S2, E19: Luke asks Rory for help after he learns that Jess is failing several high school classes. However, during their first study session, Jess convinces Rory to let him drive her car, and he crashes it, breaking Rory's wrist. Lorelai becomes furious at Luke for putting Rory in danger by encouraging Jess to study with her, prompting Luke to put Jess on a bus to New York.