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