Bailey and Will plan a trip to Mexico, and the girls want to go too. The car breaks down in the middle of nowhere and later the car is stolen. Bailey and Will end up having a fight but they realize that 10 years of friendship is not worth a fight. Kristen's mom is spending a few days with them because her marriage is falling apart. She tells Kristen that Gene discovered about an old affair of hers, and Kristen won't forgive her until she forgives Charlie. Julia runs into Griffin, who got back without telling her. He never answered her letters and she gets mad. He tells her that he's in love with her. Claudia returns from summer camp in love with a boy who everybody thinks it's made up, but he comes to visit Claudia and she gets mad at everybody for not believing in her.

Will is leaving for college and his new roommate comes from Seattle so they can go together. He's a freak, but Will has to be nice to him - after all they're spending a year together. Bailey feels threatened by his presence and they have a fight. Bailey finds his car and decides to live in a dorm to meet people and move on with his life. Will leaves. Kristen gets a job far away and they have to deal with the distance. She tells Charlie that if they were married things might have been different. Julia wants Griffin to find a place of his own, but he spends his money buying her a car. She gets fired after he confronts her boss and decides to leave to San Diego to get on with his life. Claudia wants her relationship with Byron to be just like Julia and Griffin's, but Byron is more interested in Julia than in her. Claudia blames Julia for stealing her boyfriend but later realizes that he's the jerk.

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.

Kristen is getting more and more depressed, and not even a job as Salinger's hostess makes her feel better. Charlie tries to help her as much as he can, but nothing seems to work. He wants her to get better fast and medication can take 6 weeks. Cooper lets Bailey crash in his place. Julia starts to date him and things get awkward between the three of them. Bailey asks Julia not to date his friend, but she decides to date him anyway. Later she realizes how much they don't have in common. Bailey is looking for a new place and finds one cheap with a good roommate, Callie, who Sarah really doesn't like, but Bailey tells her not to worry. Claudia has to find a plumber to fix the pipes and gets yelled at because it costs 3,000 dollars, but she says she's 13 and that was not her job.

Julia moves into the attic now that Bailey is living with Callie. Cooper wants to sleep with Julia, but she's not ready yet, so he threats to break up. She decides to sleep with him but backs off in the last minute, which gets him really pissed. Bailey and Cooper have a fight and he dumps Julia. Callie convinces Bailey to pose as her boyfriend. Turns out his teacher used to date Callie. She tells Bailey that TJ is a psycho and Bailey confronts him, but it was all Callie's imagination. Claudia and Jody are back together. Claudia is sleeping over every night and Jody reveals that her mother's boyfriend is harassing her. Jody is missing and Claudia tells Charlie what's going on, and he tells her mother. Kristen is taking medication, but it doesn't seem to help. Claudia is worried about Kristen and call her parents.

Kristen's parents arrive and Charlie gets furious with Claudia for calling them. Gene keeps blaming Charlie for her condition and threats to sue him. Ellie can't interfere because she doesn't want to ruin her marriage again. They decide to take Kristen back to Chicago, and Charlie tries to stop them, but Kristen is too disturbed to decide anything. Julia and Sarah go to Dartsmouth for their interviews but they can't keep their minds away from home, so Julia realizes it's better to go to a college close to home. Callie is having problems with her father and she and Bailey drink to celebrate their independence. Bailey and Julia decide to go home to comfort Charlie and Claudia can't forgive herself for what happened.

Charlie is angry because Kristen is gone. Grace comes into the restaurant looking for support in her homeless program. She wants the leftovers from Salinger's, but Charlie kicks her out of the place. An old friend of Nick comes looking for a job, and Charlie gives him one because his father used to. Claudia believe that everything bad happening is the house's fault, so she gets an exorcist. Someone opens an account in the name of Nick Salinger, and they think it was the exorcist but actually it was Earl. Bailey tells Callie that the last time he had sex was 2 years ago. She seduces him and they sleep together. Sarah is throwing a Halloween party and Bailey goes so he won't feel so bad for cheating on her. Julia is upset because Justin is dating a new girl and tries to ruin everything, but regrets and get them back together. Bailey has a fight with Sarah and goes to Callie for comfort, but she is with another guy, so Bailey decides to look for comfort in a beer.

Julia meets a Stansford teacher who is also a writer. They become friends and she gets inspired to write. She asks for his opinion and he tells her that she's not good. She is devastated but after she finds out that her mom only chose music after college she realizes that it's too soon to decide what to do for the rest of her life. An old colleague of Diana, Avery Baltus, introduces himself to Claudia and tries to develop in her Diana's talent with the violin. Claudia gets overexcited and Charlie tells her not to hurry, she still has her whole life ahead, but she is stubborn and decides to enter the conservatory. Bailey has the chickenpox and Sarah is taking care of him, but he doesn't want to. They have a fight, but Sarah loves him too much to stay mad at him forever.

