Nikki (Ashton Kutcher) is a player who has found a way to win at his game. With his good looks as his best asset, he has found a way to sleep his way into a life of privilege. His latest conquest is middle aged lawyer Samantha (Anne Heche), and he lives with her in a posh home in Hollywood Hills. Things are going great until Nikki meets Heather (Margaraita Levieva), who he soon discovers is playing the same game he is. They begin a game of trying to one-up each other at every turn. When Samantha discover's Nikki's infidelity, she kicks him out. As Nikki's relationship with Heather continues on, they both find themselves feeling things they haven't experienced before in their lives of game playing. Will Nikki and Heather decide to give their relationship a chance, or will the lure of their game be too much to let go?