Leonardo DiCaprio has once again made Hollywood history, officially adding another name to his line of high-profile Oscars dates. This year, it’s Italian supermodel Vittoria Ceretti, who has captured the spotlight alongside the actor (though they forwent walking the red carpet together) for the first time at Hollywood’s biggest night.
DiCaprio, 51, and Ceretti, 27, are believed to have begun dating in August 2023, when they were first seen together in Santa Barbara, California. Since then, they’ve kept things relatively low-key (as is DiCaprio’s signature), only appearing together at a handful of events, making this Oscars outing their red carpet debut as a couple.
Ceretti, an icon of the runway who has walked for the likes of Versace, Dior, Celine, and Louis Vuitton, also addressed the media attention that comes with dating a mega‑star in an April 2025 Vogue France cover story. She explained how frustrating it can be to be labelled “someone’s girlfriend,” but said that love gives her the confidence to shrug off outside noise. As with so many of DiCaprio’s high-profile relationships, the public is left piecing together clues from scraps of information.
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From Gisele Bündchen to Toni Garrn, there are only a handful of supermodels, actresses, and fashion icons who have accompanied him to the awards night. The couple has skipped other major awards shows; DiCaprio attended the 2026 Golden Globes alone.
While DiCaprio still keeps much of his personal life under wraps, Ceretti proved she can hold her own on the red carpet, bringing runway poise and undeniable glamour to a time-honoured Oscars tradition. Here, we look back at some of DiCaprio’s Oscar dates throughout the years.
Leonardo DiCaprio and date in the nineties
(Image credit: Jim Smeal/Ron Galella Collection via Getty Images)
Leonardo DiCaprio, who was nominated for Best Actor for his role in “The Aviator,” with then-girlfriend Brazilian model Gisele Bundchen at the 77th Annual Academy Awards in 2005 in Hollywood, California.
(Image credit: Vince Bucci/Getty Images)
Bar Refaeli, then girlfriend of Leonardo DiCaprio, poses solo on the red carpet at Cannes in 2007.
(Image credit: FRANCOIS GUILLOT/AFP via Getty Images)
In 2020, Leonardo DiCaprio took then-girlfriend Camila Morrone to the 92nd Oscars
(Image credit: ARTURO HOLMES via Getty Images)
Vittoria Ceretti, pictured at the 2025 LACMA Art+Film Gala at Los Angeles County Museum in 2025, attended this year’s Academy Awards with Leonardo DiCaprio.
(Image credit: Taylor Hill/FilmMagic via Getty Images)
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