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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: Priscilla Presley, 14

    Priscilla Presley, now 73, was only 14 when she met 25-year-old Elvis at a party in Bad Nauheim, Germany. She was the daughter of a U.S. Naval pilot, and Presley was serving in the Army despite a successful music career. Priscilla's parents pressured the two to marry, and they tied the knot in 1967 when she was 21.

    While even hardcore Elvis fans have a hard time with the initial age gap, Priscilla maintains the two consummate the marriage until their wedding night. They had one daughter, Lisa Marie, and amicably divorced in 1973.

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    • Photo: Andrew Steinmetz / Wikimedia Commons/CC 2.0

      Who He Dated: Aaliyah, 15

      R. Kelly has certainly faced a lot of scrutiny for his alleged actions with underage girls, but back in the '90s he had an odd relationship with up-and-coming R&B singer Aaliyah. Kelly was introduced to Aaliyah as a "mentor" and he helped write and produce her first album, Age Ain't Nothing But A Number when she was 14.

      Despite denials from both parties that their relationship was platonic, the two secretly wed in 1994. The marriage was ultimately annulled as Aaliyah was not yet old enough to consent to a lifetime with the 27-year-old Kelly. Tragically, she passed away in a plane crash in 2001, so we can't hear her side of this story. 

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      • Photo: Gabbot / Wikimedia Commons/CC 2.0

        Who She Dated: Conor Kennedy, 18

        Taylor Swift dipped her toes into a younger dating pool in 2012, when the then-22-year-old dated JFK's great nephew, who was four years her junior. Their summer fling only lasted a couple of months, but it was long enough for Swift to receive a great deal of backlash for the age difference.

        The couple split because of the long-distance and Taylor moved down her now infamous list of romances.  

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        • Photo: Alan Light / Wikimedia Commons/CC 2.0

          Who He Dated: Shoshanna Lonstein, 17

          At the height of his Seinfeld fame in 1993, Jerry Seinfeld approached Lonstein, then a high school student, walking around in Central Park. After getting the then-17-year-old Lonstein's number, the pair started dating quite seriously despite the age difference (he was 39 at the time). Lonstein was a senior, and the two continued to date for the four years she attended college.

          Seinfeld spent a lot of time defending their relationship and the two split for good in 1997. Shortly thereafter, Seinfeld met his current wife, Jessica Sklar, who was a little more age appropriate. 

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