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.

Sarah and Bailey host a Christmas party, while Charlie decides to go on a long distances trip with Kirsten. Will realizes that he and Bailey are living in totally different worlds. Julia pains a nice picture inspired by Justin.

Ned does his best to keep Julia by himself during the holidays. Daphne's irresponsible mother visits and Daphne realizes just how much she is like her. Bailey has teach him Owen that stealing is wrong.

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.

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.

The release of the drunk driver who killed their parents divides the family.

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.

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.

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.

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.

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.

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.

Charlie's infidelity jeopardizes his relationship with Kirsten; Bailey's preoccupation with Kate angers Claudia.

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.

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.

Bailey and Kate disagree over sex; Charlie sets out to impress a potential employer; Claudia's success goes to her head; and Julia struggles in school.

Kristen and Charlie sleep together. Later, she is cold to him and tells him that she slept with him because she is sick and scared. Bailey plans a trip with Kate. Her father wants to send her to a boarding school in Connecticut, but Bailey finds out that she is wants to go. They fight and Kate tells him that she will have sex with him, but he refuses to because she doesn't mean that. Julia and Morgan go on a date. Nina tells her to be mysterious, surprising and make him jealous. Claudia overhears their conversation and do all that to get Arnie's attention. Charlie tells Kristen that he loves her and will be there for her. She tells him that she can't have babies.

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.

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.

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 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"".