Thirtysomethings Theo (Chris Messina) and Nat (Rashida Jones) are engaged to be married. They live what seems to be on all counts a comfortable life of love, music, and laughter in their cozy Brooklyn apartment. But Theo is bored with his job as a wedding photographer—the generic backgrounds, the artificial posing, the stilted newlyweds—so he develops the unconventional side business "Gumshoot," a service where clients hire him to secretly stalk them with his camera.
When he is called out on a job to snap pics of an exhibitionist mystery woman (Meital Dohan), a simple gig develops into a voyeuristic obsession that forces Theo to confront uncomfortable truths about himself and his impending marriage.
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