Kimberly Stewart finds herself at the mercy of her mother, Alana, and iconic ladies' man George Hamilton learns that his teenage son GT is no longer in virgin territory.
Kimberly attempts to improve Sean's perspective on life with a charity trip to Haiti; at the same time, Ashley needs to deal with a codependent best friendship in order to save his new relationship.
Kimberly is concerned that Dean could have a crush on her and she decides to set him up with a friend. Sean is able to convince GT to take George's Bentley for a joy ride.
Kimberly asks Ali along on the family vacation. Sean throws a birthday party for his dog.
The family travel to Palm Springs. Included: trouble brews between Alana and Kim; at the same time, Ali sneaks out to a bar, creating tensions between her and Ashley; and George urges Kimberly to make G.T. feel included.
Kimberly goes to Alana's hometown to get a better understanding of her mother; Sean fights to move on from his ex and start dating again; Ashley finally meets the fate of his new album.
Alana finally admits how she feels about George when he announces he's ready to settle down; Kimberly fights to reconnect with Ashley and Sean launches his business.