End Of An Era? Is Leonardo DiCaprio Engaged? A Look Back At His Legendary Dating History

Vittoria Ceretti at the 2024 Vanity Fair Oscar Party

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Lifelong bachelor Leonardo DiCaprio and Italian model Vittoria Ceretti have triggered engagement rumors this week after she was seen wearing a never-before-seen ring on her left hand.

DiCaprio, 49, and Ceretti, 25, were out grabbing some food at Mexican restaurant Yuca’s in Los Angeles on Tuesday afternoon when the ring was spotted.

Leo was in his usual attire of a white t-shirt, shorts, a black Los Angeles Dodgers cap and face mask, while Ceretti, with her hair braided in pigtails, wore numerous silver chain necklaces, but it was the silver ring that got the rumor mill firing.

Page Six points out that while they can’t confirm it is an engagement ring, she “notably has not worn the piece of jewelry in any recent Instagram posts.”

So is that it? Is Leonardo DiCaprio going full George Clooney and finally going to tie the knot now that he’s closing in on 50 after a lifetime of being single?

If so, it was a hell of a run he had.

Leonardo DiCaprio has either dated or been linked to an astonishing number of beautiful women over the years.

• Kristen Zang (model)
Gisele Bundchen (model)
• Bar Refaeli (model)
Blake Lively (actress)
• Erin Heatherton (model)
• Toni Garrn (model)
• Kelly Rohrbach (model)
• Rihanna (singer)
Dakota Johnson (actress)
• Bryana Holly (model)
Nina Agdal (model)

• Camila Morrone (actress)
• Eva Herzigova (model)
• Kat Torres (model)
• Miranda Kerr (model)
• Anne Vyalitsyna (model)
• Amber Valletta (model)
• Helena Christensen (model)
Demi Moore (actress)
• Naomi Campbell (model)
• Bridget Hall (model)
Gigi Hadid (model)

• Claire Danes (actress)
• Liv Tyler (actress)
• Virginie LeDoyen (actress)
• Victoria Lamas (actress)
• Bijou Phillips (actress)
• Eden Polani (model)
• Georgia Fowler (model)
• Lorena Rae (model)

Phew! That is a dating history that will probably never, ever be topped. And those are just the ones we know about.

I think the man has more than earned a little bit of domesticity after all of that. Assuming that he’s actually engaged, that is. After all, George Clooney did wait until he was 53 before he got married and we never thought that would happen, so… perhaps, four more years?

UPDATE: He’s reportedly not engaged, and the beat goes on.

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Before settling down at BroBible, Douglas Charles, a graduate of the University of Iowa (Go Hawks), owned and operated a wide assortment of websites. He is also one of the few White Sox fans out there and thinks Michael Jordan is, hands down, the GOAT.