You worry about how you look, you're 'afraid' of approaching the girls, feel uncomfortable with your finances and home situation... now just because you're not SAYING those things to the girls, it shows. If you act like you don't care about those things around the girls, they'll be more receptive to the possibility of dating you. Chicks aren't as physically driven when it comes to dating. It's more personality. And confidence is a HUGE thing they like to see in a guy.

Put all those worries behind you and HAVE FUN. Being a worry-wart and meek about things won't get you anywhere.