Alison remains irritated about Billy's relationship with Amanda. Amanda suggests that Alison might have feelings for Billy, and recommends that the two discuss their relationship. Alison begins to consider this possibility, and Billy agrees to meet with her. Someone sends flowers to Alison at work and asks her to meet him at Shooters that night. She assumes that the flowers are from Billy (creating problems for Billy and Amanda), but is instead approached by a newly divorced Keith. She agrees to give their relationship another try, so long as they take things slowly. Alison and Keith have a disastrous dinner with Billy and Amanda. Billy goes home with Amanda and sleeps with her. Jo's husband offers her a $50,000 divorce settlement, but she wants to turn it down because of her pride. Jake feels that this is a foolish decision from someone who doesn't know what it's like to be poor. Jake loses his job when the repair shop goes out of business. He believes that he could take ov

Billy and Alison's first real date is a disaster, as she is fretting about Michael's affair and he has only one thing on his mind. Before they can try again, Alison is called away to a work retreat in Palm Springs. Michael has Kimberly beep him during his anniversary dinner with Jane because he decides he would rather sleep with Kimberly. On her way out, Alison tells Jane about Michael and Kimberly, but she doesn't believe her. Michael denies everything and tries to plant doubts about Alison, but Jane later catches him at Kimberly's apartment. Alison and Amanda come to a truce after Amanda shares her feelings about Alison's interference in her relationship with Billy. Jake loans Billy a motorcycle so that he can surprise Alison in Palm Springs. Amanda mistakenly receives a note from Billy intended for Alison. She tries to send him away, claiming that Alison is on probation at work and cannot see visitors for fear of losing her job. Alison goes to the parking lot to retrieve som

Michael convinces Kimberly to have dinner with him. When she rejects his marriage proposal, he becomes very drunk. Kimberly changes her mind during the drive home, but Michael loses control of the car during their celebratory kiss. The car flips off an embankment, leaving Michael paralyzed and Kimberly in a coma. Michael blames Syd for the accident. The police suspect that Michael was driving under the influence. He pleads with Matt to change the results of his blood alcohol test. One of Sydney's co-workers takes her to a party. She makes a date with a director, unaware that he is under the impression that she is a hooker. Jo gives Alison the cold shoulder, and warns her that she is on the verge of destroying her relationship with Billy.

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.

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.

Amanda and Michael clash over the treatment of her cancer, but she eventually realizes she must turn to him for support. Amanda shares her condition with Billy, but asks him to keep it a secret. Alison pries the truth from him after he seems a little too tolerant of Amanda's behavior. Sydney attends a retreat with Rikki and other cult members. She finds it unsettling when Martin demands that his followers try to scam money from their families, and decides to leave after seeing Martin in bed with two women (including Rikki). Martin agrees to let her go, but he and Rikki pursue her and throw her into an underground pit. John pulls Kimberly out of her car and threatens her at gunpoint after learning that she orchestrated the attack on Matt.

Martin lets Sydney out of the pit and talks her into staying. Jane and Jake drive to Tucson to rescue Syd, but she refuses to leave with them. They return the following day, and Sydney is alarmed when Martin asks her to shoot her sister. She instead shoots up the camp and flees with Jake and Jane. Kimberly is furious to learn the role Michael is taking in Amanda's treatment. Matt nixes a relationship with John. Jo goes on a ride-along with John to get photos for an underground magazine, and secretly snaps pictures of John beating a drug dealer. She claims she didn't see anything, but John trashes her apartment. Billy and Alison spend a platonic Valentine's Day together.

Alison goes to the Century Awards headquarters to submit Amanda's entry. An employee named Brooke Armstrong convinces Alison to also enter her own campaign. Alison and Billy get carried away while working late in his apartment. Kimberly catches Amanda and Michael in a hot tub together during a weekend retreat in Santa Barbara. Michael claims that he has decided to ignore Amanda's "obsession" with him, but later escorts her to the awards dinner. Amanda is outraged when Alison wins the award for best print ad. Michael professes his love to Amanda. Sydney's antics break up a romantic dinner between Jake and Jane. Jake dumps Jane after she issues an ultimatum about avoiding Sydney.

