The Salingers face with their most difficult obstacles since the death of their parents when Bailey's (Scott Wolf) college partying escalates into a serious drinking problem. After a family-planned intervention and the disclosure that their father was an alcoholic cannot persuade him to seek treatment, only seeing Sarah (Jennifer Love Hewitt) in the hospital following an accident he caused sends Bailey to his first AA meeting.
Kirsten's mom arrives to stay with the Salingers as a male bonding adventure exposes differences between Bailey and Will; Julia is surprised by Griffin's sudden appearance, and Claudia returns from summer camp with her first boyfriend.
As Kirsten's new job strains her relationship with Charlie, Julia questions her rekindled romance with Griffin; Claudia faces the loss of her new boyfriend while Bailey sees Will falling under the spell of his new college roommate.
As Bailey succumbs to the temptation to cheat and Julia stumble upon Justin's revealing scholarship essay, Kirsten gets some bad news about her doctoral dissertation.
As Charlie watches Kirsten grows ever-more depressed and Bailey's new roommate upsets Sarah, Julia's relationship with Cooper has its ups and downs.
As Callie's busy love life causes problems for Bailey, Julia considers resuming a sexual relationship; Claudia's best friend reveals a terrible secret while Kirsten's depression takes a toll on Charlie.
As Kirsten's parents arrive to take over the care of their daughter, the Salingers draw together to protect Charlie.
As Claudia turns to supernatural to help the family, Bailey has a sexual encounter with Callie, and Charlie hires a drifter at the restaurant.
As Bailey's battle with the chicken pox exposes his affair with Callie and Julia is stung by a college professor's assessment of her work, Claudia falls under the spell of her mother's musical colleague.
Charlie's treatment of some homeless customers sparks a boycott of his restaurant as an aimless Bailey seeks direction on the school's wrestling team.
Bailey becomes Callie's confidant after rescuing her from a date rape; Charlie tries to keep from being drawn into a new relationship; Julia goes out on a limb to keep Sam from being fired.
The anniversary of his wedding disaster hits Charlie hard; Sarah decides to use sex to revive her flagging relationship with Bailey.
With Charlie in Chicago to see Kirsten, Julia tries to slip off to be with Sam; Bailey tells Sarah the truth about his relationship with Callie.
The Salinger's grandfather Jake makes a surprise appearance at Christmas to find that all is not well at home.
A high school reunion reveals some long-held secrets in Charlie's past; a friend's suicide causes Julia and Sarah to reexamine their own lives.
As Charlie finds he's attracted to Grace, Julia faces difficult choices in her relationship with Sam; Bailey finds unexpected success at wrestling.
Julia makes an unexpected decision about college, as Claudia exposes a gay teacher; Charlie and Grace struggle with their a new relationship as Bailey attempts to keep from being thrown off the wrestling team.
A fire lands Grace at the Salinger's just as Julia moves out to escape a domineering Charlie; Will arrives home unexpectedly to find Bailey's been drinking too much.
As Grace grows uncomfortable staying at the Salinger's, Claudia tries to make help by volunteering; Julia and Sarah team up to stop Bailey's drinking.
Bailey's drinking disrupts Owen's birthday party; Grace bristles at the arrival of her parents; Julia suspects Sam of harboring racist views; Claudia offers to help Avery's teenage son feel more at home.
The Salingers band together to confront Bailey about his alcoholism.
Bailey's drinking endangers Owen and puts Sarah in the hospital; Griffin returns to find Julia's situation has changed; Claudia blames their late father for all the family's problems.
A big insurance settlement leads Griffin's father to ask for money; Grace decides to run for office; and Bailey encounters the unexpected at an Alcoholics Anonymous meeting.
As Grace's campaign continues to create havoc at the Salingers, Bailey decides to move back home; Julia's lax attitude about school concerns Griffin, while Sarah meets someone new.
While chaperoning Claudia in Los Angeles, Bailey resumes drinking; Charlie discovers Grace doesn't want children; and Julia must decide whether to help Griffin realize a dream.
As Julia is invited to spend the summer in Europe with Justin and Bailey learns Sarah is going away to college, Charlie's relationship with Grace is tested by her unwillingness to have children.