Charlie has a slogan contest at Salinger's and the winner wants to bring homeless people to have dinner at the restaurant. Charlie has to kick them out so his clients won't leave and Grace prints in the paper what he did, giving him a hard time. They have a discussion and after Grace admits being wrong about him they come up with a solution. Sarah is worried because Bailey is drinking too much, but he says he's only celebrating. He tries to get in the hockey team but he's not in good shape, so he gets invited to the wrestling team, which is the worse in school. He doesn't support Sarah's new job and they have a fight. She says he's changed. Julia is having problems with the roofers. Alec offers her pot, and she turns it down. She talks with his brother and he fires him. They flirt. Claudia tries to get back at Charlie for not letting her go to the conservatory.

Bailey saves Callie from being raped. She is scared of going out of the house and Sarah tries to be her friend and wonders why she doesn't have many female friends. Charlie is helping Grace. He worries about her safety because she lives in a dangerous neighborhood. She tries to kiss him, but he tells her that he has someone - Kristen. After Sam gets fired for not covering the roof, Julia rehires him from her own money. He discovers her lie and she kisses him. Claudia is offered a column in the school paper about heart stuff and she soon realizes that something's up with Bailey. Callie tells him that she wants someone like him.

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.

Charlie decides to go to Chicago to see Kristen and leaves Julia in charge. Kristen is very happy to see him, although Ellie is not. She tells him that she wants to run away to San Francisco, but half way there she realizes she's not ready to go back and they return to Chicago. She says he's her problem. Charlie leaves her there. Julia is more concerned about her personal life than her brother and sister. Claudia claims to be sick, but Julia won't believe her until she gets a call from the hospital saying Claudia had appendicitis and had a surgery. She won't forgive Julia until she overhears how sorry she is. Bailey lies to Sarah in order not to sleep with her. He skips practice and Sarah finds a drunk Bailey passed out at his place. He tells her he slept with Callie, but they don't break up. Callie is tired of being used by Bailey.

It's Christmas. Jake comes back. Charlie decides to get rid of all Kristen's stuff left so he can finally move on with his life. He tries to help a homeless man at the restaurant. Sarah and Callie are away for the holidays and Bailey wants to spend it all by himself, but Coach doesn't let him. Julia notices that Jake can't see very well and he tells her he's going blind. Charlie sees him leaving and Jake says he has to go for his chemotherapy appointment. Julia asks Bailey to spend Christmas in the house and he brings Coach with him since his daughter is not coming anymore. Stuart gives Claudia a very expensive gift and she tries to give him a bad gift, but he loves it. She tells him that she doesn't like him in that way, and he gets mad, but apologizes and stay over for Christmas dinner. Grace shows up and Charlie invites her to stay, and they all celebrate Christmas.

Libby, Julia's old friend, killed herself. Justin and Julia feel like if they paid more attention to her she would be alive. Her death makes everybody wonder what they are doing with their lives. Sarah realizes that life's too short to spend it with a ruined relationship so she decides to break up with Bailey. Meanwhile, Charlie is having some friends over for his high school reunion. He misses the good old days, but the truth comes up and he realizes his life wasn't as good as he remembered.

Bailey is very excited with wrestling and wants to tryout for All Stars. Although Coach Petrocelli doesn't think he is able, Bailey gets obsessed to win. He wants someone to be there for him, but Callie is mad at him and wants him to move out, and everybody else is busy, but Claudia, who misses him at home. Bailey celebrates every victory with a few drinks, and every time he gets more and more drunk. Julia finds out that Sam was engaged and she joins him in his dinner with his ex-fiancée. She is getting married and he realizes he still loves her. Charlie gets an award for helping the homeless and realizes how much he likes Grace when another man asks her out.

Bailey is not doing so well in school. Callie throws a big party at their place and the landlord threats to kick them out. He is trying to stay sober, but it's hard. Unable to keep up with school, he decides to quit. Charlie doesn't want to rush things with Grace, but the more they try to slow it down, the more they want to be together, so they sleep together. Julia is accepted in Stansford, but is not sure she wants to go. She wants a time off studies, and to find herself. Charlie thinks it's all Sam's fault. Ross is dating one of Claudia's teachers, and she outs him to the entire school. She tries to fix it, but Ross tells her it's not that easy.

Will surprises Bailey showing up at his place. Will thinks Bailey drinks too much, and asks Sarah what's going on, but she doesn't want to talk about Bailey. He tries to advice Bailey about his drinking, but Bailey says it's no big deal. Callie asks him to move into her room. Grace's place burned down, so she moves into the house. Charlie doesn't want Julia to turn down Stansford. Julia, angry with Charlie, moves to Sam's so she won't have to listen to him. Charlie doesn't want her there, and they have a big fight. Sam tells Julia she should go back to the house. Claudia tries to get Bailey to help, but he ignores her.

