How I Got Lost (2009)

Two friends deal with loss amidst events bigger than them. Andrew is the friend we all have, the one who convinces you to come along despite your better judgment. Talented but with seemingly nothing to lose, his tailspin is balanced only by his professional drive to succeed as a trader on Wall Street. His best friend Jake, broken-hearted and writing sports instead of fiction, does his best to clean up the mess his friend creates until he runs into his capricious ex, Sarah again. So Andrew convinces him to ditch New York and hit the road, going nowhere.