Youth in Revolt (2009)

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Shy, girlfriendless Nick is caught between separated parents with younger lovers. His father George has a toy girl, Lacey, while his domineering mother Estelle seems blissfully happy with beer-swilling lout Jerry. Sheeni Saunders sweeps into the teenager's life and Nick is completely smitten, resolving that the beautiful stranger is the one young woman capable of popping his cherry.