Ok guys here's the battle plan.

On [next day she stays afterschool that i know of] afterschool at approx 1500 hours me and two other units approach said female. They will already be accompanied by her and will be guarding her flanks while I approach them for a friendly conversation. As I approach, I notice her, and through a system of inconspicuous motions order them to take the vanguard, while I approach the target female, I will approach from the front, try to get at an even level with her (she's 4'10" and I'm 5'11") without looking awkward. At that moment in time I shall begin to converse with her, while I inconspicuously order my friends to withdraw to another hallway. At that point, I shall ask her if there are any good movies that she knows of that are out/coming out, and when she says yes (if she does, if not see backup plan) sound interested in that movie and ask her if she will accompany myself to that movie on saturday or sunday. If I receive a postive response thank her and continue to converse with her, while inviting my friends back into the conversation. If she says no, go meet my friends in the hallway, after bidding her goodbye, and continue to move down to nearest pizza place to eat away my sorrows.
*Backup plan: if there are no movies, ask her if on saturday she would like to grab a bite to eat with a few of my friends (who will attempt to bring their latest catches). After that, approach her slowly and tell her the way I feel about her. If a positive response is given, rejoice with freinds later. If negative, return to pizza place to get more food.

Any flaws?