celebrities 17 Older Celebrities Who Actually Dated Teenagers  

Elle Tharp
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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 boyfriend and girlfriends 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. You have to stay young somehow.


Elvis Presley is listed (or ranked) 1 on the list 17 Older Celebrities Who Actually Dated Teenagers
Photo: Wikimedia

Who He Dated: Priscilla Presley, 14

Priscilla Presley, now 71, was only 14 when she met 25-year-old Presley at a party in Nauheim, Germany. She was the daughter of a U.S. Naval pilot, and Presley was serving in the army despite being a well-known musician. Presley'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 didn't sleep together until their wedding night. They had one daughter, Lisa Marie, and amicably divorced in 1973.

Profession: Soldier, Musician, Actor, Singer

Born: 1935-01-08

Credits: Love Me Tender, Blue Hawaii, Jailhouse Rock, Viva Las Vegas

Also Ranked

#8 on The Greatest Musical Artists of All Time

#3 on The Best Rock Vocalists

#4 on The Best Singers of All Time

#63 on Musicians Who Belong in the Rock and Roll Hall of Fame

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R. Kelly is listed (or ranked) 2 on the list 17 Older Celebrities Who Actually Dated Teenagers
Photo: Youtube

Who He Dated: Aaliyah, 15

R. Kelly has certainly gotten into a lot of trouble for his 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. Oh, the irony. 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. 

Profession: Film Score Composer, Record producer, Songwriter, Musician, Film Producer, + more

Born: 1967-01-08

Credits: Life, Sparkle, Fade to Black, Trapped in the Closet: Chapters 1-12, Trapped in the Closet: Chapters 13-22, + more

Also Ranked

#44 on The Greatest R&B Artists and Bands of All Time

#7 on Celebrities Who Would Probably Be Bad at Cuddling

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Taylor Swift is listed (or ranked) 3 on the list 17 Older Celebrities Who Actually Dated Teenagers
Photo: Youtube

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 long-distance, or because Swift obsessively stalked the Kennedy clan, depending on which source you believe. 

Profession: Guitarist, Musician, Singer-songwriter, Film Producer, Actor

Born: 1989-12-13

Credits: The Hunger Games, San Andreas, Valentine's Day, Hannah Montana: The Movie

Also Ranked

#87 on The Most Trustworthy Celebrities in the World

#66 on The Top Country Artists of All Time

#4 on The Best Current Female Singers

#39 on Famous Women You'd Want to Have a Beer With

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Jerry Seinfeld is listed (or ranked) 4 on the list 17 Older Celebrities Who Actually Dated Teenagers
Photo: People via Gawker

Who He Dated: Shoshanna Lonstein, 17

At the height of his Seinfeld fame in 1993, Jerry Seinfeld literally picked up 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 before he met his current wife, Jessica Sklar, who was a little more age appropriate. 

Profession: Television producer, Film Producer, Screenwriter, Actor, Voice acting, + more

Born: 1954-04-29

Credits: Seinfeld, Jerry Seinfeld: 'I'm Telling You for the Last Time', Comedian, Bee Movie

Also Ranked

#17 on The Funniest People of All Time

#5 on Celebrities Whose Lives You Want

#9 on The Funniest Stand Up Comedians of All Time

#30 on The Best TV Actors of All Time

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