But, really, did Leonardo DiCaprio ever leave the party beat? It’s probably not all that accurate to say he’s “back” on the party beat because whether he’s in a relationship or not, Leo’s always at the party – it’s just that, now, he’s single at the party for the first time in almost five years. 


Which is why I was surprised not to see him at the US Open last night because so many celebrities have been at the US Open this week to see Serena play – and Leo, reliably, wants to be where everyone else is. Maybe he was there and the cameras just didn’t catch him? Or maybe he’s planning to show up later in the week, perhaps tonight when Venus and Serena play their first doubles match? Or tomorrow for Serena’s third round match? It’s Friday night after all. Something to do before he hits the club. 

Which, according to Page Six is what he’s been doing this week, checking out the new clubs in New York with his crew and a “squad” of models aged 21-23. Page Six’s sources also say that

“By the time girls reach 25, they’re looking for more — they’re looking to get married and settle down. That is not what Leo wants. He does not want a family and does not want to be around women who may press him for that. The minute a girl meets him, the clock is ticking. If she gets too old, in a couple of years, she is gone. If she gets too close, in a couple of years, she is gone. He’s gotten older but his taste has not gotten any older.”

Curious to know who these sources are because anyone deep inside Leo’s inner circle wouldn’t be putting him on blast. Hilariously though, one of the people quoted in Page Six’s story about Leo and Camila Morrone’s breakup is Heidi Fleiss, known as the “Hollywood madam” who has spent time with Leo and his people over the years. Heidi defends Leo: 

“Good for him. I’m on his side,” Fleiss told The Post. “He connects with women who are young and beautiful. He wants people who stimulate him mentally and physically. Why does he need to be with some woman who’s been through the wringer, who’s desperate to get what she can out of him and wants to tie him down?

“There’s something to be said for going out with people who are happy with themselves and excited about life — who can turn you on to new things and ideas that you may not already know about.”


For those of you who may not have been around back in the day, the Heidi Fleiss story is one of the biggest scandals in Hollywood history. She was accused of running a high-class sex work business (commonly referred to as a “prostitution ring” but I’m not sure if that term is acceptable anymore and if you have thoughts about alternatives, please let me know) making money from wealthy and famous clients. Everyone wanted to know, for years, who was in her “Black Book”. 

Given Leo’s reputation for partying exclusively with models, like wall-to-wall models all the time, and his reputation for dating models who are 25 years old and younger, and the stories about him placing orders for models wherever he parties, and how increasingly squicky this has become over the years, um, does Leo really want Heidi Fleiss of all people to be PR-ing his breakup and romantic preferences? 

By the way, that article I just linked to at Vulture is from 2014, recapping decades of Leo’s models + party history. Including the time that year when he partied with Joe Jonas and then left a club with 20 models, inspiring this envious reaction by a witness who saw it all go down: 

“He left with 20 girls. Leo and 20 girls. He is my hero. He was overflowing with models everywhere. The Jonas brother looked scared, like he was going to drown and suffocate in the women. His face was hilarious.”


Leo was then 40 years old. He will turn 48 years old in November. And… well… by the sounds of it, at least according to Page Six and Heidi Fleiss, he is still about that life. 

That said, there are a few people who have messaged me wondering if we’re reading the data wrong. This, by the way, is the data – and yes, it needs to be updated with the Camila breakup: 

Leonardo DiCaprio Refuses To Date A Woman Over 25 graph


The people who have messaged are asking whether or not it’s possible that it’s Leo’s exes who are doing the dumping when they turn 25 and not the other way around. If we’re going by his last five girlfriends, did Erin Heatherton, Toni Garrn, Kelly Rohrbach, Nina Agdal, and finally Camila Morrone all wake up after they turned 25 and realise that they were done with this perpetual man-child? 


Can it be a combination of both? In the months leading up to their 25th birthdays, does Leo start pulling away and dropping hints? Is he inattentive and insensitive? Does he lean over mid-way through dinner or during a bike ride to remind her that he will never want to get married and have children but is having such a beautiful time with her? Does he make it so that she has no choice but to come to accept that there is no future here and when the clock strikes 25, she comes to terms with it and bounces? 

Or are they the ones who peace out suddenly leaving him with an outstretched arm, staring at closed door, wimpering “please don’t go”? 

Either way, whether or not he’s allergic to women maturing or refusing to mature to the point that women mature beyond him, it all still comes back to his pattern of dating models fresh out of their teens and no longer dating them anymore as they progress into adulthood. It’s… not a good look?!

Attached - Leo out in Malibu earlier this week before arriving in NYC.