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.