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#7: Why I Love Older Women (February 15, 1993)
Think the term "cougars" was invented for Ashton and Demi? Think again! Oprah tackled the topic of older women who date younger men back in 1993. In the show—which included a phone call with Cher—a guest named Vinnie had the quote of the day: "It's the difference between riding in a Volkswagen and a Cadillac," he said. "If you want to ride in a Volkswagen, go ahead. If you want the Cadillac, go for an older woman."