Alison replaces Amanda as D&D president. Alison has a liaison with Billy in her new office, but quickly rejects him. Brooke gets an internship at D&D. Michael tries to scam the city out of a million dollars by claiming that poor road conditions caused his and Kimberly's accident. Michael ships Kimberly to Rochester for a job interview so that he can move Amanda into the beach house and watch over her. Amanda collapses and is hospitalized in serious condition. Jake learns that his mother has died. He and Jo drive to Ellensburg, Washington for the funeral. They encounter Jake's half-brother Jess, who is feeling guilty over his mother's death. He also harbors resentment toward Jake. The poverty-stricken brothers once robbed a store, but Jess took the heat. He feels that Jake abandoned him by leaving for California. Jake and Jo sleep together again, but still decide not to get back together. Jake establishes a truce with Jess.

Jake throws Jess out of his apartment, and assaults him after his brother taunts him about Jo. Jess hires a thug to stage a robbery at Shooters and shoot Jake. Brooke convinces her father, Hayley, to offer Alison a job in Hong Kong. Billy follows Brooke's advice and persuades Alison to take the job. Alison writes a note to Billy in which she professes her love, but Brooke refuses to give it to him. Matt learns that Paul is married, but continues the relationship when Paul says that he needs Matt's help to come out. Paul's wife, Carol, threatens Matt's life. One of the alleged drug dealers reveals to Sydney that he is actually an FBI agent. He talks her into resigning so that she won't be implicated when the feds raid the design firm. Sydney is stunned to discover that the entire fiasco was a set-up engineered by Jane to oust her from the business. Kimberly seeks Amanda's friendship, then tricks her into believing that Michael is stalking her.

Jake suspects that Jess is responsible for his shooting, and is unmoved when Jess keeps Shooters open in his absence. Brooke replaces Alison's love note with a letter in which she states that long distance relationships cannot work. She also complicates Alison's efforts to get in touch with Billy. Billy proposes to Brooke along the boardwalk. Paul says that he is getting a divorce, and asks Matt to help him move out. He then stays inside the house and tells Carol that Matt is stalking him. Kimberly tries to convince everyone that Michael is stalking her, and makes Amanda believe that he vandalized her car. Kimberly trashes the beach house and scratches her own face. She calls the police, then stages a fight with Michael so that he will be arrested. When Kimberly returns to her motel room after a court hearing, a creepy man's image appears in a mirror and talks to her.

Brooke flies to Miami to investigate Amanda's past. She learns from an old newspaper article that Amanda was presumed dead years ago. She also visits the house of Amanda's ex-husband, Jack, claiming that her car has broken down. Brooke blackmails Amanda into giving her a promotion. Jack, who had swiped one of Brooke's business cards, arrives in Los Angeles. Billy learns that Alison has regained her sight. Michael pretends to have reconciled with Sydney in the hopes of driving Kimberly over the edge. Peter reveals to Syd that his concern for Kimberly stems from memories of a deceased sister who suffered a similar plight. Jane and Richard get engaged. Richard fires Jane after she publicly dishonors MacKenzie's memory, but is later forced to make her a partner. Jo is wary when Jake hires Shelly and allows her to stay at his apartment. Dr. Hobbs makes a homophobic remark about Matt to Michael. Michael encourages Matt to sue for wrongful dismissal.

