Great suggestions everybody! My anime veiw is kind of narrow (shoujo mostly) and even though I've seen most of the shows you've all mentioned I never would have connected them to this. Here's what's come up so far:
Lain, Sailor Moon (Ami, Luna), Hand Maid May (Kazuya), Boogiepop Phantom (ep 5), Full Metal Panic (possibly ep 8), Yami No Matsui, Read or Die, Cowboy Bebop, Mecha Shows like Gundam Wing, Macross, Robotech, X (Satsuki), Noir, Excel (ep 5), Dual!, Gatekeepers 21, Digimon, Bubblegum Crisis, Iria, OMG (Skuld), and Blue Seed
I'll have to go through and see if I can find scenes that fit, as Zalas pointed out, even if they're on the computer they may not fit the situation (though that could be funny too). So please keep the suggestions coming.
A question for those suggesting Satsuki from X...So far I have sucessfully avoided the angst that is X, is he really that ideal a character for this? I'm really not familar with him at all.