Life imitates art—and sometimes hilariously so. Mila Kunis and Ashton Kutcher, stars of Friends With Benefits and No Strings Attached, famously ignored the movies’ cautionary tales, ending up married with kids after just months of “no strings attached” fun. They weren’t alone: Bradley Cooper once lived that college-era fantasy with his best friend, Dyan Cannon openly dates “friends with benefits,” Fran Drescher has a rotating crew, Florence Henderson found comfort in companionship after her husband’s death, Sonja Morgan had a discreet fling in her fifties, and Matthew Perry nearly proposed to Lizzy Caplan after six years of “friends with benefits.” The movies got it wrong—real life? Often, way more complicated and surprisingly sweet.

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