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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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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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Kobe Bryant -

Kobe and Vanessa Bryant had a tumultuous relationship, which started when she was just 17 years old.

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Kobe Bryant -

The late 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 since had two children with Travis Scott and is now dating Timothée Chalamet.

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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. Their on-and-off romance  lasted from 2015 until 2019.

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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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