Sol Goode (2001)

Sol Goode, a charismatic L.A. twenty-something, has always relied on charm, good looks, and fast talk to glide through life. But his luck may have run out; faced with eviction from his hipster apartment, totaling his car, and the threat of having to find a real job, Sol realizes that maybe the life he's been leading is no longer making him happy. Through this self-examination, he finds that being a womanizing hustler is an unfulfilling life and he will truly be happy with his best friend Chloe, who, unfortunately, knows him all too well. The result is a wickedly funny, heart-felt story as Sol tries to win her over.