After drifting apart, the goofy older brother Ben decides to reconnect with his practical single mother sister Kate and moves in with her and her six-year-old daughter, Maddie.
As Ben adjusts to Kate's home, Kate asks him to be more strict with Maddie. Kate's plan to get Maddie into a better school backfires.
When Kate and Ben find an old envelope with questions for a traditional Fox family scavenger hunt, Kate teams up with BJ as she sets out to beat Ben.
Ben gets mad after finding out that his ex-girlfriend Darcy is moving into her parents’ house after she got married. Ben throws Kate a belated 21st birthday party, where she reunites with her old college friend, Molly.
Ben gets angry that Kate overreacts to every minor injury that happens to Maddie, so he tries to prove to her that she can't plan for every situation. Louise shows up in Ben's life.
As Halloween arrives, Ben tells Kate that he gets scared less easily than her, since she's always prepared. Things get out of control when Tommy gets high after he eats BJ's special candy. Kate connects with the single dad, Will.
Ben desperately tries to find a job to impress his niece Maddie at her school's career day. BJ clashes with the bar staff for being rude to them.
Will tries to help Kate confront her fears when she relives unpleasant memories from her high school days.
Kate feels awkward as she gets turned off by Will's expression while he's playing the guitar. Ben works with Tommy at the country club. BJ feels ignored by Kate.
As Ben tries to sabotage Kate's relationship with Will, he goes with them to a camping trip. Tommy meets Lila while she's walking her dog.
Ben learns that his old college roommate stole an idea of his and he's now a wealthy man. BJ gets a surprise visit from her mother. Kate helps Maddie with her "B-Squad" classmates.
The businesswoman Vera helps Ben with his new business idea only to get close to him. Kate's effort to be friends with Lila backfires.
After breaking up with Will, Kate tries to distract herself by taking a cooking classes. Ben encounters problems with Vera's associates regarding his Rail Mall idea.
When Ben and Kate's father comes for a visit, Ben tells him about all the things he didn't get to do with him. Their plan to go fishing takes an unexpected turn. Kate's attempt to succeed at something fails.
After Kate helps her father Randy with his business deal, Ben feels left out. He decides to prove that he's better than her by organizing the annual PTA dance at Maddie's school.
As Kate returns to college, she decides to focus on her studies instead of boys, until she falls for her ethics professor. Ben is planning to celebrate his two-month anniversary with Vera, but she's upset with his childish behavior.