S5, E10: Rory is delighted when Headmaster Hanlin Charleston (DAKIN MATTHEWS) from her old prep school asks her to host a young student, Anna (SARAH FORET), who is thinking of applying to Yale. However, Anna is much more interested in boys than academics and runs off to party, leaving Rory to deal with Logan's (recurring guest star MATT CZUCHRY) elaborate practical jokes. Meanwhile, Lorelai and Luke have their first argument when she upsets him by buying an old boat that had previously belonged to his father.