9 Celebrities Who Have Dated Teens — Is Leo\'s New Girlfriend 19?
Leonardo DiCaprio movie roles
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9 Celebrities Who Have Dated Teens — Is Leo’s New Girlfriend 19?


Celeb guys often date much younger women, but some famous dudes have had girlfriends who are still in their teens.

It’s not as shocking when it’s a 20-something dating someone younger — but when the older lovebird is in his or her 30s, 40s, or 50s, we raise our eyebrows.

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Chelsey Weimar, a model whom Page Six says is Leo's new lady love, is either 19 or 20, based on two posts saying she was 15 in 2012, when she won Dutch reality show The Face.

With that in mind, here are some famous examples of celebs who have dated teenagers — some of whom had us looking up age-of-consent laws!

Henry Cavill, Tara King

The Man of Steel star brought his 19-year-old date, a student at Bristol University, to an Oscars after-party this weekend.

“People say, ‘Age is just a number,’” he told Elle UK. “A lot of times it’s not just a number. It’s actually a real and true sign of someone’s maturity. But in this case, she’s fantastic.”

(Henry, we can think of a lot of eligible 32-year-old bachelorettes. Pippa Middleton is single, right?)

The Weeknd, Bella Hadid

The “Can’t Feel My Face” singer started dating the model when he was 25 and she was 18.

Wilmer Valderrama, Demi Lovato

This ‘70s Show star started dating his Confident lady sometime in 2010, the year she turned 18 and he turned 30.

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Joel Madden, Hilary Duff

This Good Charlotte rocker started romancing the Disney Channel actress when he was 24 and she was 16.

Sam Taylor-Johnson, Aaron Taylor-Johnson

This Fifty Shades of Grey director fell in love with her now-husband, best known as the star of Kick-Ass, on a film set when she was 42 and he was 19.

Jerry Seinfeld, Shoshana Lonstein

The Seinfeld star was 38 when he started dating Shoshana, and she was either 17 or 18, depending on which report you believe.

Milo Ventimiglia, Hayden Panettiere

News of these Heroes co-stars’ hookup made headlines in December 2007, when he was 30 and she was 18.

Tyga, Kylie Jenner

After months of speculation around these tabloid targets, he confirmed their relationship in March 2015, when he was 25 and she was 17.

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Doug Hutchison, Courtney Stodden

In what may be the most shocking celebrity May-December relationship, this character actor married his on-again off-again wife when she was 16 and he was 50.