Hmm. Worth considering. Though, stuff like that isn't all that exciting - at least not for him. With that in mind...
"So, hey, since we're kinda already doing it, wanna hang out like officially? Cause you're pretty hot and that's my thing."
It's probably high, he won't underestimate. But he doubts it's enough that she could take anything from the inside of a jacket he's actively wearing.
...Not that it matters, given the jingle of the keys that he can hear when he moves.
"So you say. But you know... I been around for a while and only one person I ever ran across was ever close to half successful at taking something of mine."