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May 5, - A reversal of the classic May-December romance often throws people for a loop. Do relationships between older women and younger men work? . be upfront about her feelings if she wants it to turn into more than just sex. Jun 3, - Best of Older Women - Younger Men/Boy Romance in Movies. This is a list of mainstream films featuring significant 'May–December' romances, .. sex with Cougars — older women looking to have sex with younger men.