During a routine appointment, Jane learns that her baby has died. Michael is reluctant to express his emotions about the loss, and quarrels with colleague Kimberly Shaw when she tries to convince him to show his feelings. He later apologizes, and the two flirt rather obviously. The Mancinis' friends give them a dog to help take their mind off of losing the baby, but Jane loses the dog at the beach. Michael lashes out at her and admits that he fears she may have lost the baby because she initially considered an abortion. He later apologizes for not being more supportive throughout the pregnancy. They find the dog, but let a lonely old woman keep it. Meanwhile, Alison is enraged after finding Billy fooling around with one of her bras while doing the laundry. She claims their friendship is over, but later explains the reason for her anger.

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

Jo faces murder charges following Reed's death. Jake is angry when Amanda refuses to help Jo because she could be implicated through her financial ties to Reed. She later has a change of heart, hiring her accomplished family attorney to represent Jo and putting up the apartment building as collateral for her bail. The charges are eventually dropped; the D.A. knew that Jo's crime was self-defense, but wanted to press her for information about Reed's associates. Alison accepts Billy's proposal. Billy tells Amanda that he wants to tell Alison about their one-night stand (but doesn't follow through), so Amanda confesses to Jake. At the engagement party, Jake decks Billy after being asked to serve as best man. Amanda explains the situation to Alison. Alison is stunned by the news, but forgives Billy. Sydney continues to charm everyone at the hospital, and even convinces the chief of staff to let Michael return to surgery. Despite his protests, Syd decides that she and Michael are getting m

Jake makes amends with Billy before leaving for a weekend fishing trip. Ted continues to creep around in the crawl space above Amanda's apartment. Jo realizes that someone is in Amanda's apartment; and she and Amanda catch Ted trying to escape. Amanda refuses to allow Jo to call the police until Amanda has tied up Ted and emotionally tortured him. Billy warns Dr. Miller not to interfere in his relationship with Alison. Alison ends their sessions, but not before Dr. Miller makes an astute observation about her relationships with men. Michael learns that Dr. Levin is a client of Sydney's business, and uses this information to blackmail his boss into appointing him chief resident. Michael tells Sydney that he wants to give their marriage a chance. As they kiss, Kimberly observes them from the beach below.

Kimberly threatens Sydney when she tries to stake her claim on Michael. Syd's business party is crashed by a newly freed Lauren, who breaks their earlier agreement and demands $15,000 by the end of the week. When Jane refuses to help her, Sydney takes a job as a stripper. Kimberly is still disturbed by Michael's marriage to Sydney, and makes plans for revenge. Alison is annoyed when Amanda hires her mother's fiancé, Chas. He refuses to take his share of the work, and ingratiates himself with Amanda by helping her smooth things over with Hillary. Alison later catches Amanda and Chas kissing in a conference room. Jo conducts a photo shoot with her model friend, Sarah, aboard the Pretty Lady. They are forced to stay for a few hours when the boat experiences engine trouble, and Jake and Jo nearly rekindle their romance. Sarah seeks refuge at Jo's apartment after her visiting boyfriend Hank attacks her. Hank shows up at Jo's doorstep and tries to come after Sarah. When Jo steps between them

Amanda is furious when Jake skips work to hold a bedside vigil for Jo. Jo is not seriously injured, and learns that her baby was unharmed. Billy warns Alison to keep quiet about Amanda's rendezvous with Chas. Jake tracks down Hank at a pool hall and beats him up. He shows up late for dinner with Amanda, sporting a black eye, and storms out when she lambastes him for defending Jo. Michael throws Billy a bachelor party at a strip club, unaware that Sydney is the entertainment. When she sees Michael, she runs out of the club and is fired. A drunken Billy accidentally tells Jake about Amanda and Chas. Jake breaks up with Amanda, who fires Chas and vows to destroy Alison. Jake admits his feelings for Jo, and she agrees to take him back. Kimberly alters the chart of one of Michael's patients, prompting him to unwittingly commit an error that nearly kills the man. He is stripped of the chief resident position. Kimberly bullies Jane into turning over the $5000 in profits she had kept from Mich

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.

Michael survives the hit-and-run, but suffers from amnesia. Jane is released when she offers evidence that incriminates Sydney. Kimberly promises to serve as Syd's alibi, then refuses to cover for her and plants a blonde wig at her apartment. Sydney is arrested. Billy deduces from Mrs. Parker's strange comments that Mr. Parker molested his daughters, and goes to San Francisco in search of Alison. Mr. Parker comes inside the house and threatens Alison, but Meredith holds him at gunpoint. He escapes when Billy bursts through the door. Billy becomes angry when Alison agrees with Amanda's advice and decides to prosecute her father instead of going to Las Vegas to elope. Jake breaks up with Amanda and decides to spend time on his boat. He takes in a beautiful woman named Brittany, who had jumped overboard following an argument with her abusive husband.