Flora Diaz in Roger Dodger (2002)

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Cambell Scott is Roger Dodger (2002), and when the film opens he's getting the blow-off from his boss and ex-lover, Isabella Rossellini. Then his nephew arrives in town, and Scott decides to get the virgin laid. They hit the singles bar and nearly score with a pair of sophisticated sweeties, Jennifer Beals and Elizabeth Berkley. Then the nephew has an opportunity to bang a passed-out drunk at a party, only he's too good of a guy. Finally, Scott takes the chump to a whorehouse, where the pink stuff is spread eagle and open for the taking. Does he take it or does Scott redeem himself? Now, what would Mr. Skin do?