Duane Ruiz is out of college and out of options. Down on his luck, he has to choose between responsibilities at work and home or competing in the high-stakes Burning Rubber Wallball (AKA NYC handball) tournament.

After their regular babysitter cancels, the Thompson family turns to her friend, Anna to supervise their children while the parents go out to celebrate their anniversary. At first Anna seems like a dream come true to the kids, allowing them to eat extra cookies and play with things that are usually off-limits, but as her behaviour becomes increasingly odd, the kids soon find out that her intentions are dark and twisted—and she is not who she seems to be.

Fioravante decides to become a professional Don Juan as a way of making money to help his cash-strapped friend, Murray. With Murray acting as his "manager", the duo quickly finds themselves caught up in the crosscurrents of love and money.