In the early 1960s, teenager Adam Stafford (Cameron Bright) becomes obsessed with his new neighbor, Catherine Caswell (Gretchen Mol), a divorcée and free spirit. Stafford spies on Caswell as she meets with strange men, and, despite the warnings of his conservative parents, he begins working for her as a gardener. Amid rumors of her affair with President Kennedy, the two become close, but political intrigue surrounding her acquaintances soon infringes on their friendship.

Mutual friends Barbara and Genevieve are both sleeping with District Attorney Sam Brady. When they become aware of their bizzare love triangle, they plot against him.