Andy and Jim work together on the "Chef-A-Rooni" account at the ad agency. They learn a deep, dark secret about the American advertising business.

Andy, Kevin, Jim, and Posey take a road trip on Memorial Day Weekend. But even as the trip progresses, they are unable to agree on their destination. Meanwhile, Gus and Wally take care of Stogie.

Andy and Gwen's relationship goes through a rocky period when Andy starts dating Jim's assistant Stacie.

Kevin sinks to his lowest point ever when he pretends to be a terminally-ill boy in order to get a guaranteed admission to Yale.

Kevin accidentally appears in the background of a porno movie being filmed in the building. When his parents find out, Kevin is out of Mission Hill and living with his parents in Wyoming, but he's a different person after his time in city.