She's a tough, defiant person as far as he can tell - something he finds kind of admirable/impressive (and you can imagine the thin, condescending smile that comes with this) in his better moods, and more annoying and foolishly bold otherwise. Simply, he sees a lot of himself in her. That's what draws him to someone he might otherwise have never spoken to. It's not his intent to try to get her to change.
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