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R. Kelly
- R. Kelly, as seen by 'Surviving R. Kelly,' has a slew of sexual misconduct allegations against him. Many might have forgotten before the release of the docuseries just how young Aaliyah was when she was dating the R&B singer.
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R. Kelly - The same year that she released ‘Age Ain’t Nothing but a Number,’ the couple married in secret. Aaliyah was 14, and R. Kelly was 27. The marriage was eventually annulled.
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Elvis Presley - The singer seemed to have a picture-perfect relationship with Priscilla Presley. However, the relationship started earlier than you might expect.
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Elvis Presley - Priscilla was just 14 when she met Elvis, who was 25. However, some claim that the relationship wasn't consummated until their marriage in 1967.
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Jerry Seinfeld - In 1993, Jerry Seinfeld was a star. His self-titled sitcom ruled TV, and there wasn’t too much controversy about his relationship with Shoshanna Lonstein.
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Jerry Seinfeld - Lonstein was a high schooler when Seinfeld first approached her, and had dated him since she was 17. He was 39 when they began dating.
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Kobe Bryant - Kobe and Vanessa Bryant have had a tumultuous relationship, which started when she was just 17 years old.
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Kobe Bryant - Kobe Bryant was 21 when he started dating the teenager, who he met on the set of a music video.
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Woody Allen - Woody Allen has had his fair share of headlines, both about his movies and off-set antics.
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Woody Allen - In 2018, The Hollywood Reporter claimed that Allen had an eight-year affair with Babi Christina Engelhardt, which began when she was 16.
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Taylor Swift - Taylor Swift has a burn book filled with celebrity exes, but her 2012 fling with Conor Kennedy may be her most controversial relationship.
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Taylor Swift - Kennedy, the great nephew of JFK, was 18 when he started dating Swift. The relationship didn’t last long, but there was a bit of backlash against 22-year-old Taylor.
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Luc Besson - Luc Besson is a pretty celebrated filmmaker, with a controversial past relationship with French actress Maïwenn. She first met the filmmaker when she was 12.
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Luc Besson - They started dating when she was 15, and Besson was 32. He fathered her child, who was born when she was 16. It’s said that Besson’s film, ‘Léon: The Professional,’ is inspired by his risqué relationship with Maïwenn.
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Wilmer Valderrama - Valderrama has a history with young women. He dated Mandy Moore when she was 16, and confirmed a relationship with Lindsay Lohan when she was 18, though many say they were dating before that.
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Wilmer Valderrama - Wilmer started to date Demi Lovato when she was 18, and the couple stayed together for nearly six years.
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Joel Madden - The pop punk rocker used to date Hilary Duff, who was younger than you might have remembered.
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Joel Madden - Madden started dating Duff when she was 16 and he was 25, but the relationship did not last.
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Tyga - Tyga raised eyebrows with his high-profile relationship with Kylie Jenner, who was 16 when she started dating the rapper.
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Tyga - The two didn’t last, and Kylie has moved on with baby daddy Travis Scott.
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The Weeknd - The Weeknd made headlines when he rekindled his relationship with Bella Hadid, who was quite young when she started dating the singer.
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The Weeknd - Hadid was 18 when she started dating Abel Tesfaye, who was 25.
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Nick Lachey - The actor and reality star was 25 when he started dating Jessica Simpson, who was 18.
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Nick Lachey - The couple found success with their reality series, ‘Newlyweds: Nick and Jessica,’ but broke things off in 2006.
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Chad Michael Murray - Murray made it big as an actor on ‘One Tree Hill,’ and started dating Kenzie Dalton when she was still in high school.
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Chad Michael Murray - Murray was 25 at the time, and they got engaged in April 2006. It didn’t last, and they went separate ways in 2013.
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Doug Hutchison - Doug Hutchison is perhaps best known for playing villainous roles. He also made headlines when dating Courtney Stodden.
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Doug Hutchison - Stodden was just 16 when she married Hutchison, who was 51. The couple wed in Las Vegas, after Stodden met him online. They divorced in 2019.
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Justin Gaston - The singer-songwriter started dating Miley Cyrus in 2008, when he was 20.
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Justin Gaston
- According to Popsugar, Cyrus was just 15 when she started dating Justin Gaston. The couple didn’t last, and they split up in 2009.
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Controversial celebs who dated teenagers
Celebs who rode the line of legality with their past lovers
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Age ain't nothing but a number, right? Celebs dating young stars is nothing new, but the preference seems to be all-the-more scandalous in the #MeToo era. Picturesque relationships like Elvis and Priscilla Presley, and The Weeknd and Bella Hadid, actually started earlier than you might think.
Take a look at celebs who dated teenagers at some point in their life.
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