In 1986, documentary filmmaker Ross McElwee made Sherman’s March, an epic deadpan journey through the American South, drawing a comic parallel between his romantic conquests and the destructive path made by the Union general. Now, 25 years later, Josh Freed begins his own first-person camera-march through love lost and found but with a decidedly Jewish twist. Freed opens his comic essay with home video footage of his Chicago bar mitzvah. Oddly inspired by his adolescent obsession for Louis Malle's My Dinner with Andre, the 12-year-old bespectacled boy toasts himself in an on-camera rant of self-loathing. Eventually, his insecurity and love for the movies lead him to pick up the camera and record his sometimes-embarrassing misfires with women. Freed’s filmed efforts at commitment falter until he meets the incredibly adorable and wise second-grade teacher Paulina, who sees through Josh’s act but finds herself falling for him anyway. The sad and funny fact that Josh cannot understand what she sees in him—the classic Groucho conundrum of not wanting to join any club that would have him as a member—lies at the heartbreaking core of the film. Five Weddings and a Felony is a freewheeling portrait of friendship, family and love that manages to be charming, galling, funny, cringe-inducing, and always compelling.