After Michael shuns her, Sydney tells Jane the truth about her involvement with prostitution and Michael's scheme against Robert. Jane blames herself for Sydney's problems, and throws Michael out. Sydney is acquitted because of an incompetent prosecution team. Jo is angry when Reed approaches Amanda as a potential investor in his charter boat service. Jake confronts Reed about his intentions toward the two women in his life. Billy wins a promotion, but learns that the job requires a move to New York. Matt is annoyed by the bizarre behavior of his new love interest. He learns that the man is a closeted Navy officer.

Amanda and Jo invest in Reed's business, and Jake is hired as chief mechanic. Jo displays a lack of trust toward Reed after he leaves a suitcase of personal possessions in her care. Michael becomes addicted to painkillers. Jane files a restraining order against him. She calls the police when Michael shows up at her apartment, but Sydney gives him refuge. After Michael talks Syd into getting him more pills, she finds him passed out on his bathroom floor. Alison refuses to move to New York with Billy, and suggests they try a long-distance relationship. Jeffrey fears that his relationship with Matt could jeopardize his career.

Jake and Amanda pull out of Reed's business when Jake discovers some inconsistencies in his story, but Jo accuses him of jealousy. Reed picks up a shipment of drugs on the boat while Jo is sleeping on board. When Jo discovers drugs stored in a compartment below deck, Reed assaults and kidnaps her. Sydney overhears a semi-comatose Michael babbling about his plea for Matt to change his blood alcohol results. She lays the groundwork for a blackmail scheme. Frustrated by her inability to get in touch with Billy, Alison flies to New York to surprise him. She is stunned to find him having drinks with another woman. Jeffrey is transferred to the east coast after coming out of the closet.

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 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.

Amanda is forced to confront her Scrooge-like behavior when Bruce appears to her in a dream and leads her in a version of The Christmas Carol. He encourages her to break free of the hold that Peter has over her. She visits Alison at the rehab center to apologize, and ensures that Bruce's children are financially secure. Terry becomes jealous after seeing Billy and Alison together, and admits his own feelings for her. Matt and Jo tell Peter that Kimberly has stolen her baby. Peter orders Michael to return the child to Jo. Kimberly goes ballistic and tries to throw herself in the ocean. After Michael saves her, she calls Mrs. Carter to tell her that her grandson is alive. Jeffrey breaks up with Matt because he needs time alone to cope with his illness. Jane convinces Syd to come home for the holidays.