if nothing else he'll know her via ~gilmoregirls, they do food nights, movie nights, etc. she's really easy going, if she knows he doesn't mean anything by his jokes (and i figure by now she'd know that) she'd have no problem with them and probably laugh at 95+% of the jokes. she's definitely not the thrill seeker but if he wanted to go bungie jumping she's the one recording it for later. i'm definitely down for good friends! could be even from childhood if that works