Mason falls into ad-campaign trouble when he makes a promise to a client that he might not be able to keep. Mason also consults his teen daughter about what's cool in the youth market---but he soon discovers his daughter is far from typical. Meanwhile, Hector and Tom battle over who will squire Sarah to a party.

The ad group networks to score a coveted account for Chicago's Olympic bid. Mason plans a long weekend with Erin at a ritzy Chicago hotel, so he grudgingly gives Conner managerial control over the group. Meanwhile, Sarah lands a new partner who had earlier bowed out of the ad business to have children.