Leonardo DiCaprio, the eternal bachelor of Hollywood, has long been teased for his habit of dating models under 25. But at 50, he’s flipping the script with 27-year-old Italian supermodel Vittoria Ceretti. Their relationship, now going strong for over two years, has fans buzzing is this the end of Leo’s infamous “under-25 rule,” or just another chapter in his playbook?
The Backstory on DiCaprio’s Dating Pattern
For years, DiCaprio’s romantic life has followed a predictable rhythm. He dated Gisele Bündchen until she hit 25 in 2005, Bar Refaeli until her 25th in 2011, and Camila Morrone right up to her 25th birthday in 2022. Critics call it immature, blaming his Hollywood roots and a taste for youthful vibes, but it’s sparked endless memes and debates.
Enter Vittoria Ceretti, born June 15, 1998, who’s already 27. She’s no newcomer to the spotlight, rising through campaigns for Versace and Chanel, she dated DJ Matteo Milleri from 2017 to 2020 before crossing paths with DiCaprio. Their 23-year age gap hasn’t gone unnoticed, but insiders say her independence sets her apart; she’s a successful model in her own right, not just arm candy.
How It All Started: A Timeline of Their Romance
Rumors kicked off in July 2023 with a cozy sighting in Santa Barbara. Things stayed casual through 2024, with occasional spots here and there. By early 2025, it turned serious, evolving from flings to something real.
Ceretti turned 26 in June 2024, marking the initial break from DiCaprio’s pattern, and they made their public debut at the Met Gala in May 2025. Fast forward to today: she’s now 27, and their low-key vibe includes joint vacations and events. In July 2025, magazines highlighted her independent streak in shoots, while the couple kept things steady.
Recent highlights? On August 18, 2025, they shared kisses and PDA on a yacht near Formentera, Spain, with sources calling it “serious and going strong.” Just days earlier, on August 14, DiCaprio hinted at settling down during a Venice event linked to Jeff Bezos’ wedding, mentioning lifestyle changes that scream commitment.
Latest Sightings and What They Mean
The buzz hasn’t slowed. On September 6, 2025, they hit an Oasis concert in Pasadena with friends like Jennifer Meyer, looking relaxed and coupled up. Then, on September 9, Ceretti showed up at the Los Angeles premiere of DiCaprio’s film One Battle After Another, cheering from the audience without hitting the red carpet later, they partied in LA.
These moments fuel the “maturing Leo” narrative, especially around his 50th birthday and career push. It’s a shift from his serial dating days, contrasting those past breakups. As one insider put it, “He’s finally ready to settle down… making changes in his life.”
Public Reactions: From Memes to Support
Social media’s take? A mix of satire and cheers. Viral Reddit headlines like “Leonardo DiCaprio ENDS HIS UNDER-25 DATING RULE WITH NOW 27-YEAR-OLD MODEL GIRLFRIEND” racked up upvotes in June 2025, echoing X posts joking about engagements post-26. One November 2024 X quip about “engagement after 26” got 8.9K likes, keeping the light-hearted mockery alive.
Not all positive, age-gap critics resurfaced with the yacht PDA and premiere, calling out “creepy” vibes from 2022-2024 memes. There’s also environmental hypocrisy shade, like a January 2025 X post on their private jet to Mexico, hitting 621 likes amid DiCaprio’s activism.
On the flip side, fans applaud Ceretti’s supportive premiere appearance, with X buzz calling it sweet. Viral moments include a September 2024 Milan video (1.6K likes) and a June 2025 Venice photo (283 likes). Overall, the chatter’s playful, with satirical takes adding levity—think X jokes about “donkey” looks or 2024 split rumors that fizzled.
Some see it as genuine growth, not a repeat pattern. As an ELLE piece noted in July 2025, “The relationship evolved into something serious that is still going strong.” And their chemistry? “Easy and unforced,” per insiders.
Controversies and Fresh Angles
No major scandals here, but the age difference keeps stirring pots. Yacht smooches and premiere spots reignited debates, blending with ongoing “creepy” memes. DiCaprio’s eco-activism clashing with jet-setting adds another layer, as seen in that viral X post.
Trending? The idea that Ceretti signals DiCaprio’s evolution, tied to his milestone birthday and films like One Battle After Another. It’s a unique spin: her career independence makes this feel different, like a real partnership. For more on stars breaking molds, check out these fascinating secrets about Tessa Thompson or interesting facts on Dolly Parton.
Is This the Real Deal for DiCaprio?
At the end of the day, DiCaprio and Ceretti’s story has us all watching. From casual starts to serious vibes, it’s breaking his old rules and sparking fresh talk. Whether it’s forever or just now, one thing’s clear: Leo’s keeping things intriguing, and fans can’t look away.
