Kimberly Stewart is at the mercy of her mother, Alana, who is trying to find her love; Ashley Hamilton returns to his roots and attempts a second shot at music; George Hamilton learns that his teenage son GT is no longer in virgin territory.

Kimberly takes Sean on a charity trip to Haiti to get some perspective on life; Ashley attempts to break from his co-dependency on his best friend for the sake of his new relationship; George takes Pablo and GT on a Vegas adventure.

Kimberly and Sean continue to argue over Sean's reluctance to find perspective in Haiti; George attempts to teach GT not to be in such a rush to grow up; a sober Ashley is crushed when he learns about his girlfriend's smoking habits.

Kimberly is afraid Dean might have feelings for her and tries to set him up with a friend; Sean talks GT into taking George's Bentley for a joy ride.

Kimberly invites Ali on the family holiday, Sean has a birthday party for his dog Duke, and GT makes a bad joke that goes very wrong.

The family goes to Palm Springs where trouble starts between Alana and Kim; tensions rise between Ashley and Ali when Ali sneaks out to a bar; George urges Kimberly to make G.T. feel included.