Oh we've all been there. I was cripplingly afraid to talk to girls until I was 16ish, when I basically stumbled into my first relationship in high school.
Definitely been in debt (never more than 7k, but that's what working during college did for me) and it sucked. Totally blows when you put all that work into something people basically require and then you don't get hired anywhere right away.
Honestly with girls it's a lot easier if you start asking them out before you get too close. You don't psych yourself out because if they reject you it's not like you'll ever see them again. (I used to liken it to impressing soloQ teammates, I don't care if I pissed them off because they're gone in 40 mins anyway). And honestly dating is all about getting to know people anyway, just like friendship...except with sex and stuff. But when you meet someone cool, ask them either out or for their number before you part for the first time. If it's the number make sure you ask her out within 2 days. If you put a hard timer on it you won't do the forever-pusing-it-back-into-the-friendzone thing.
Not that I'm the VHL's authority on women but I've been described as someone who "has wheels" by Noah Lefevre...so I'm pretty sure I'm legit.