Bailey is spending so much money on drinking that he can't even afford rent. Julia wants to get Bailey and Sarah back together, but she's still very mad at him. She warns Julia about Bailey's drinking problem, but Julia doesn't believe it. Julia gets Bailey a job with Sam. Bailey steals expensive liquor from the house he was working. Julia wonders if what Sarah told her is true. They try to talk to Bailey about it, but he won't listen. Taking advantage from Julia and Charlie's fight, Bailey gets Charlie to support him. Julia and Claudia don't like Grace. Charlie tells Claudia she should try to be Grace's friend, and so Claudia offers to volunteer at her program, but that doesn't last long. Grace can't stand the kids. Charlie wonders if Grace really wants to be there.

Grace's parents are spending time with them, and Grace doesn't like it, but Charlie does. Claudia is spending time with Avery, which makes his son jealous of her. Bailey spends all his money in drinking and can't afford a clown for Owen's birthday party, so he dresses as a clown. He gets to the party drunk and ruins it. Martin tells Charlie that Bailey might have a drinking problem, but Charlie refuses to accept that idea, even though everybody else thinks so too. Julia breaks up with Sam because he's a racist.

The Salinger family tries to solve Bailey's drinking problem. Claudia calls him and tells a story about Owen falling down the stairs. Bailey rushes to the house, when Charlie, Julia, Claudia, Grace and Sarah hold him. One by one, they all try to show Bailey that he has a drinking problem. He refuses to accept it and fights with everybody. Joe arrives and tells Bailey that his father had a drinking problem too, but he stayed sober 18 year until he died. Bailey doesn't believe it, but Charlie does and proves to be true. They all try to get Bailey into an AA program, but he refuses. When everybody had already given up, Claudia tells Bailey that if he doesn't face his problem and look for help, than he will no longer be a part of the family. Bailey leaves.

Bailey is alone. The Salingers strategy to not speak to him doesn't seem to be working. Bailey keeps drinking and drinking, and he misses his game. Coach Petrocelli gets really disappointed at him. Bailey can't stay sober. He tries to have sex with Callie, but she tells him that he really has a problem. Claudia goes to Avery searching for answers for questions about her father. She blames Bailey problem on her father, but Charlie tells her that he got over his drinking problem, and became a wonderful father, as she knew him. Griffin comes back and Julia spends the night with him. Bailey picks Owen at the daycare and disappears with him. When he gets to the house, Charlie kicks him out, and Sarah goes after him. She tries to talk to him, but he doesn't want to. They get on the car, and Bailey crashes it, hurting Sarah. At the hospital, Bailey cries and asks Sarah for help.

Bailey starts to go to AA meetings, and on his first meeting he bumps into Walter Alcott, the man that killed his parents. Bailey has second thoughts about going to the meetings, and he quits. Griffin gets US$100.000 from his lawsuit settlement, and decides to help his father, and he becomes friendly with Griffin just for the money. Grace decides to run for council and makes the Salinger's house her campaign headquarters.

Bailey is sober for a week. Callie gets jealous because Bailey is spending much more time with Sarah than with her, so she tries to help Bailey, but she can't. She goes to Sarah and tries to find out why Sarah is helping Bailey so much. Sarah tells her that she doesn't love Bailey, because she has a new boyfriend. Callie gets drunk and Bailey moves back to the house. Julia starts skipping school in order to hang out with Griffin, and she starts to get F in history, but he tells her to go back to school, and she goes. Claudia is convinced that Grace doesn't care> about her and Owen, so she makes up a story about a reporter just to spend some time with Grace. But she is more concerned about the reporter.

Claudia is invited to play in L.A., and nobody can take her there, but Bailey. They go and Claudia kicks him out of the rehearsals because he is distracting her. In the hotel room, Bailey has nothing to do, and he really wants to drink. He calls Sarah, but she isn't at home, he calls Charlie, but he isn't at the restaurant. So he can't resist and drink, and forget to pick up Claudia. Joe shows up and find a drunk Bailey. He and his wife pick up Claudia, who is very disappointed at Bailey. In the way back, they pass by an AA meeting, and Claudia tells Bailey to go and he does. Grace is really sick, and she may be pregnant. But when the results arrive, and she isn't, Charlie is sad, and when they talk, Grace tells him that she doesn't want to have babies. Julia decides to travel with Griffin all the way to Nevada, but the motorcycle breaks and they have to get back to San Francisco to get it fixed. Griffin decides to buy the repair shop.

Sarah dumped her boyfriend. Her mom tells Bailey that she got into Brown, and Bailey gets mad at her because she is moving away, but she is going to Berkeley instead. They kiss, but Sarah tells Bailey that she just wants to be friends with him. Charlie and Grace break up because she doesn't like children, and she wins the election. Justin is going to Europe for 2 months and ask Julia to go with him. But she doesn't and gets married to Griffin. Charlie, Bailey and Claudia give Julia their mom's ring, and she moves out.