Anything can happen at the 2025 Academy Awards, including worlds colliding and exes like Timothée Chalamet and Lily-Rose Depp potentially crossing paths.
Chalamet, 29, and Depp, 25, were thrust back into the same room on Sunday, March 2, while attending the Oscars at Los Angeles’ Dolby Theatre at Ovation Hollywood.
Chalamet arrived at the awards show in celebration of his nomination for Best Actor in a Leading Role for playing Bob Dylan in A Complete Unknown. The film is also nominated for the biggest award of the night: Best Picture.
Depp, meanwhile, was invited to Hollywood’s biggest night as a presenter. She wore a sheer black dress with lace detail while walking the red carpet prior to the event.
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As Chalamet got cozy at his seat with girlfriend Kylie Jenner, Depp dazzled on stage as part of the presenting team for Best Costume Design. Depp was joined by Elle Fanning, who is one of Chalamet’s A Complete Unknown castmates, John Lithgow, Connie Nielsen and Bowen Yang to give Wicked the award.
Former spouses Dennis Quaid and Meg Ryan were also spotted attending Hollywood’s biggest night. Quaid, 70, brought his wife, Laura Savoie, as his plus one, while Ryan, 63, walked the red carpet solo. (Quaid and Ryan divorced in 2001 after 10 years of marriage. They share son Jack Quaid.)
Emma Stone and ex-boyfriend Kieran Culkin were more evident about their Oscars reunion. In fact, an eyewitness told Us Weekly that Culkin, 42, and his wife, Jazz Charton, “came down and met Emma and gave her a huge hug and we’re so excited to see her.” The couple were spotted chatting with Stone — who produced A Real Pain, which earned Culkin his first Oscar win on Sunday — for a “few moments” before returning to their seats. (Stone, 36, and Culkin dated from 2010 to 2011.)
While Chalamet wasn’t seen publicly interacting with his ex at the awards show, fans still remember their whirlwind romance well. Us Weekly broke the news in October 2018 that the pair were dating after they were spotted kissing in New York City that same month.
The following year, the Call Me by Your Name actor and Depp made headlines once again after being photographed passionately kissing on a boat in Italy. The September 2019 makeout session went viral and haunted Chalamet for years.
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“I went to bed that night thinking that was one of the best days of my life. I was on this boat all day with someone I really loved, and closing my eyes, I was like, indisputably, ‘That was great,’” Chalamet told GQ in his November 2020 cover story. “And then waking up to all these pictures, and feeling embarrassed, and looking like a real nob? All pale? And then people are like: ‘This is a P.R. stunt.’ A P.R. stunt? Do you think I’d want to look like that in front of all of you?!”
Chalamet and Depp’s Italian vacation was their last public outing before they called it quits. Us confirmed in April 2020 that they parted ways after more than one year together.
Us confirmed in April 2023 that Chalamet was seeing Jenner. “He’s very charming and he makes her laugh, and he’s easy to talk to,” an insider said at the time, adding, “He’s not like any of the other guys she’s dated before and although he may not seem like her type, they have really good chemistry.”
Lily-Rose, meanwhile, confirmed her romance with 070 Shake (real name Danielle Balbuena) in May 2023. The twosome initially sparked relationship speculation when they were spotted at Paris Fashion Week together that February.
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Outside of running into his ex, the Oscars marked the end of a big awards season for Chalamet. The actor was previously nominated for his role in A Complete Unknown at the BAFTA Awards, Critics Choice Awards, Golden Globe Awards and many other smaller awards ceremonies.
He won Outstanding Performance by a Male Actor in a Leading Role for his portrayal of the iconic musician at the 2025 SAG Awards in February.
“I was not expecting this at all, truly. I know the classiest thing would be to downplay the effort that went into this role and how much this means to me, but the truth is this was five and a half years of my life,” Chalamet said during his February 23 acceptance speech. “I poured everything I had into playing this incomparable artist. Mr. Bob Dylan. A true American hero. It was the honor of a lifetime playing him.”
