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You're a Big Boy Now (1966)

Synopsis:
Bernard Chanticleer's father gives him two simple words of advice: "Grow up." Bernard knows that his first step is to find a girl who's "willing," but he passes up a sure thing, Amy Partlett, for a more elusive goal. Her name is Barbara Darling, an inscrutable go-go dancer. More than a few obstacles keep Bernard from his dream world. There's his doting mother, who mails him locks of her hair and weeps at the thought of her baby as a man; there's a malicious rooster, trained to attack pretty girls, patrolling the halls of his New York City rooming house; and most of all, there's Barbara herself. She turns out to be a man hater, emotionally scarred by the lecherous wooden-legged hypnotherapist who "counseled" her in high school. All in all, Bernard finds himself in an improbable universe with a calculated clumsiness designed to evoke his confusing coming-of-age.
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