Jo, Alison and Billy go to Steve's ranch for the weekend. Billy is unhappy about Steve's attraction to Alison. Jo declines to sleep with Steve because she realizes that she hasn't gotten over Jake. Steve admits that he is also harboring feelings for someone, and suggests that they break up. Jo confronts Alison after deducing that she is the one for whom Steve is pining. Steve and Alison later share a kiss. Jake forms a friendship with Palmer and tries to get Amanda to open up about her childhood. Jake suspects that Palmer is engaging in fraud. Michael convinces Kimberly to stay at the hospital instead of moving back to Cleveland, and promises to remain professional.

Alison learns that Steve is leaving for Europe in a few days. He gives her a new jeep and confesses his feelings. Alison joins him for a weekend on his ranch, but suddenly dumps him because she wants to reconcile with Billy. Billy's bitterness about Alison clouds his judgment on a writing assignment. Jake forces Palmer to confess to fraud on tape. Palmer convinces Amanda that Jake set him up, so she dumps Jake and plots to evict him. Michael falls out of bed, and Sydney refuses to help him until he apologizes for his past actions. Jo rejects Jake's thinly veiled advances, but Billy and Amanda sleep together.

After Michael shuns her, Sydney tells Jane the truth about her involvement with prostitution and Michael's scheme against Robert. Jane blames herself for Sydney's problems, and throws Michael out. Sydney is acquitted because of an incompetent prosecution team. Jo is angry when Reed approaches Amanda as a potential investor in his charter boat service. Jake confronts Reed about his intentions toward the two women in his life. Billy wins a promotion, but learns that the job requires a move to New York. Matt is annoyed by the bizarre behavior of his new love interest. He learns that the man is a closeted Navy officer.

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

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.