Season 5, Episode 13 – Aired: 12/16/1996
Crazy Love

Sydney resents Jane's new relationship with her mother. Sherry lies about the identity of Jane's biological father, but later reveals that he was a producer with whom she had slept to win a part. Amanda and Craig take a business trip to Palm Springs. When Peter arrives to surprise Amanda, he finds her having dinner with Craig and wearing a pearl necklace. Peter refuses to listen to her explanation, and trashes the restaurant. Amanda throws him out of the apartment. Taylor decides to donate one of Samantha's paintings to a charity auction. Sam (who hasn't received any money from the sales) tries to buy it back, but Sydney bids on the painting to drive up the price and make Kyle look generous. Sydney is in a bind when she accidentally buys the painting, and hopes that the man who bid against her will take it off her hands. He is actually an employee of computer genius Carter Gallavan, who buys the painting and takes a liking to Syd. Billy retrieves the painting that Sam gave to Craig. Billy and Sam decide they belong together. Kimberly plans to die in a staged accident so that Michael can benefit from her insurance money. Jake and Alison take a Christmas getaway to Park City. Dan showers Matt with gifts in an attempt to gain control of him.

Season 5, Episode 15 – Aired: 1/13/1997
Escape From L.A.

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.

Season 5, Episode 17 – Aired: 1/27/1997
Better Homes and Condos

Kimberly pulls Michael from the wrecked vehicle while Megan calls for help. Michael experiences internal bleeding, and flatlines. He dreams that Kimberly is a devil trying to lure him into the Melrose pool, while Megan is an angel who wishes to rescue him. Peter revives Michael, who credits Megan with giving him the strength to go on. Megan convinces Michael to support Kimberly in her final days. Sydney stakes a claim on Jane's old apartment, forcing Samantha to the streets. Sam seeks the legal assistance of her attorney ex-boyfriend, Kenny. Billy is about to ask Sam to move in with him when Kenny arrives and threatens to sue Amanda. Amanda declares that Sam can stay as Sydney's roommate. Syd spends a romantic weekend with Carter in San Francisco, but it is cut short when Carter discovers how to repair a glitch in one of his computer games. Walter convinces Carter that Syd is extorting money from him. Peter moves into a new house, but seeks to maintain a relationship with Amanda. Taylor is annoyed when Kyle's boorish marine buddy, Nick, comes to town and moves into their apartment. Jake finds his dream house, but Alison is unsure about moving.

Season 5, Episode 19 – Aired: 2/3/1997
Great Sex-pectations (2)

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 Amanda. A drunken Jake stands in the courtyard screaming at her. Sydney forces Carter to realize the truth about Walter. Carter quits his company and moves in with Sydney.

Season 5, Episode 21 – Aired: 2/17/1997
Men Are From Melrose

Nick follows Taylor to Peter's house and witnesses a romantic encounter. He later photographs the couple's late-night rendezvous at a golf course. Megan discovers that Kimberly's illness is in remission. Michael reaffirms his decision to stay with Megan; but she is disturbed by a visit from Josh, her former pimp. David tells Jake that he knows that he is his father. Billy disapproves of Sam's attempt to reunite Alison and Jake. Billy later apologizes to Sam, and Alison takes Jake back. Sydney and Carter are robbed at knifepoint, but Kyle punches the man out and chases him away. Carter asks Sydney to join him on a getaway in Mexico, but overhears her telling a boutique customer that she loves Kyle. When Syd arrives at the airport, Carter tells her that he is returning to his company, and wishes her a nice life.

Season 5, Episode 23 – Aired: 3/3/1997
Screams From a Marriage

Amanda rejects Craig, who seeks a relationship after their night together. Kyle realizes that Taylor has been lying to him. He visits Nick's motel room and forces him to play the recording. Nick threatens to kill Peter unless Taylor pays him $5000. Nick attacks Peter with brass knuckles. Kyle stops Nick from killing Peter, and helps him skip town. Kyle throws Taylor out of the apartment. Josh plays Megan and Kimberly against each other. Megan is arrested for soliciting an undercover cop. Michael bails her out, but breaks up with her. Matt's brother Luke dies in a plane crash. Matt is shocked to learn that Luke named him the guardian of his teenage daughter, Chelsea.

Season 5, Episode 25 – Aired: 3/17/1997
From Here to Maternity

Kimberly collapses during an argument with Michael. She learns that she has an aneurysm, but refuses to undergo surgery. Megan (who has been hired as Burns/Mancini's receptionist) tries to use company money to pay for a private nurse. Michael accuses Kimberly of faking her illness, and arrives at the beach house to find her clinging to life. He calls her mother and suggests that she come to L.A. Matt is unable to track down Chelsea, but she later checks into a halfway house. Samantha convinces Chelsea to return home by sharing her own experiences as a runaway. Matt agrees to let Chelsea stay with him, although his mother doesn't feel that he is a fit parent because he is gay. Sam comes home from a date with Billy to find her father, who says he has been released from prison. Sydney meets Hilda's sleazy lawyer, Harry Dean, and begins to suspect that Hilda is faking her injuries. Jake is angry when Alison disobeys her doctor's orders by going back to work for a presentation. She later collapses in pain. Amanda tells Craig that she is taking a vow of celibacy.

Season 5, Episode 27 – Aired: 4/7/1997
The Dead Wives Club

Jake and Alison hit the road in the hopes of finding a place to get married. Their car breaks down in a small town, where they eventually tie the knot. Jake allows Alison to sample some of the champagne provided by the motel manager. Sydney rejects Harry's overtures and returns to work at Kyle's. Kyle refuses to get involved with Syd because he is not ready for a relationship. When Sydney sees Amanda making time with Kyle, she decides to participate in one of Harry's scams to take her down. Syd hurls herself down the stairs at D&D while waitressing at a party. Taylor realizes that Peter is trying to turn her into Beth, but decides to go along with it to make him happy. Kimberly appears to Megan in a dream and warns her that Michael destroys his wives. Megan backs out of Michael's scam to discredit Peter. Chelsea's mother, Denise, apologizes for leaving her; she convinces Chelsea to live with her in Europe. Reilly threatens Billy. Samantha learns that her father escaped from prison, but won't turn him in.
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Season 5, Episode 29 – Aired: 4/21/1997
All Beths Are Off

While having lunch with Megan, Jennifer hears Kyle's voice. She slaps him. Kyle visits her at the beach house, and apologizes for the way he broke off their Boston affair. Michael throws Jennifer out after learning about the affair, and that she has dropped out of school. Amanda and Kyle find the space for their jazz club, but Amanda isn't sure she should get involved with him after hearing of his flings with Syd and Jennifer. Sam's father refuses to leave town, and extorts more money from her. Denise convinces Chelsea to keep a diary as evidence against Matt. She takes notes when a male friend who has just lost his lover to AIDS spends the night on Matt's couch. Craig and Sydney draw closer. He chases away a private investigator hired by Amanda to spy on Syd. Billy is alarmed to learn that Alison is drinking, but Jake isn't concerned. Alison gets fired after drinking and causing D&D to lose a client. She and Jake decide to adopt. Michael pledges to help Taylor after learning of Peter's bizarre behavior.