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12-Mar-2015 05:08

Despite all the criticism that followed the two up until her 18th birthday this year, Kylie has yet to find a problem with the 7-year age difference.Demi has a long rep for dating up when it comes to her men (cue Joe Jonas and Trace Cyrus).Her strangest rumored relationship being with Matthew Morrison.Her most ongoing relationship, though, has been with her oldest beau, Wilmer Valderrama, who is actually 12 years older than the “Confident” singer.The Scream Queen star built herself quite the rep for dating her older co-stars during her Glee days.Yet, despite the obvious overflow of eye-candy in their own social circle, all of the bachelorettes on this list have always had their eyes fixed on older men—even if it was under somewhat-illegal circumstances.So in case you’re Considering it was technically illegal for there to have even been an alleged relationship between the 24-year-old Tyga and then-17-year-old Kylie, we obviously underestimated his sense of dignity.

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As long as men and women have existed, men have desired women younger than themselves.All of biology and society is tilted in this direction, whether it's the fact that men remain sexually potent far longer than women do or the squishy idea that men become "distinguished" as years go by while older women look, well, "old." Hey, we didn't write the rules, we're just teling you how it is.Let's face it: Hugh Hefner is a freak, in the most enviable way possible. We may never see someone quite like Hugh Hefner again, but that doesn't mean cradle-robbing isn't a popular practice for men.And seeking mates with that father-figure quality (evolution makes them want reliable providers, y'know) continues to occur in the female of the species.

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In June 2011, Hugh Hefner's then-fiancé Crystal Harris, 60 years younger than the aged playboy, skipped out on the wedding and said some not-very-nice things about her (apparently) heartbroken old beau.

A year later, the two reunited, and on Saturday, the news broke that they again planned to wed, this time in a small ceremony to be held on New Year's Eve at the Playboy Mansion.

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