>The odd thing is I'm not just afraid of getting rejected, I think I'm also afraid of her liking me back. I think "What if this works and we start going out just for her to realize I'm boring."
I have that same fear. I don't know which I fear worse. All I can say is to live in the moment and not focus on the future in this instance. No sense in speculating if nothing happens, right?
>I've had enough bad luck with romance and I think it my be my turn for once.
I also feel this way, but don't let it turn into a sense of entitlement. That will get you nowhere.
Good luck.