After five years of marriage, T.I. and Tiny decide to celebrate with a trip to Costa Rica. However, when the family catches wind of this planned getaway, T.I. and Tiny feel the pressure to make it a family vacation.

A longtime friend of the family, Crow, seeks T.I.'s expert advice and guidance in obtaining some female companionship. T.I., who willingly accepts the task, learns that with ol' Crow, it'll take more than a makeover to help his needs.