Sarah Michelle Gellar stars as every man's fantasy in this edgy thriller that explores madness, greed and sexual experimentation. Cindy and Alan (Adrian Grenier) should be the perfect Harvard University couple. She's a sexy cheerleader; he's a driven philosophy student and star of the basketball team. But all is not what it seems because Cindy, a master manipulator of men, is also the daughter of a local Mafia boss and Alan spends his time experimenting with drugs. So he hardly knows what's happening when Cindy involves him in a million dollar game fixing scam that would make her mob daddy proud. With the help of his insatiable philosophy professor Chesney (Joey Lauren Adams), Alan is going to have to get his head together, dodge FBI agents and mob goons and find a way to turn the tables on Cindy before time (and his luck) runs out.