Alison and Hayley honeymoon at a luxurious hotel/resort in Cancun, which he owns. Alison overhears Hayley arguing with the hotel manager over finances. She is further distressed when Hayley tells Brooke that he and Alison will not have children. Amanda pushes Peter away. Jack's father orders his other son, Bobby, to ""take care of"" Amanda. Michael is pleased when Sydney throws him a surprise birthday party, but threatens to cut her loose when he learns she is blackmailing Peter. Jane decks Jo after she overhears her making a catty remark to Richard. Jane decides to begin dating Michael to make Richard jealous. A lonely Kimberly has a fling with the pool boy. Matt and Jake discover that bookkeeper Shelly hasn't given Jake the password to Shooters' computer records. Meanwhile, Shelly fills a safe deposit box with cash.

Kimberly's bed-hopping puts her life in danger when her latest conquest turns out to be Vic, a psychotic man who has made threatening calls to her radio show. He ties her up and holds her hostage in a condemned building. Shelly tries to cover her tracks, but Jake eventually learns that she has been embezzling from Shooters. She tries to stab Jake when he confronts her. Peter convinces Amanda to open up to him. She tells him that she loved a man before she met Jack, and was deeply hurt when he left her. Bobby follows Amanda for a few days before finally coming to her apartment. She is angry at first, but then embraces him. Jane creates problems between Richard and Jo after she begins dating Michael. Hayley suddenly decides to sell his house. He wakes Alison in the middle of the night and says they are taking a second honeymoon. Billy and Brooke move into Alison's old apartment.

Hayley takes Alison away on a cruise. He reveals that he has serious financial problems, and throws his records into the ocean. Hayley plans to flee to Mexico, and Alison agrees to join him. A drunken Hayley falls overboard in the middle of the night. The Coast Guard later recovers his body. Kimberly manages to knock Vic unconscious and free herself. She hauls Vic into the police station. Kimberly tells Peter that she is giving up her radio career to become a psychiatrist. Amanda suspects that Bobby is going to kill her, but he says he came to Los Angeles to protect her from his family. Peter is furious when Amanda has dinner with Bobby, especially after he learns Bobby is the ""first love"" Amanda had described to him. Syd confronts Jane about her intentions toward Michael. Jake is frustrated by the police investigation of Shelly. He finds that most of his money is already gone.

Brooke blames Alison for Hayley's death, and arranges for Alison to be taken in for questioning. The death is ruled an accident. The bulk of Hayley's estate is left to Brooke's unborn child. Hayley left nothing to Alison, as he had actually secretly divorced her a week before his death. Brooke quits her job. Alison insists on making a presentation at a software convention, but fails to show for a lunch meeting. Billy drives to the hotel and finds that Alison has been drinking. Bobby seeks Peter's help in rehabilitating his family's image. Amanda sees Bobby in a new light after the FBI harasses him. Sydney reluctantly turns to Kimberly for counseling about Jane's involvement with Michael. She suggests Syd push the two together to get it out of Michael's system, but the plan backfires. Jake turns to a loan shark friend to cope with Shooters' crisis. Matt befriends Alan Ross, an actor who was treated for a broken arm.

Billy makes the presentation in Alison's place. When Brooke arrives, Billy claims that he slept with Alison (in order to prevent Brooke from finding out that she is off the wagon). Brooke learns that she is not really pregnant, but doesn't share the truth with Billy. Kimberly suggests that Sydney organize the hospital Christmas party to boost Michael's career. Bobby agrees to host the event. When Jane monopolizes Michael's time, Sydney slips tranquilizers into her drink. Jane and Michael head upstairs. As Michael is called to the podium to give the keynote address, he runs out of a bedroom in his underwear and says that Jane collapsed. Richard and Jo plan to force Jane from the business, but Jo has a change of heart when Jane extends an olive branch. Matt and Alan get closer.

