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20 Older Celebrities Who Actually Dated Teenagers

Updated April 6, 2021 1.2m views20 items

Age is just a number, or at least it is to these celebrities who dated teenagers. It's not uncommon for celebs who work together to become romantically involved - and that doesn't exclude those who aren't quite legal. There are lots of famous people who dated teenagers, sometimes out in the open and other times in private. These folks found love sometimes in a controversial place, and sometimes it actually worked out.

From brief flings to tying the knot, some of these celebrities who dated teens ended up finding true love with people who couldn't yet buy booze. 

  • Who He Dated: April Love Geary, 19

    Shortly after the booming success of his single, "Blurred Lines," in 2013, Robin Thicke went through a weird spot. He started partying often, dealt with substance abuse issues, did that really creepy VMAs performance with Miley Cyrus, got sued for the unauthorized use of a Marvin Gaye track, split with wife Paula Patton, and then tried (unsuccessfully) to publicly win her back. 

    Shortly after Patton officially filed for divorce in 2014, Thicke was seen driving around in his convertible with 19-year-old model April Love Geary. Mid-life crisis officially complete. Two years later, they're still together, but we still need some space. 

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    • Photo: Gage Skidmore / Wikimedia Commons/CC 2.0

      Who He Dated: Maïwenn Le Besco, 15

      After his 1991 divorce from Nikita star Anne Parillaud, director Luc Besson, 32, started dating 15-year-old Maïwenn Le Besco. The couple married the next year, while Maïwenn was pregnant with their daughter. Besson later claimed that their relationship inspired his film Léon: The Professional (1994), which followed an emotional relationship between an adult man and a young girl.

      Besson and Le Besco were married until 1997, at which point he became involved with The Fifth Element actress Milla Jovovich, who was 22 at the time.

       

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      • Who He Dated: Mandy Moore, 16; Lindsay Lohan, 17; Demi Lovato, 17

        It might just be easier to list the celebrity teens Wilmer Valderrama hasn't dated. He dated 16-year-old Mandy Moore from 2001-2002 despite being four years her senior. At age 24, Valderrama dated 17-year-old Lindsay Lohan, though they kept the relationship a secret until her 18th birthday in 2004. They broke up a year later, inspiring her broken-hearted song, "Over."

        And in 2010, the 30-year-old began dating 17-year-old Demi Lovato. The two have been on-and-off since then, but are currently off. 

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        • Who He Dated: Taylor Swift, 19

          When 19-year-old Taylor Swift began dating 32-year-old John Mayer in 2009, the world did a collective head scratch. Less than a year later, Swift released the song "Dear John," on her album Speak Now, which not-so-subtlely panned Mayer with lyrics including, "Don't you think 19's too young to be played/ by your dark twisted games/when I loved you so?" Well said, Tay.

          Never one to remain silent, Mayer clapped back in a Rolling Stone interview, saying it was a humiliating and lousy thing for her to do to him. 

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