5x10 - But Not as Cute as Pushkin
Rory is delighted when the headmaster of her old prep school asks her to play hostess to a young student, Anna, who is thinking of applying to Yale. However, Anna turns out to be more interested in boys than academics and runs off to party, leaving Rory to deal with Logan's elaborate practical jokes. Meanwhile, Lorelai and Luke have their first fight when she accidentally upsets him by buying an old boat that had belonged to his father.
See you in another life, brother...