There is a girl at school that I have been interested in for a long time. We have never really talked much but she seems like a lot of fun, and she isn’t bad to look at either. My problem is that I seem to be caught in an awkward middle-zone where I’m having trouble figuring out how to proceed. I’ll explain.
I don’t know her well enough to ask her out based on a pre-built relationship the two of us have. We’ve talked a few times, but never much. At the same time, we’ve been in each others’ vicinity for almost three years now without anything ever happening, so I can’t really take the “introduction and ask out” approach.
I’ve been thinking about this for a while now and I just don’t see the opportunity to make it happen, but I’d really like it to. I know some will say “just go for it” which I am willing to do, but it does come off pretty weird from someone that’s been nearby for a while but never approached you before. I’d love to go for a more tactful strategy. Any advice is appreciated!
LemonVibe 
How would you like to spend some time would me? (Insert movie here) is playing. A new restaurant just opened.
This is oh so familiar to me. Take the advise I wish wish WISH I could have given myself. Just say it. Either she is interested, or she isn’t. But having it in the air doesn’t improve things and could in fact be picked up incorrectly by her and the last thing you want is to be misunderstood. It’s scary but believe me, you will be much happier with a no then a what if…..so many what ifs……
I understand why you are confused on how to approach her. On top of that, if you are shy, then just asking her out for a movie or something will be even more difficult. I think you should talk to a close friend of hers and ask her if she thinks the girl would be interested. That would help you in two ways. Girls share everything with each other. So she’ll surely find out that you asked about her. If she isn’t interested, she’ll just send the message through her friend. And if she is, then either she’ll approach you herself or atleast now you would know. So you can ask her out without any worries.
Hmm, I think you should at least try to befriend her first. Build up your friendship. You’ll have a better chance of her saying yes if she knows you well.