Happy Hour (2006)

Henry Beckman left his ideal life in Missouri to movie to Chicago with his girlfriend Heather to work in her family's business. But in the course of one morning, Henry loses his girlfriend, his apartment, and his job. In his vulnerable state, he meets his new roommate, the vain, flashy, and lovable rogue, Larry Cone, and then goes to work for Larry's childhood friend, Amanda, a beautiful mess who's unsuccessfully trying to emulate her idol, Kelly Ripa. Larry is in need of someone new around to listen to his theories about life and women after his best friend and former roommate got, Brad got engaged to Tina, a cold, controlling woman who has nothing but contempt for Larry.