Well, once it gets to that point I'm sure Simon can handle himself well. This thread, was more about HOW to get to that point. Personally, I'd just go for the aggressive approach, just ask her if she wants to hang out sometime, if she says no, then hey no big deal suck it up and move on. Finding the correct time/place can be tricky, you just gotta do it when the time feels right. If shes on the school bus with you, then that would be a good place, if not then try and catch her before or after school. Or, like if you know shes hangin out at the mall, or the library, on a certain day, then try and arrange an ACCIDENTAL meeting, that has worked for me in the past. Remember, its all about being confident, and acting like your interested in her.