Amanda gets into a scuffle with Jack as she struggles to escape. Jack trips over Amanda while pursuing her, and tumbles over the top of the staircase. Amanda calls Peter for help, as she fears the police would not believe her story. Peter claims that he stopped by the house and found that Jack had suffered an accident. Michael realizes that Peter's diagnosis is incorrect, but backs off after Amanda shares her history with Jack. Kimberly discovers that Mark Paul is a real person, and bullies him into admitting he was hired to scare her. Michael and Kimberly take their feud to national radio. Kimberly is furious when Peter neglects her in favor of Amanda. Alison agrees to move in with Hayley. Jake and Jo try to overcome their jealousy and stubbornness.

Amanda tells Vince that Jack was not the loving son that he remembers. Vince is outraged, but decides to let Amanda and Bobby go. He sells his shares in Bobby's cable company, leaving the business in jeopardy. Amanda agrees to help Bobby. Peter pays Syd to accompany him to a party and try to win Bobby away from Amanda. A financially strapped Brooke is thrown out of her hotel room. Alison convinces Billy not to have Amanda fire Brooke. Brooke tries to win back her ex-fiancé, but he laughs at her. Kimberly receives a call from Vic. When she visits him in prison, he vows that he will get out. Jane decides to start a business in Jake's garage. Jane's relationship with Jake is strained when she makes vicious comments to Jo. Matt accuses Alan of trying to keep their relationship under wraps.

Michael learns that Vic has been mistakenly released from prison. Vic hides in the back seat of Kimberly's car and kidnaps her at knifepoint. Michael steals a car and chases them. Kimberly's car crashes through a fence and into a semi. Michael pulls her to safety before the car explodes. Kimberly wants to just be Michael's friend, but later changes her mind during an especially friendly Scrabble game. Matt is furious when Alan conducts a TV interview in their apartment and says that they are ""roommates."" Alan apologizes and joins Matt at a dance-a-thon, but is livid when they are photographed together. Sydney warns Bobby that Peter is out to destroy his relationship with Amanda. Alison learns that Brooke is living in her car, and invites her to move in. Billy pushes her to end this arrangement. Brooke is fired for mouthing off to Amanda. A drunken Brooke shows up in the courtyard to confront Billy. After she is left alone, she stumbles, hits her head on the side of the pool, and sinks

Billy continues to irritate Alison with his win-at-all-costs attitude and boorish behavior. He befriends the chauvinistic president of a vodka company, and usurps one of Amanda's accounts. Alan's parents come to town for the ""wedding,"" and are unaware that their son is gay. They reveal that they have purchased a house for Alan and Valerie. A distraught Matt gets drunk and sleeps with his friend Dave. Matt walks out during the wedding, and Alan refuses to go after him. Jo discovers that Jane is responsible for the mishap at Richard's show. She blackmails her into hiring Richard as a consultant. Kimberly develops an alternate personality--a prudish, controlling woman named Betsy Jones. Amanda rejects Bobby, and he breaks down her apartment door. Peter is later knocked unconscious following a scuffle with Bobby.

Alison takes a job as a waitress at Shooters. Amanda uses Billy's status to her advantage in her contract negotiations. Kimberly asks Peter to take Michael out of town for a few days so that she can have time to herself. Michael and Peter head to Palm Springs, where they are judges in a teen beauty pageant. Teri Carson, the pushy mother of one of the contestants, tries to convince Peter to vote for her daughter. Her daughter, Brandi, seduces Michael. She does not win the pageant. Amanda dumps Billy to go back to Peter. She rejects Peter after Teri shows up on his doorstep and says that she is suing him for sleeping with her underage daughter. Sydney tries to bond with Bobby by getting him drunk and getting tattoos together. Sydney's friend Laurie comes to town with her young son Tyler. Jo takes them in because Sydney has no room for them. While babysitting, Jo discovers bruises on the boy's back. Matt laments the fact that Alan has moved to New York.

