This show follows some siblings and their friends while they explore the boundaries of their comfort zones.
Ben settles in to Kate's place. To get Maddie into a better school district, Kate lies about where she lives. This lie falls apart and she has to go tell Maddie's principal the truth. Kate thinks Ben should be more strict with Maddie.
When Ben discovers that Kate never had a big 21st birthday blow out because she had Maddie, he decides to turn her 26th birthday into the party she never had. One of Molly's old wild friends Molly comes in to town for the party, much to the dismay of both Tommy and BJ.moreless
Kate thinks that she is prepared for any emergencies so Ben puts her to the test. Meanwhile, BJ decides to go out on a date with her boss.
Kate tries to work up the nerve to ask out her attractive neighbor during a Halloween party. While he and Ben stay home to give out candy, Tommy accidentally eats some of BJ's special candy from Amsterdam and begins to hallucinate.
Kate is taking things slow in her new relationship with single father Will but Ben constantly interferes to test Will and see if he is worthy ofdating his sister. Ben tries to find a career so he has something to talk about at Maddie's career day.
At an annualhigh school reunion party at the bar, Kate iseager to show offWill to all her friends and her high school nemesis.
Ben and Kate discover that Will is wealthy which causes Ben to act even stranger as usual and leads to him interfering on a romantic trip to his cabin. BJ tries to convince Tommy that it is time for him to move on from his crush on Kate and find a girlfriend.moreless
Kate is disturbed by the face Will makes while playing with his band. Ben gets a job at the country club with Tommy but may end up costing him his job. Feeling ignored by Kate since she started dating Will, BJ starts attending a divorced women support group.
Still hurting from her breakup with Will, Kate turns her attention to getting Maddie into the advanced placement program at school. When Maddie fails to make the program, Ben decides to take all the other kids that did not make it and start their own gifted program. Ben also discovers that an old college friend of his is now a success based on an idea he and Ben had while in school. BJ climbs back into a years long lie she puts on when her mother comes to visit.moreless
Kate decides to try and befriend Tommy's new girlfriend Lila but messes things up when she mentions Tommy's crush on her. Meanwhile Ben tries to find a CEO for Railmall but the woman he finds may only be helping him for sexual favors.
Will invites Kate to a party at his house and, while he soon attempts toget back together with her, sheends up finding romancewith Lance, a baker who is more than willing to take on the her crazy life and friends.Ben and Vera's employees but heads on Railmall. BJ tries to pass Maddie off as her own daughter during an audition for a commercial.moreless
Randy focuses all his time on Kate, leaving Ben isolated. Ben volunteers to run the father-daughter dance.
Kate starts assessing the direction her life is going. Ben and his father, Randy, clash over Randy not teaching Ben how to do stuff as he was growing up.
Kate falls into the same trap with boys as she returns to college. Ben and Vera's two month anniversary is fast approaching.