Jack Day is the prototypical attorney -- except that he hates practicing law. His wife Abby, has recently reentered the workforce and been promoted to creative director of a major Philadelphia ad agency. Jack and Abby have three kids: Natalie, a straight-A student, soccer star and prom queen; Cooper, a sometimes dark and insightful teenager who takes the family's pulse on a daily basis from his edgy perspective and Nathan, an nine-year-old genius who suffers panic attacks.

Jack is unable to decide what to do next about his career and his life. Abby is livid when her boss hires her old flame. Meanwhile, Natalie struggles with her transition from "with-it" teen to "with-child" object of scandal at school. Also, Abby's hot under the collar after her former flame lands a job at the agency. Lastly, Cooper wins a national writing contest and attracts the attention of an older woman.

Jack goes to see a psychiatrist at his old job for an evaluation to get his job back. Cooper considers tearing up his story and staying with Emma. Natalie must make a decision that will affect the future of her baby. Lastly, Jack goes for a night out with his friends and old co-workers.