In the episode, Jack — who has just fallen off the wagon — heads to the bar for a drink after Rebecca (Mandy Moore) leaves for the first leg of her tour. Jack doesn't give Rebecca an appropriate goodbye, something that young Kate chastises him for. When receptionist Heather (Megan West) hits on him while he's out, Jack realizes that he has to go and make things right with Rebecca — despite having one too many at the bar. He calls Kate to thank her for the advice, then speeds off in his car after dropping his keys.