Leonardo DiCaprio’s 49th birthday was on Saturday and he celebrated with a big party because, well, partying is what Leo does. Partying and modelising are Leo’s lifelong priorities which I guess is kind of impressive, in a weird way. 


When you’ve been partying for as long as Leo has, when you have basically been to the best parties in the world over the last 30 years, partying might lose its appeal, for some. But not for Leo, never for Leo. He seems as excited about the party on a random Tuesday as he is about the weekend party on his birthday – even though, for the most part, it’s the same people and the same sh-t. And by the same people, I mean that the models remain the same age. While he approaches 50. 

I wonder if he’s having a hard time with this. I wonder if he even acknowledges it. You know how Mariah Carey doesn’t acknowledge her age? Mimi says she is “eternally 12” and, well, Leo might just be the same, we just don’t talk about aging with men the way we talk about it with women. And society doesn’t look down on men who refuse to age the way we judge women for fighting it. But… like…it’s the same, isn’t it? Isn’t Leonardo DiCaprio also “eternally 12”? Next time he’s interviewed I hope someone asks him. Hey, Leo, HOW DOES IT FEEL TO BE ALMOST 50? 


Leo’s model of the moment is Vittoria Ceretti and there’s been reporting from the party that they were kissing all night. Just in time for cuffing season, we can call it now, I think – Leo is model-cuffed again. 

The other gossip coming out of Leo’s birthday is much less solid. Olivia Wilde and Chris Rock were there and they were photographed leaving together in the same car, and now there’s speculation, since they’re both single, that they might be a new thing. Olivia’s last relationship, of course, was with Harry Styles. And Chris and Lake Bell were together for a year or so but seemed to have called it off earlier this year. 

So is it Olivia and Chris now because the tabloids seem to be angling there? But maybe they don’t know that Chris dated Olivia’s best friend, Megalyn Echikunwoke, for four years. He and Megalyn broke up in 2020 and Olivia and Megalyn have been close since Olivia started in the business. 


Here they are at the Vanity Fair Oscar party just this year: 

Megalyn Echikunwoke and Olivia Wilde attend the 2023 Vanity Fair Oscar Party Hosted By Radhika Jones at Wallis Annenberg Center for the Performing Arts on March 12, 2023 in Beverly Hills, California

My point is, if Olivia’s BFF was with Chris for four years, it’s not a total stretch to think that she and Chris know each other well. And that they’ve remained friendly. Just an FYI before the rumours get louder. Based on a shared car ride? In this case it’s probably not enough to go on. 

Also attached – a selection of photos of some of the celebrities celebrating Leo’s pre-50 birthday. You can see a full list of who attended here