If you're a man and you're not very good at it, check out the wonderful stories directed by John Cassavetes. He was a brilliant independent film maker and sort of spearheaded the idea of independent film in America. His movies tend to revolve around the themes of the dark sides of masculinity ā aka guys being dudes (derogatory). His films were also his own various insecurities, both personal and professional, made naked on screen.
Please check out Husbands, The Killing of a Chinese Bookie, and A Woman Under the Influence. These aren't typical independent films (i.e., they're not black and white and 4 hours long). They're profoundly unpretentious yet are deeply thoughtful all the same.
John Cassavetes ā truly a brilliant and underappreciated director.