Alison's roommate leaves in the middle of the night and sticks her with the rent. Faced with eviction, she takes the goofy Billy Campbell up on his offer. Jake attempts a relationship with Kelly Taylor and 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 gets a job as a cab driver and makes a connection with a passenger, who he begins dating. Alison is put off by the speed of the couple's courtship, and grows tired of their constant presence in the apartment. Jake is arrested following a scuffle at the unemployment office, and is less than grateful when Kelly bails him out. Jane worries about the status of her marriage when Michael is unable to recall the specific moment he fell in love with her.

Jake fears that Kelly will be hurt if they continue their relationship and sets up a fake date with a friend to trick her into breaking up with him. Jane is depressed when Michael must work instead of spending a romantic evening with her. Billy completes his first screenplay, but Alison is decidedly less than impressed.

Alison is befriended by a guy from the mail room, who quickly asks her out and reveals that his father is the vice president of a sunscreen company with which D&D is doing business. After failing miserably in his new job at a coffee shop, Jake agrees to help his ex-girlfriend Peri with the sale of a fraudulent painting. Matt questions Rhonda's character after she reneges on a promise to help with a dinner at the halfway house.

Jane learns that she is pregnant, but doesn't tell Michael because he hadn't seemed thrilled by the prospect of having kids. Billy is given a column in the neighborhood newspaper.

Jake asks Alison to help him study for his G.E.D, but requests that she keep the matter a secret. When Rhonda meets up with an old friend from her dancing days, she is haunted by memories of the injury she faked to avoid an audition.

Billy loses his job and asks Alison to accompany him on a visit to his parents. Sandy gets a swelled head after landing a part in a horror movie, and ends up moving out. Michael and Jane discuss their excitement and anxiety about the upcoming birth of their baby.

While Sandy is shopping with Rhonda, she meets a new guy who asks her out. However, she soon realizes that there is no spark between them and tries to let him down gently. Meanwhile, Alison looks to replace her clunker car but has a hard time letting go because of all the memories it holds.

Billy helps a woman whose car has broken down along the side of her road. Jake and Sandy try to rebuild their relationship, agreeing to go on a platonic date where things quickly get out of hand.

During his surprise birthday party, Jake receives an unexpected visit from his mother. Billy is the victim of a car-jacking after dropping off a passenger in South Central, and begins to display signs of racial prejudice, making Rhonda is furious. Jane and Michael quarrel after he behaves insensitively during a parenting class.

Jane gets bad news at a routine appointment. Michael is reluctant to express his emotions about the bad news, and quarrels with colleague Kimberly Shaw when she tries to convince him to show his feelings.

After a chance meeting in the street, Alison becomes romantically involved with environmentalist Keith Gray. 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.

Alison continues to see Keith, despite the misgivings of her friends and the fact that her erratic behavior has put her job in jeopardy. Matt is the victim of an attack outside a nightclub. A customer at Shooters asks Sandy to audition for a soap opera.

Keith stays with Alison while his estranged wife, Lily, is in town for the weekend. Rhonda's new roommate turns out to be completely anal-retentive.

A mysterious aspiring photographer named Jo Reynolds moves into the building. Michael and Jane begin spending time with a respected pediatrician and his wife.

When Jo hits financial hard times, Jake offers to help her. Meanwhile, Jane loses her job and Matt continues his legal threads.

Jake is visited by a former girlfriend and Alison falls ill. Meanwhile, Rhonda meets a wealthy restaurant owner.

Alison undergoes successful surgery and Billy agrees to care for her when she returns home from the hospital. Jo and Jake try to overcome their unhappy memories of Christmas. Michael is depressed when he and Kimberly cannot save a young gunshot victim.

Jane receives a surprise visit from her sister Sydney, who has dropped out of college. Billy agrees to set up Alison with one of his friends. Jake tries to prove himself by taking up one of Jo's interests, poetry. Rhonda is furious when Terrence doesn't defend her to his snobbish friends.

Sydney continues to get on Jane's nerves and Jake reluctantly tells Jo about his meeting with her husband, Charles.

Alison is promoted to junior account executive and meets art director Amanda Woodward. Billy doesn't hit it off with a blind date arranged by Michael, but is attracted to Amanda. An overwhelmed Rhonda breaks her engagement.

Amanda, Billy and Alison spend the weekend at a lakeside cabin, while Jake and Jo have a romantic evening together. Matt is caught in the middle of Rhonda and Terrence's romantic problems.

Alison remains irritated about Billy's relationship with Amanda. Jo's husband offers her a $50,000 divorce settlement, but she wants to turn it down because of her pride.

Billy backs out of plans with Alison to have dinner with Amanda and her father. Jake objects to Jo's attempts to help with the business.

Billy and Amanda bicker constantly after he moves in with her. Michael's college friend makes a pass at Jane after they have dinner together.