Alison's roommate leaves in the middle of the night and sticks her with the rent. The goofy Billy Campbell approaches her and asks about the vacancy, but she turns him down. Faced with eviction, she finally takes him up on his offer. Alison accidentally dents the car door of a vice president at the ad agency that employs her, D&D. She accepts a date with him, but Billy has to come to the rescue when the man tries to force his way into the apartment. Jake attempts a relationship with Kelly Taylor, a teenager whose house he had helped remodel. They are constantly faced with obstacles due to their age difference. Rhonda is pursued by one of her aerobics students, but learns that his interest is anything but romantic.

Billy is depressed when the Melrose Times folds. He asks Alison to accompany him on a visit to his parents' house, then pleads with her to pose as his girlfriend. Billy tries to convince his parents that he is on the verge of becoming a successful writer, but is roped into helping run his father's furniture store because of a deal the two once made. He quits in a huff after his father questions his sales techniques, and later asks his dad to let him live his own life. Sandy gets a swelled head after landing a part in a horror movie, and ends up moving out. She comes down to earth after the director tries to insert nudity into one of her scenes. Michael injures himself at the apartment. He and Jane discuss their excitement and anxiety about the upcoming birth of their baby.

Alison undergoes successful surgery, and Billy agrees to care for her when she returns home from the hospital. They both become frightened by how much they have come to care about each other. Jake and Jo observe that the necklace Billy plans to give Alison for Christmas is more than a ""friendship"" present. Billy disagrees, but decides not to give Alison the gift after she makes him agree to a ""no presents"" pact (because she is short on cash). Alison fears that she has hurt Billy's feelings. She later apologizes, and he gives her the necklace. They admit that they have become confused by their feelings. Jo and Jake try to overcome their unhappy memories of Christmas. He is excited about making a fresh start, but she remains cynical and wants to ignore the holiday. She also tries to push Jake away, but they end up having a hot make-out session. Michael is depressed when he and Kimberly cannot save a young gunshot victim, but his spirits are revived after delivering a baby for t

Alison is promoted to junior account executive and works with art director Amanda Woodward on an underwear account. Alison flirts with the handsome tennis star who is modeling for the account. She decides not to pursue him because she fears it could affect her career. Jo is hired as photographer, but jeopardizes the account with her ""alternative"" photos. Alison gets into hot water when she takes a risk and shows the client Jo's photos, even though they had already expressed approval about the more traditional shots. Jo upsets Jake and Alison by going to dinner with Rex. She later apologizes to Jake and admits that she has strong feelings for him. Billy doesn't hit it off with a blind date arranged by Michael, but is attracted to Amanda. An overwhelmed Rhonda breaks her engagement after Terrence tries to buy them a house in the suburbs.

Jake and Jo are forced to submit to AIDS tests after his ex-girlfriend Peri reveals that she is HIV positive. Unable to cope with their anxiety, Jake and Jo take off on his bike and spend the night in the desert. He apologizes for the situation, and they confess their love. They declare that they will appreciate their lives more, regardless of the test results. Their tests come back negative, and Jake offers his support to Peri. Billy uses an embellished résumé to win a job at Escapade Magazine. His boss, Nancy, develops a crush on him. Alison returns to D&D and begs for her old job. Unfortunately, Amanda is in charge of hiring for the position. She lets Alison work as a receptionist, until Lucy forces her to re-hire Alison. Amanda continues to treat Alison badly, but denies that it has anything to do with Billy.

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

The apartment building goes up for sale. Lucy resigns from D&D, and tells Amanda and Alison that promotions may be in their future. Amanda asks Alison to keep her pregnancy under wraps, but Alison lets it slip while out drinking with a colleague to make Billy jealous. Amanda denies the man's allegations. She later suffers a miscarriage while working late with Alison. Billy and Amanda grow closer as he consoles her, and he is torn between the two women. An unidentified individual begins harassing Alison. Keith returns to Los Angeles, completely obsessed with Alison. Michael and Jane rekindle their romance during a weekend getaway. Jo tries to dodge Jake's discussions of commitment. She is arrested for carrying a concealed weapon while working on a photo essay about the homeless. Jake is enraged to learn that she went back on her promise to get rid of the gun. Rhonda proposes to Terrence. Keith stakes out Alison's apartment, and attacks Billy from behind with a tire iron. While Billy is

Billy shows up at Keith's work site and assaults him. After Alison tells Keith that she hates him, he commits suicide while on the phone with her. Alison begins drinking and is sent home from work. Amanda tries to convince Jake to model for a beer campaign. Sydney caters to Michael's every whim, despite a warning from Jane. Matt is hired by the hospital's social services department.

