Bailey tries to impress Kate's father; Charlie balks at the constant comparisons with his own dad.

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.

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.

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.

Claudia feels out of place in junior high school. Will, along with Bailey, checks out an Eastern college. Julia and Justin take action to a new rule that prohibits kissing in school and they organize a protest to convince Principal Stickley to change the rules. Charlie tracks down Pamela. It turns out that Spencer isn't Charlie's son at all and she was desperate for money. Kirsten wonders if he'll be happy with her, knowing that she can never have children. To reassure her, they decide to adopt Owen.

Kristen's parents arrive suddenly to spend some time with them. They're staying in the house, and they drive Kristen crazy. Charlie tells her that she is like her mother, and she says she's not. Ellie tells Charlie that he's just like Gene, a dreamer, but he says he knows exactly where he is. Claudia doesn't like Griffin, so he tries to win her heart. Julia gets jealous and Griffin tells her that he misses a little sister, while Claudia develops a crush on him. Bailey gets 900 points at his SATs and his teacher offers him private lessons, flirting. He takes it again and make the same points. Charlie tells him how it was when their parents were still alive, so Bailey decides to apply for college, writing about his mom in his essay.

Bailey meets a guy at his first day of college. This guy convinces Bailey to take easy classes so he can take good grades and have time to have fun. Bailey faces a very difficult computer test and finds cheating as the only way out. Sarah, Julia and Justin are seniors. They're all competing for a writing competition that gives a college spot. Sarah and Julia are writing about their family dramas and Justin decides to write about Julia's pregnancy, which makes her really furious. But Justin doesn't have to take care of her anymore so he decides to stick to it. After Kristen's boss discovers that she copied her essay from a book, Charlie decides to help her and accidentally finds her anti-depressives prescription. She took it after the wedding. She loses her PhD and her job.

Joe is getting married, which reminds Charlie of his own wedding. If he and Kristen got married, they would be celebrating their first anniversary. Charlie asks Grace to the wedding, but she gets confused when he makes a speech that is definitely about Kristen. She tells him to make decisions about his life. Sarah wants to fix Callie with her cousin, but Callie turns it into a double date right away. She feels like Bailey and her are getting apart, and she decides to sleep with him, but Bailey can't do it. They promise to give it another try, but Bailey sleeps with Callie again. Sam doesn't want anything with Julia and Claudia says she's pathetic, but Julia insists and Sam decides to go back to the house.

When Charlie can't take care of him, Bailey takes Owen on a camping trip. Kirsten and Paul talk about adopting a baby. Daphne is still having hard time trying to take care of Diana. Ned convinces Julia to move into his room, but when Maggie talks her out of it, he hits Julia.

Charlie and Bailey continue to fight over Owen's custody while Owen's learning disability grows. With Maggie's help, Griffin whisks Julia away from Ned to convince her to leave him.