Dan and Carter are both facing challenges in their personal lives. Dan is supporting two daughters—16-year-old Jana (Zena Grey) and 18-year-old Alex (Scarlett Johansson) who is preparing to enter college—and learns that his wife is pregnant with their third child. Meanwhile, Carter is dumped by his adulterous, narcissistic wife of seven months and focuses all of his energy on work. With Dan facing the financial realities of taking out a second mortgage, to cover his daughter's college education costs, and a new child, and with Carter needing Dan's practical, real-life experience in the field of advertising, the two form an uneasy friendship.