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.

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.