Sydney gets a waitress job at Shooters. Kimberly catches Michael in bed with Sydney. She tells Jane, who rejects Sydney. Kimberly moves out when Michael refuses to leave the beach house. A drunken Michael interrupts Jane's dinner with Robert's parents. Matt gets a date, but is distracted when Katya and an ailing Nikki have to move into his apartment to fool an immigration official. Alison is jealous of Steve's relationship with Jo.

Alison complains to the brass about Amanda's mistreatment of her. After the FBI shows up with questions about her father's disappearance, Amanda is ordered to take a vacation. She heads to Hawaii with Jake, but returns because she fears that Alison is after her job. She goes to Billy and threatens to expose their one-night stand unless he gets Alison to back off. He refuses to cave in, although Alison ends up apologizing to Amanda anyway. Sydney sets up a hooker with an unknowing Robert during a business trip. Jane receives a videotape of the two together and breaks up with Robert. Reed and Jo sleep together. He later decides to start a charter boat service.

Sydney and Jane get into a catfight in the pool after Syd tries to take Jane's wedding dress (a family heirloom). Their mother comes to town, but cannot talk Syd out of the marriage. Michael and Sydney are married at the beach house, with only Matt in attendance. Inspired by a dream, Michael decides to take Syd on a honeymoon and murder her. Jo learns that she is pregnant with Reed's child, and plans to have an abortion. Jake takes her to dinner instead of dining with Amanda and her boss. Amanda is jealous of the amount of time Jake is spending with Jo, until she learns about the pregnancy. Jo decides to have the baby. Billy's co-worker Celia and Alison (inspired by a comment from Amanda) lay a guilt trip on him until he buys Alison a more expensive engagement ring.

Jo is certain that Amanda will not gracefully bow out of her relationship with Jake. Hillary refuses to believe that Chas tried to seduce Amanda. Chas files a $10 million sexual harassment suit against Amanda, and the agency does not support her. She turns to Jake for consolation. Sydney is assaulted by three hookers when she invades their turf. Kimberly comforts her and pays her rent. She convinces Syd to participate in her plot to kill Michael, and they plan the crime over ice cream. Michael stands in the way of Jane's plans to expand her business. Billy's college friend Rob comes to town to serve as his best man, and gets along well with Matt. Billy is stunned to see them kissing in the courtyard.

Jake sleeps with Amanda. Jo catches him coming out of her apartment half-dressed. Jake insists that he doesn't want to reunite with Amanda, but Jo breaks up with him. Amanda tries to make nice with Alison in the hopes of convincing her to not to testify on Chas's behalf. Kimberly drugs Michael, and she and Syd leave him in his car with the engine running. However, Jane revives him when she and client Chris Marchette come over to discuss a business deal. Before the wedding, Michael refuses to sign off on Jane's business proposal, so she threatens to kill him. Kimberly steals Jane's car keys. As Alison is about to walk down the aisle, her father's words of reassurance trigger a repressed memory. She realizes that her father molested her during her childhood. He threatens to kill her if she tells anyone. Alison fails to emerge for the ceremony, and Jane and Billy discover that she has fled through the window. She seeks refuge at her sister Meredith's San Francisco home, unaware that her f

Chris warns that his company will have to cancel his deal with Jane's firm if Michael does not sign off on it. Sydney calls Matt from the mental hospital and pleads with him to investigate Kimberly. Jane and Matt visit the beach house, where she bonds with Michael while Matt snoops. He discovers that Kimberly owns several wigs, then rips off her wig during a confrontation at the hospital. Sydney accepts a plea bargain after a scummy staff member propositions her, and is released into Jane's custody. Kimberly vows revenge against Matt. Palmer and Brittany continue their plot against Jake. Palmer turns up on Amanda's doorstep. Billy and Alison break up after she learns that he took a job at D&D without consulting her. Jo receives a surprise visit from Reed's parents. She reluctantly admits that Reed is the father of her child, and is shocked when the Carters sue her for custody.