Ben continues to expand his "Rail Mall" idea with his new business partner, Vera, but when she brings in more associates to help expand their plan, Ben doesn't like the direction in which it’s heading. Meanwhile, after finding out that Will has been dating since their break-up, Kate goes on a date with a baker she met at Will’s party. Also, BJ and Maddie pose as mother and daughter for a commercial audition.

Tommy finally brings around his new girlfriend, Lila, to meet the gang. But when Kate suggests the two women get to know each other, things don't go as planned. Meanwhile, Ben moves forward with his "Rail Mall" business plan.

When Maddie fails the test to get into the gifted program at her school, she becomes part of "The B-Squad." Kate, who blames herself for Maddie's failure, decides to take matters into her own hand and gives The B-Squad an unforgettable experience. Meanwhile, Ben runs into an old pal from college who stole one of his business ideas, and BJ's mother, Wendy, comes to town and gets a surprising introduction to Buddy.

Although Ben, BJ and Tommy disapprove, Kate and Will take their relationship to the next level when they go on a romantic camping trip together. Of course, the trip quickly goes awry when some unwelcome guests decide to tag along. Meanwhile, BJ makes it her mission to help Tommy move past his feelings for Kate.

When Kate sees the face that Will makes while playing guitar during his cover band's performance, she gets turned off and unable to take him seriously. Meanwhile, Tommy gets Ben a job at the country club which soon backfires for both of them, and BJ attends a support group where she gets good advice about her friendship with Kate.

When a high school reunion is held on the eve of Thanksgiving, Will (guest star Geoff Stults) encourages Kate to attend and stand up to the high school bully, Anna (guest star Amber Stevens) for giving her an unforgettable nickname. Meanwhile, in the midst of the holiday season, Ben doesn't think he can keep much longer the huge secret that he and BJ have been hiding from Kate.

With Career Day at Maddie's school coming up, Ben wants to find an actual job so he can make his niece proud. Meanwhile, Kate starts to develop a crush on her neighbor Will, and BJ face backlash from a co-worker at the bar for getting a raise.

Kate gets invited to her hot neighbor's Halloween party, so BJ tries to help Kate break free and be someone completely out-of-character for the night. Meanwhile, Ben and Tommy decide to stay home and hand out candy to the trick-or-treaters in hopes that they'll meet some hot moms, but the night takes a turn when Tommy unknowingly eats some of BJ's "candy" from Amsterdam, and Kate bonds with Will (guest star Stults), a single father.