[It probably does come across exactly as he means it, but Kat is susceptible to praise and anything that sounds like it, and she latches on to that compliment because it brightens her right up.]

So, hanging out with me hasn't been too much of a drag for you?

[(He could just be shy like the others... but I think he's just being friendly. Yeah, of course he is.)]

You seem pretty reserved normally, but you actually pay attention to people when you're around them, don't you? [She places her hands beneath her chin.] Maybe I'll be even more likable once we give this a shot?