Louise, an unfulfilled divorced woman with regrets, gets the chance to relive her past when she meets a young man who bears an uncanny resemblance, in name and appearance, to her high school sweetheart who died many years before.

A smooth-talking ad executive attributes his remarkable success with women to his ability to manipulate their emotions from the moment he first meets them. When his teenage nephew drops in for a visit, he soon learns that his approach isn't as foolproof as he thought when he attempts to teach the boy how to pick up women.