they could have sat in the back of some philosophy 101 class and bonded over eye rolls at that one kid in the class that had to have an opinion on everything because there's ALWAYS one in that kind of class. it'd have probably been in sam's sophomore year/rory's senior if that works for you? she was painfully shy going into college and had a roommate her freshman year that sort of dragged her out of her shell so before then she'd have probably been awkward and unresponsive