I'd include some Mary Lou Williams, cause it swings like a M.F., is emotionally moving, and will show her that there have been great women in jazz, too (not a dis to the likes of Norah J., who she'd probably also enjoy, but who have really achieved mastery over the vocabulary of the music). I agree about the Dex ballad, and maybe some Lee Morgan (Ceora, Sidewinder to start(?)). Good luck. I've done this thing with about every woman I've ever dated, and it usually got 'em more interested in jazz.