This is Not a Film (2004)

Sinopsis

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 ex-girlfriend. 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, Michael's 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.