Enemies of Laughter (2000)

Nerdy-looking Paul is a neurotic, failed sitcom writer, with a lackluster love life. But his best pal has an idea that might turn things around when he decides to film Paul’s life, and turn his romantic disasters into a comedic documentary. When a beautiful young director decides to produce the real-life romantic comedy, Paul realizes that Cupid may be poised with his bow and arrow.