This is Not a Film (2003)

In a broken attempt to find a woman who has broken his heart a Manhattan shoe salesman fearlessly throws himself into the world of guerilla filmmaking creating a modern day message in a bottle actually a videotape hoping that someone seeing it maybe you will know his exgirlfriend To help the viewer understand who he is and why his girlfriend left him this neophyte filmmaker hires a temperamental actress to play his ex and together they reenact scenes from his failed relationship During the course of filming Michaels mistakes blunders and inadequacies as a boyfriend are mercilessly pointed out to him This Is Not A Film is a romantic comedy about making a mistake and recognizing it in the most painful way possible by making it all over again