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.