I am becoming increasingly confused with how how to handle a girl that I know. I met her a couple of years ago when I started school. She has a heart of gold, and she's a cutie too. I asked her out about a year ago, but she was already seeing someone, so nothing ever came of that.
Fast forward a year: we're still decent friends (I'll hang out with her on occasion, and I see her at school quite a bit). I still care deeply about her, and with her being currently single, I'd love to ask her out again.
There are, of course, a couple of issues that complicate things. First off is that her last boyfriend, although obviously able to charm her also made her cry during dates. They dated on and off until earlier this year, when he broke up with her about a month before one of her major school exams (where major means failure = kicked out). Friends with better girl-reading powers have hinted that she needs time to be single and find herself again, implying to me that she's still recovering from her last breakup, and hence does not need a new boyfriend right now.
The other issue stems from her performance on the major exam. The school gave her a year to take classes, with the ultimatum "pass these classes or goodbye". Most of her friends and labmates have been offering to help her prepare for classes and study. However, I seem to have become her tutor by default.
While I can't complain about tutoring a pretty girl, I'm more than a little worried about what would happen if I asked her out again and she responded negatively. Of the least harm would be if she felt awkward around me and found someone else to help her. But the worst case scenario would be creating a giant distraction from her studies and jeopardizing her career. That would put me in the same league as the last guy.
Do I stand a chance at coming out of this situation with my sanity intact?
I think you're making a few assumptions here that are causing you to be confused.
To start, you seem to think that asking her out means you will have a relationship. It will not. You also seem to think that your friends with "girl-reading" powers actually know what is going on inside her head. Unless she talks to them, they do not know anything.
I admit, this is a tough situation. You stood up and got rejected a year ago, and still pined for her. Now she is having some other things go on in her life and you're assuming she can't take on a relationship too.
But don't assume that you asking her out is going to distract her from her studies. You're the one who is helping her out with her studies. And that complicates things.
Since you waited a year, I think it's fair to assume you're over the moon about this girl. She's available. In a normal world, you would ask her out.
If you haven't already, start romancing her a little. Bring a snack to your tutoring sessions. See if she wants to get coffee after class to talk about what went on. Bring her favorite bottle of wine to dinner. And then ask her out, no strings attached. If she's interested, she will say yes. If she's too busy, she'll tell you that. If she doesn't want to date you even when she's single, at least you have a close friend.
No matter what the outcome, you can get your love life started again and stop waiting for the right moment.