Jane has suffered a stroke, and is left paralyzed on one side. Sydney insists that she did not realize the pills would cause this reaction. Kimberly suggests that Syd dodge suspicion by becoming Jane's caretaker. Jane moves into the beach house. Brooke asks Billy to meet her at the hospital, and says that she has suffered a miscarriage. She pushes Billy to get her pregnant ""again,"" as she can only gain access to Hayley's money through a child. Billy learns the truth from Brooke's doctor, and declares that the marriage is over. Bobby convinces Amanda, Peter and Alison to join him for a weekend in Palm Springs. Billy drives down to talk with Alison, who decides to leave early. Bobby declares his love for Amanda. They kiss at midnight on New Year's Eve, as Peter secretly looks on. Bobby settles a malpractice suit for Peter. Matt stops Alan from moving to New York by asking him to move in with him. Billy arrives home to discover that Brooke has slashed her wrists.

Brooke survives her suicide attempt. A guilt-ridden Billy returns to her side and demands that Amanda rehire her. Peter gives Bobby an ultimatum. Bobby stops by Amanda's apartment to tell her that he is bowing out, but she sleeps with him. Kimberly suggests that Sydney incriminate someone else in Jane's accident. She slips some pills into Richard's desk, where Jo finds them. Jo turns to Jake for advice, but he has nothing to say to her. Michael moves out after Sydney accosts him for trying to take advantage of Jane. Monty asks Jake to collect from another of his ""customers"" to pay off his interest, but Jake cannot go through with it. Alan shies away from Matt after Kimberly shares the sordid details of his past relationships.

Alison tries to show some sensitivity toward Brooke, who responds by trashing Alison's apartment. When Billy confronts Brooke, she goes ballistic and throws dishes and pasta across the room. A fed-up Billy walks out on her. Amanda breaks up with Peter to pursue a relationship with Bobby. Peter flirts with Bobby's lawyer, Alycia (who defended Matt against the murder charge). Alycia tells Jake that her (unidentified) client has bought his loan from Monty. Michael agrees to come home from Peter's if Sydney can get Jane out of the beach house. Syd tries to dump her off at a cheap convalescent home, but Jane refuses to go. Sydney leaves Jane on the beach while she has dinner with Michael. Jake saves Jane from drowning. Jo believes Richard's claims of innocence regarding the pills. Alan wins a role on a soap opera.

Vince is furious when he learns that Bobby did not kill Amanda. He shows up at their hotel during a weekend getaway and holds them at gunpoint. Billy files for divorce. Michael injects Kimberly with truth serum and gets her to admit that Sydney drugged Jane. She also tells Michael that she loves him. Michael throws Sydney out, and Kimberly asks her to stay at her apartment. Peter begins dating Alycia. Jane regains the use of her legs. She announces that she is quitting Hart-Mancini to concentrate on her own work. Matt is wary when Alan gains an on-screen reputation as a ladies' man.

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

Alison and Billy pull Brooke from the pool, but she is already dead. Billy is haunted by nightmares about Brooke. Michael goes to great lengths to convince Kimberly to move back in with him. Alycia threatens to quit when Bobby warns her to stay away from Peter. She catches Peter going through her files. Jane and Richard resort to underhanded tactics as they fight over a potential client. Matt is wary of Alan's relationship with his leading lady, until he learns she is a lesbian. She warns that the show's producer destroyed her relationship, and could do the same to Matt and Alan.

Kimberly is hurt when she receives divorce papers, although they had been filed months before her reconciliation with Michael. He suggests that they have a real wedding at the beach house and renew their vows. Michael fires Sydney at Kimberly's request. Sydney sues Michael and Peter for sexual harassment, and they are forced to appoint her office manager. Peter stifles Alycia's suspicions by claiming that his father was destroyed by the Parezis. They launch a plan to ruin Bobby's image by making it appear that he is bribing a senator. Jo accidentally takes Jane's sketch pad, and the designs are included in Richard's new line. Alison is outraged when Billy embarrasses her in front of a client to set up his own pitch. They later sleep together, and Billy tries to bully Alison into moving in with him. Alan tells Matt that the show's producer has decided that he and his co-star, Valerie, should marry as a publicity stunt.