Jane and Sydney escape when Jane hits Richard in the gut with a shovel. As a deputy is driving Jane and Syd to meet Samantha, they see Richard come out of a grocery store. Richard is killed in a shootout. At the morgue, Jane stabs his body with a brooch to make sure that he is dead. A sheriff returns their money, and orders them out of his town. Jane stops a bewildered Sam from moving out. Sydney invests her money in Jane's boutique. Amanda threatens Kimberly when she refuses to perjure herself. Kimberly later ensures Peter's release when she recalls a waiter who can serve as his alibi. Amanda is angry when Taylor shows up at the courthouse. Billy mistakenly believes Alison has invited him to her apartment, and gets into a fist fight with Jake when he finds him there. One of Matt's professors suspects that he is on drugs.

Michael signs the divorce papers, and marries Megan during their trip to Las Vegas. Peter learns that Kimberly has a brain tumor, and breaks the news to Michael. Jane is robbed at gunpoint at the boutique. Sydney calls her parents, who come to Los Angeles to comfort Jane. Jane decides to go home to Chicago for a while, and agrees to stay in touch with Sherry. Sherry and Ed get engaged. Jane turns the boutique over to Syd, and says goodbye to her sister and friends at the airport. Alison learns that she is pregnant. Amanda gets Craig drunk during an evening out. He reveals that Arthur murdered Craig's grandfather when Craig was twelve. Matt agrees to move in with Dan. When Jake and Billy become suspicious of Matt's black eye, Dan accuses Matt of betraying him. He assaults him again. Sydney pushes Carter away when he still cannot find time for her. His assistant, Walter, tries to pay Syd to stay with Carter.

Megan becomes concerned by the amount of time Michael is spending with Kimberly. When Megan convinces Michael to ignore a call from Kimberly and spend the night with her, Kimberly suffers a seizure. Taylor discovers that the new chief-of-staff won the job because he is sleeping with Dr. Shulman. Peter uses this information to blackmail Dr. Shulman. Nick becomes suspicious of Taylor's relationship with Peter. Nick and Kyle are arrested in a barroom brawl at Shooters. Kyle offers to host Jake's bachelor party to make it up to him. Billy isn't sure that Jake and Alison are ready for marriage. Craig tries to use his expected inheritance to seduce Amanda. Roommates Syd and Samantha are at each other's throats. Billy asks Sam to move in with him. Carter continues to reject Sydney.

Kimberly persuades Michael to grant her dying wish by sleeping with her one last time. Amanda uses Craig's infatuation with her to trick him into giving her half of D&D. Craig learns that his father cut him out of the will. Peter is appointed chief-of-staff. Taylor offers to cook him a celebratory dinner, but he stands her up to go to a dinner party with Amanda. A drunken and depressed Craig shows up on Amanda's doorstep, and she lets him sleep on the couch. The next morning, Craig leads Peter to believe that he slept with Amanda. A distraught Peter sleeps with Taylor. Alison and Jake are to marry in a civil ceremony, but Alison hides in the bathroom at City Hall. Jake postpones the ceremony. Alison becomes fed up with Jake's attempts to control her and turn her into a housewife. She stays with Billy and Sam, then decides to visit her sister to avoid the meddling couple. Jake believes that Alison is going to have an abortion, but she does not. Alison returns home and moves in with Aman

Michael takes Megan back after learning that she has returned to the streets. A woman sues Sydney after she is injured by a display at the boutique. Kyle's plans to force Taylor from their partnership are squashed when Sydney accidentally tells Peter that she slept with Kyle. Alison is confined to bed due to complications in her pregnancy. She gets caught up on all the gossip as she overhears arguments in the courtyard. She hears Taylor tell Kyle that Peter was her brother-in-law. Although Jake feels Alison should mind her own business, he shares this detail with Amanda when she tries to blame herself for the failed marriage. Amanda has Craig drive her to Peter's house to confront the couple. She forces Peter to realize that Taylor's appearance in the apartment building was no coincidence. Matt finds it impossible to cope with Chelsea's rebellious behavior. She runs away after overhearing Matt agree to leave her with his mother.