Ryan Legrand, along with his partner Dean, runs a private investigation firm that specializes in matrimonial cases. Ryan's investigations have made him a drab cynic regarding relationships, making him unwilling to share his feelings with a woman. Joining a video dating service, Ryan feels, may force himself out of his shell and help him to meet women. Through the service he meets struggling actress Tura. He is attracted to her, but they have a falling out after a disastrous weekend with her friends, and Tura decides to keep him at a distance. Crestfallen, Ryan reacts to her rejection of him by doing what he knows best -- setting up a video surveillance of her every move.