Jen helps Dawson go back to the psychiatrist, Dr. Rachel Weir, whom he ran away from. Dawson still thinks that the whole idea of sharing his thoughts with a complete stranger is weird, but he is surprised with how much he learns from it. Back home in Capeside, Dawson has to handle the problem with his father's will, which does not include baby Lily. Meanwhile, Joey is working on a project with Professor Wilder about old love letters written by an obscure writer, and with a little help of Audrey's audition videotape for "The Real World: Ibiza," she manages to catch something not one of the fellow students caught. Also, Pacey confronts Karen about the risks she is taking for having an affair with Danny, but she refuses to listen to him. Later, Karen is hurt when Danny's wife shows up at a dinner party the restaurant holds, and he completely blows Karen off.

In Los Angeles, Dawson visits Audrey at the rehab clinic where he spots a big time film producer, named Toni Stark, and follows her into a therapy session hoping to talk to the woman who'll direct Dawson to better contacts. Meanwhile, Pacey throws a party at his place to celebrate his new success at his job as well as purchasing a new super-sized TV set and is surprised when Joey, still sulking over the departure of Eddie, lets loose by getting drunk and setting up a spontaneous game of spin the bottle. Jen catches the reformed alcoholic C.J. with a drink which leads to them arguing, and making up by having sex for the first time. Also, Emma tries to stay in the country to get her green card by courting a stoner to marry her until Jack offers to marry Emma. But in the end, Emma decides that it's not worth it and decides to leave.