I could've sworn Ashton Kutcher was done with the mid-20s slacker roles, but I guess he decided to squeeze one more in before he was too old to. In the indie rom-com Spread, he plays a bedhopping playboy with a loaded sugar mama (Anne Heche). He can have any girl he wants, buy anything he wants, and do anything he wants...except when it comes to a beautiful diner waitress who refuses to take his shit. If he's the poker champion of Nevada, then she's the poker champion of the world. He can never call her bluff and the girl's got game for days. She has him waiting at the phone for a callback. Whipped!!
You've probably already seen the manwhore-turned-monogamous bit more than once (i.e. Good Luck Chuck, How to Lose a Guy in 10 Days, etc.), but this film stars the criminally under-utilized Sebastian Stan ("Kings") and the sultry seductress Margarita Levieva (Adventureland), so it's at least worth the rental fee.