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The Theory of Flight(1999)

DramaComedyRomance1h 41m6.2

A dreamer who aspires to human flight is assigned public service after one of his attempts off a public building. This leads him to meeting a young woman, who is dying of motor neuron disease. The strong-willed woman admits her wish to be de-flowered before her death. The man, struggling to maintain his relationship with his girl friend, declines but offers to help pay for a gigolo to do the deed. The following events play off the inherent comedy and drama of the circumstances.

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Looks like this movie is more elusive than Bigfoot. Can't find it anywhere to stream.