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Will Henry (Jemaine Clement) is a novelist and teacher in New York. At his twin girls’ fifth birthday party, Will’s life is turned upside down when he walks in on his girlfriend and the mother of his children, Charlie (Stephanie Allynne), with their friend, Gary (Michael Chernus). One year later, Will is still alone and trying to put his life back together. He finds unexpected challenges when one of his students tries to set him up with her mother, Diane (Regina Hall).