Nikki (Ashton Kutcher) has made a career out of targeting older women and using them for anything and everything … in exchange for a little sex. But the player gets played when he meets Heather (Margarita Levieva), a pretty waitress who knows every trick. Before Heather came along, Nikki had a foolproof arrangement with Samantha (Anne Heche), a successful attorney who was happy being “friends with benefits.” But now he might actually be in love.