A surprise visit from Ben and Kate's father prompts Kate to start asking tough questions, leading to a big fight between her and BJ. Meanwhile, Ben teams up with Tommy to confront another deadbeat parent.
Ben grows concerned about the future of Rail Mall when his new business partner starts bringing in more associates to expand their plan. Meanwhile, Kate learns that Will has started dating again; and BJ and Maddie go to a commercial audition as mother and daughter.
Kate takes action after Maddie fails a test to get into the gifted program at her school. Elsewhere, Ben encounters a friend from college who stole one of his business ideas; and BJ's mother (Jane Seymour) visits town.
Kate has a hard time taking Will seriously after she sees the face he makes while playing guitar in his cover band; Tommy hooks Ben up with a job at the country club; BJ goes to a support-group meeting and gains insight about her friendship with Kate.
Kate attends a high-school reunion the night before Thanksgiving, and Will suggests that she stand up to a woman who bullied her when they were students. Elsewhere, Ben and BJ are keeping a secret from Kate.
BJ helps Kate find a costume to wear to an attractive neighbor's Halloween party. Meanwhile, Ben and Tommy stay home and hand out candy in hopes of meeting women, but the evening goes in an unexpected direction when Tommy accidentally eats some of BJ's "special" candy from Amsterdam.
Ben throws Kate the 21st-birthday party she never had. He invites her high-school friend Molly to the bash, but Tommy isn't happy about the additional guest. Meanwhile, Ben discovers that his ex-girlfriend Darcy is moving into his former dream home with her new husband.
Ben and Kate discover a list from an unfinished scavenger hunt that their dad created 15 years earlier, and they set out on a mission to find the remaining items. Meanwhile, BJ asks Kate for help retrieving her things from a former beau's home.
Comedy series about Kate, a straitlaced single mom raising her young daughter with assistance from her new houseguest, older brother Ben, who's a young-at-heart dreamer. In the opener, Kate prepares for a first date with help from a coworker, while Ben reunites with his childhood buddy, and together they try to stop Ben's ex from getting married.