Bailey meets Jill Holbrook, a pretty waitress who he falls for and ends up sleeping with her. Morgan begins to drink after his club is closed down and he is forced to pay a fine. Julia wants to help, but he doesn't accept her apology or her money to pay the fine. Claudia receives her first period. Kirsten's family wants her to return home to Chicago.

Claudia spends time thinking about converting to Judaism. Julian finds her mother's old journal and finds that her mother planned to have an affair with another man. In the meantime, Kirsten moves into Charlie's room and gets under a fight with Julia.

Charlie tries out how Kirsten's relationship with Ben Atkins is. Julia is surprised to find out that Justin is dating Libby Dwyer, her friend. Claudia's relationship with Artie is in big question when she take over his role in ""Oliver"".

After an earthquake, Claudia and Jill start acting weard, escpecially Jill. Charlie is suspicious about Jill's behaviour and he's convinced that the main problem are drugs. In the meantime, Julia's friendship with Libby is again shaken because Justin.

Jill has a car crash and Bailey thinks she might be on drugs. Julia and Justin tell his mom that they're going out. Justin gets mad at her for spending too much time with his mom, and she tells him how much she misses a mother to talk to. Arnie's parents are breaking up, and Claudia makes a plan to get them back together, but it fails. Charlie tries to be a better father for Owen, and the baby says ""dad"" to Charlie. Bailey goes to Jill's mom for help, but she doesn't care. Jill is missing and her mom goes to Bailey for help, apologizing for her previous rudeness.

Bailey urgently travells to L.A. to find missing Jill. In the meantime, everyone is too occupied with Claudia's 12th birthday. Julia spends some time with Danny, a male who is HIV positive.

Bailey gets into big doubts, when Kate, who has returned back, and Jill both want to get back together with him and continue their relationship where it stopped. Charlie becomes troubled when he grounds Claudia and does not gives Bill a raise. In the meantime, Julia wins a award for her writing, but she's not in the bad mood, because she humiliated her siblings.

Bailey interferes in Jill's business when she decides to take over of preparations for a school dance marathon. Julia does not wants to rush into having sex with Justin. Charlie realizes that he needs his family now more than ever, so he's in doubts about leaving the house.

After Jill dies because of overdosing, Bailey refuses to believe that she's dead. In the meantime, Griffin Holbrook; Jill's brother; comes in and does not wants to have any business with Julia, so he trie to avoid her. Finally, Charlie and Kirsten get engaged.