Crazy, Stupid, Love. (2011)

Cal and Emily have been married for over 20 years. But when Cal learns that Emily had an affair he moves out. He would then go to a bar and whine about what happened. Jacob, a regular at the bar, upon hearing his woes offers to help him. By giving him a makeover and teaching him how to be a player. It isn't long before he's picking up someone frequently. But eventually he realizes he still loves Emily and wishes he could go back. At the same time his son is nursing a crush on his baby sitter who doesn't feel the same way. And even Jacob gets a new outlook when starts to feel something about a girl he tried to pick up earlier, but turned him down because she has a boyfriend.