Alison is put off by Billy's obnoxious behavior, and pushes him away. Amanda agrees to give Billy a raise if he can win a prestigious airline account. He sleeps with a rival executive to get her to reveal their strategy, then uses it to undermine them. Amanda turns to Peter for comfort after the bribery allegations against Bobby become public. An incensed Alycia threatens to reveal Peter's scam unless he stays away from Amanda. Jane has to cancel her fashion show because Richard has taken her designs. She sabotages Richard's show by using a tiki torch (part of the show's theme) to trigger the sprinkler system. Kimberly begins suffering migraines.

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.

Bobby is arrested for assaulting Peter, but Sydney later convinces Amanda to have the charges dropped. Peter makes a deal with Billy's client so that he can pay off Alycia and escape her influence. Alycia takes over Bobby's company. ""Betsy"" throws the couch off the deck and sets it on fire, and later tries to maim Michael. Jake is furious to learn that Jane sabotaged Richard's show. He gets drunk during a fashion convention and sleeps with a stranger. The woman is later hired as Jane's new assistant. Alan outs himself to a tabloid because he can no longer live a lie. Matt is hesitant to take him back.

Billy uses underhanded means to steal the keynote speech at an ad convention away from Alison. He makes an emotional speech about lying, and reveals that he has sold his soul to become a star in the industry. After Billy is a hit at the convention, Amanda sleeps with him. Alison quits her job and learns that Amanda is using Billy to help her career. Kimberly develops another personality, a cool biker chick named Rita. She refuses Peter's medical advice. Sydney blackmails Alycia into rehiring Bobby, but he instead seeks honest work as a mechanic. Sydney offers to let the homeless Bobby stay at her apartment. Claire has been hired by Richard to break up Jake and Jane. She tells Jane that she is having an affair with Jake. Jane fires Claire and breaks up with Jake. Jake rejects a reconciliation attempt by Jo and crawls back to Jane.

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.

Teri threatens to expose Michael's actions to Kimberly unless he lets Peter take the fall for sleeping with Brandi. Amanda apologizes for doubting Peter. He refuses to meet Teri's settlement demands. Kimberly begs Peter for help with her illness. Before he can treat her, he is arrested for statutory rape. Amanda learns that Michael was the one who slept with Brandi. Kimberly argues with ""Betsy,"" who conks Michael on the head with a hammer. Matt asks one of his medical school professors, pediatrician Dr. Dominick O'Malley, to look at Tyler. He finds no evidence of abuse. Laurie tells Jo to mind her own business. Billy's string of success with ad campaigns comes to an end. He decides that he must put his obsession with Brooke behind him and move on. Richard rapes Jane during a business trip to New York. She pushes Jake away and doesn't tell anyone what has happened. Sydney inadvertently becomes a porno producer when she invests money with an old acquaintance of Bobby's.

Amanda persuades Teri to drop the charges against Peter by making Brandi the spokesperson for a cosmetics company. ""Betsy"" throws a knife at Michael after he reveals that he slept with Brandi. When he returns, Kimberly begs him to stay away for his own good. She turns to Peter for help, but vanishes before he can aid her. Bobby's friend Jimmy tells Sydney that Alycia and Peter conspired to take Bobby down. Syd shares this news with Bobby, who sets up a confrontation with Alycia. When he tries to attack her, she knocks him out a high-rise building to his death. As Peter is about to be questioned about Bobby's death, Alycia calls from her car and confesses. She agrees to turn herself in, but loses control of the car while picking up her phone, and has a head-on collision with a semi. Dominick gets Matt to set him up on a date with Jo. She convinces him to see Tyler again, and Laurie reveals that the boy was abused by her ex-boyfriend. Jane tells Jake about the rape in the hopes that he w