In an interview with Esquire, DiCaprio and Anderson talk about their life’s “biggest regrets,” and DiCaprio lists passing on the role of Dirk Diggler among his. DiCaprio, who at the time had already signed onto Titanic, had a scheduling conflict, but he did help his Basketball Diaries co-star, Mark Wahlberg, land the role. (DiCaprio and Anderson have a film coming out later this year, One Battle After Another, which is their first project together — hence the convo.)

Leonardo DiCaprio Says 'My Biggest Regret' Is Turning Down 'Boogie Nights' Offer 30 Years Ago https://t.co/YDNAt8SJ5w

— Variety (@Variety) August 13, 2025

Other topics of discussion were centered around DiCaprio’s history of dating younger women, to which he chalked up to him still being, “emotionally 32,” despite having turned 50 last year.

So that certainly doesn’t seem like something he regrets — no matter all the jokes about his dating preferences.