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Restless 17-year-old Sebastian Cole (Adrian Grenier) is living in Dutchess County, N.Y., in 1983 when his stepfather, Hank (Clark Gregg), announces that he plans to live life as a woman named Henrietta in this unusual twist on a coming-of-age tale. After spending several months away in England, Sebastian shows up on Henrietta's doorstep looking for much-needed stability in his life and hoping to expand his worldview while finishing high school.