Jane learns that she is pregnant, but doesn't tell Michael because he hadn't seemed thrilled by the prospect of having kids. She tries to get an abortion secretly, but changes her mind. Michael is furious at Jane for keeping him in the dark, until the joy over their child brings them back together. Billy is given a column in the neighborhood newspaper. He can't come up with a topic because his life is boring. Hoping to alleviate this problem, he convinces Jake and Matt to go bungee-jumping with him. After he is unable to go through with the jump, Billy writes a column about ""wimping out.""

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.

After a chance meeting in the street, Alison becomes romantically involved with environmentalist Keith Gray. She is stunned to learn that he is married, but finds it difficult to break off the relationship after he vows to leave his wife for her. Billy is saddled with bad credit because he has yet to pay off a college loan that he didn't even need. Jane is determined to work off the weight from her pregnancy. She realizes that she is trying too hard to forget the miscarriage.

Billy's father dies of a heart attack. Amanda tries to exploit Billy's vulnerable state to seduce him, and then shows up at the funeral in an attempt to score points with her ex. Alison flies back from Seattle to comfort Billy. Billy feels that he let his father down, and decides to take over the furniture store. His mother says that she has sold the store to the employees, and that she wants Billy to use his writing gifts. She gives Billy a letter in which his father expressed his pride in him. Billy drives Alison to the airport, but she decides to move back to Los Angeles. Michael tries to convince Kimberly to move in with Billy, but she declines. She explains that seeing the death of his father reminded her of how much involvement she would have in his life if they were roommates. Michael lies about going to the hospital and instead helps Kimberly with a plumbing problem. She offers him dinner and tries to come on to him, but he resists. Billy's family tragedy prompts Matt to

Kyle finally saves Eric after he admits that he didn't sleep with Amanda. Kyle rejects Amanda's reconciliation attempt, as he feels he can no longer trust her. Eric returns all of the businesses so that Kyle will believe that he slept with Amanda after all. Kyle punches out Eric before he can leave town, then gets drunk and sleeps with Taylor. Michael interrupts Brett's vigil for Megan, and takes the credit when she recovers. Craig pines for Jennifer. Samantha gets into an argument with Billy's mother before the wedding. Billy and Sam patch things up after exchanging vows. Brett tips off Peter about Lexi's pill addiction.