Jake uses his reward money to purchase Shooters. When Jake drops off some papers at the design firm, Chris mistakes him for a deliveryman and makes a lewd comment about Sydney. Chris denies the allegations. Jane lashes out at Jake, and fires and evicts Sydney. Jake gives Syd a job at Shooters so that she won't have to return to the mental hospital. Chris tries to attack Sydney. Michael and Kimberly are asked to appear in a coffee ad. Peter agrees to allow this in order to impress Amanda. She goes out to dinner with him. Billy takes a liking to Alison's college roommate, Susan. Susan moves in with Alison when a chef job in Santa Barbara falls through.

Jake provides Sydney with refuge after learning of the attack. Amanda reveals that Jane and Chris have gone to Las Vegas, and Sydney realizes that Chris is planning to make good on his promise to marry Jane. Michael fears that Chris is after Jane's money. He follows them to Las Vegas, with Kimberly in pursuit. Chris wins big in the casino and proposes to Jane. Michael and Kimberly break up the wedding, then tie the knot themselves. Michael is fired for skipping work. Jo is hospitalized with an ulcer, and Kimberly provides comfort. Jake beats up Chris and sleeps with Sydney. Peter continues to pursue Amanda. Alison learns about Billy's involvement with Susan.

Sydney plans to leave town to avoid her problems with Chris, but Jake convinces her to stay and give their relationship a chance. Alison claims to have accepted Billy's relationship with Susan, but begins hitting the bottle. She gets into a catfight with Susan at a client party, prompting Susan to move in with Billy. Michael asks Amanda to manipulate Peter into rehiring him. Amanda agrees, provided that Michael surrender his share in the design firm. Jane promises to give Amanda 25 percent of the business if she can arrange this. Once Michael has returned to work, he backs out of the deal and tries to blackmail Amanda. Peter encourages Amanda to seek control of D&D. Matt learns that Jeffrey, an ex-lover, is back in town. He is stunned when Jeffrey reveals that he has left the Navy and is HIV positive. Jo prepares for the custody trial.

The trial to determine custody of Jo's baby begins. The Carters' attorney raises many doubts about the character of Jo's friends and neighbors, but Jo shines on the stand. Kimberly learns that she cannot have children because of injuries suffered in the car accident. Alison gets drunk at a client party and leaves with a hard-living music business scout named Zack Phillips. Bruce suffers a heart attack while dancing at the event, and Peter suggests that Amanda use the opportunity to seize control of the agency. Alison is unable to testify on Jo's behalf because she is stoned following a night of partying with Zack. The judge awards custody of the baby to the Carters. Matt questions his relationship with Jeffrey due to the illness, but the two decide to commit to each other.

Zack encourages Alison to buy an expensive new car and skip work. Billy and Susan confront Alison during Thanksgiving dinner, but she reacts angrily and storms out. A drunken Alison tries to drive to Zack's house, but he is having a party with his friends. While distracted by her phone, she crashes into a boy on a bicycle. Kimberly explores several motherhood options, some of them illegal. She invites Jo over for Thanksgiving and convinces her to fake a miscarriage and hide her baby from the Carters. A mobster's associates begin harassing Jake. Sydney is told that Jake will suffer a serious accident unless she sleeps with the mobster's friend--Chris. Amanda leaks information about Bruce's health, while Peter prepares a takeover attempt. Matt and Jeffrey refuse to come to Thanksgiving dinner after Matt's parents ask them to hide the true nature of their relationship.

Alison is arrested for driving under the influence. She turns to Billy for comfort when Zack neglects her, but Billy reaffirms his relationship with Susan. Alison is cleared of all charges because witnesses felt that the bicyclist had been at fault. Bruce fires Amanda when he realizes that she leaked information and scuttled a possible merger. Kimberly takes Jo to the beach house and induces labor. She checks Jo into the hospital, claiming that she delivered a stillborn child. When Jo shows up at the beach house to take the baby, Kimberly insists that the boy is her child. After Jane allows Chris to deposit a $500,000 check, Chris clears out Jane's account and kidnaps Sydney.

Bruce learns that D&D has been purchased by a consortium of doctors. Peter fires Bruce and appoints Amanda president. Amanda gives Billy a promotion and orders him to fire Alison, who has begun to experience blackouts. Bruce hangs himself in Amanda's office. Matt tells Billy that he can save Alison's job by checking her into rehab. They conduct an intervention, and Alison agrees to seek treatment. She escapes when the trio stops for gas, but later checks herself into the clinic. Sydney decides that she doesn't mind being a hostage when Chris buys her expensive gifts and gives her unlimited use of his credit cards. She finally calls Jake and asks for help after Chris loses all of Jane's money and becomes abusive. Michael, Jane and Jake fly to Las Vegas, where Jake expresses his doubts about Sydney's behavior. Jane and Michael learn that all the money is gone, and sleep together. Michael demands to know why Kimberly suddenly has a child. Jo struggles to prove that her son is alive.

Alison clashes with a man in her group meeting, NFL quarterback Terry Parsons. When Billy fails to show for a meeting featuring loved ones, Alison sneaks out to a bar and gets hammered. Terry helps her get sober and explains his earlier behavior. Billy is outraged when he learns that Susan failed to tell him about Alison's meeting. He lights into her, prompting Susan to move out. Peter displays increasingly controlling behavior toward Amanda. Jane sends a note and flowers from Michael back to the beach house, and Kimberly threatens to divorce him. The baby becomes very ill and is raced to the hospital. Michael refuses to return the child to Jo, even after a blood test proves she is the mother. Jeffrey is livid when Matt reveals his HIV positive status to the neighbors (to explain Jeffrey's panic over a bleeding cut). Jake breaks up with Sydney after learning that she slept with Chris.