Leonardo DiCaprio Accidentally Admits He's Insecure About His Affinity For Age-Gap Romances

First, Leonardo DiCaprio was infamously known as the Hollywood actor who still hadn't won an Oscar despite being nominated multiple times and giving phenomenal performances. Then, after he won his first (and only) Academy Award in 2016, chatter around him quickly shifted to his questionable dating life. He's notoriously known for dating much younger women, with countless memes joking about him breaking up with partners once they reach 25. Even pop star Sabrina Carpenter's 25th birthday cake poked fun at DiCaprio's affinity for younger partners.

The activist is constantly trolled for his age-gap romances, including when Ricky Gervais roasted DiCaprio at the 2020 Golden Globes. It was a big deal when he casually dated Gigi Hadid in 2022, since she was 28, well past DiCaprio's age threshold. He's currently dating 27-year-old Vittoria Ceretti, with rumors that he's finally settling down. But in a new interview for Esquire, done by filmmaker Paul Thomas Anderson, who directed DiCaprio in the upcoming movie, "One Battle After Another," the former child actor provided insight into why he always goes for younger women.

When Anderson asked DiCaprio to share how old he thought he was if he didn't actually know, he answered 32. (He's actually 50 at the time of writing.) Later, he joked that he's emotionally 35. Reflecting on his milestone birthday, DiCaprio explained, "It creates a feeling like you have a desire to just be more honest and not waste your time. I can only imagine how the next few decades are going to progress."

If Leonardo DiCaprio really does think of himself as a 32-year-old trapped in a 50-year-old's body, then this would partly explain why he goes for women in their early 20s. Granted, dating a 21-year-old when you're 32 is still a big difference, but it at least makes a tad more sense than being half a century old and wanting to date an early twentysomething.

DiCaprio reportedly refuses to date women over 25, but he's at least being upfront about that. In the Esquire interview, the "Inception" actor offered more insight into his decision-making process. "Being more upfront and risking having things fall apart or risk the disagreements or risk going your separate ways from any type of relationship in life — the personal, professional — it's that you just don't want to waste your time anymore," he shared, noting how the first half of his life is over. He may not make it another 50 years, so he wants to make sure every moment counts, because his time feels more finite at his age than it would to a twentysomething.

Of course, this conscious dating decision hasn't helped boost his reputation, which took a nosedive during Wimbledon 2025. The official Wimbledon account on X, formerly known as Twitter, made a "Titanic" pun and shared a photo of DiCaprio enjoying the tournament. The comment section was on fire, with people trashing him over numerous things, including his dating life.