Dating Dilemma - To Date or Not To Date

Hi everyone! Thanks for coming here to try and help me out!

I've been single for a while. I've been rejected a lot. I really suck with girls. The new school year just started and I don't have any girls in my classes that I could see myself dating. I'm friends with a girl named Hanna and a guy named Jake. I'm friends with both of them. They broke up a week or two ago after dating for like a year. And I'd really like to ask out Hanna at some point (I would've asked her out last year if she was single), but I don't know if/when I should. Any advice?

Thank you to everyone!