“I’d be married by now”: Leonardo DiCaprio Hasn’t Found True Love Even After Dating Blake Lively and Many A-Listers

Even though Leonardo DiCaprio’s love life may look like a game of musical chairs—always shifting & changing—he knows how to keep us intrigued.

Leonardo DiCaprio’s love life really brings to mind that classic William Shakespeare line, “The course of true love never did run smooth” from A Midsummer Night’s Dream. 

It’s almost as if he has been living his own real-life romantic comedy, always on the lookout for that one person to settle down with, but somehow never quite finding the right fit.

With his good looks, globe-trotting lifestyle, and an endless parade of stunning women on his arm, you’d think he’d have found ‘the one’ by now.

But nope, the Titanic star seems to still be playing the field, searching for something deeper.

Leonardo DiCaprio in Shutter Island | Credit: Paramount Pictures.

From models with world-class walks to actresses who can steal the show, DiCaprio had more than his fair share of spectacular love interests.

But does he find ‘true love’, or is it just a game of musical chairs? Could the right person finally make him hit pause and settle down, or is he destined to keep moving forward in his ever-changing love saga?

The early dating years of Leonardo DiCaprio: Sweet, brief, and full of rumors

It all began in 1994 with Bridget Hall, the model whose brief link with Leonardo DiCaprio was nothing more than a blip in Hollywood gossip.

A year later, he was linked to Naomi Campbell, one of the most iconic models of the 90s.

We learned from Cosmopolitan.

Their relationship didn’t last long, but they’ve maintained a friendship since.

Relationships with models seemed to be DiCaprio’s go-to, making headlines all through the ‘90s, with names like Kristen Zang, Amber Valletta, and Eva Herzigová popping up here and there.

Though most of these were short-lived and filled with rumors in tabloid headlines, it seemed like DiCaprio was just getting started, the epitome of the heartthrob with a string of gorgeous ladies and no shortage of media attention.

Gisele Bündchen | Credits: Arezzo Brasil – YouTube | CCA 3.0/Wikimedia Commons.

Then came Gisele Bündchen, a relationship that stretched from 2000 to 2005 and looked like it might be the one.

But, as she later confessed, things weren’t meant to be.

DiCaprio’s inability to commit to the next step left the Brazilian beauty in search of a deeper connection. She wrote in her book:

No longer numbing myself with smoking, drinking, and too much work, I was becoming more and more aware of things that I’d chosen not to look at. 

Then came Blake Lively in 2011, a relationship full of potential but tragically short-lived.

A year and a half later, they broke things off, citing “distance” and “timing” as reasons (per E! News).

But let’s be honest, was timing ever the issue? Or was it more about DiCaprio’s constant search for something that seemed to always slip through his fingers?.

Blake Lively in It Ends with Us | Credits: SONY PICTURES ENTERTAINMENT INC.

The closest thing to a long-term connection came in 2017 when he dated Camila Morrone.

Their relationship seemed to be the one that truly made DiCaprio rethink his bachelor life.

According to the source (via People) he was “very in love and serious,” and the former couple had “talked about getting engaged.” .

Morrone, however, faced public criticism over their significant age difference, with her quiet and composed responses reflecting just how much she had to endure (per Vulture).

But in August 2022, things ended between the two (per E! News), and the internet couldn’t help but notice the all-too-familiar pattern—DiCaprio’s love life seemed to be more revolving door than a stable relationship.

Is Leonardo DiCaprio currently dating Vittoria Ceretti? Is it true love?

Leonardo DiCaprio in Inception | Credits: Warner Bros. Pictures.

And now, it seems that Leonardo DiCaprio has found himself once again intertwined with another beautiful model, Vittoria Ceretti, whom he met at the 2023 Cannes Film Festival (per ELLE).

A few months later, they were spotted on an ice cream date, their chemistry palpable enough to make insiders gush about how “exclusive” things have become between them (via Us Weekly).

He says she’s not only gorgeous, but super down-to-earth, and they have a ton in common.

She’s not intimidated by his fame at all—she even makes fun of it, ‘the model and the movie star.’ Leo finds it refreshing.

By November 2023, DiCaprio was reportedly “completely smitten” with Ceretti, claiming that “it’s going so well that Leo’s actually being exclusive.”.

But let’s not get ahead of ourselves.

While DiCaprio and Ceretti appear to be having a lot of fun together, it’s hard to ignore the trend: his romances always seem to be short-lived.

Ceretti might be the one that holds his attention the longest, but only time will tell if this relationship will break the pattern and give the actor the kind of love that lasts.

In an interview with The Sun, DiCaprio himself admitted,

My first love? Boy, I don’t even remember.

I suppose if I’d found my true love I would be married right now, wouldn’t I?

His words echo the complexity of a man who seems to have everything except the one thing he can’t seem to find: lasting love.

Maybe, just maybe, DiCaprio is still searching for that connection that’s more than just chemistry, excitement, and a few fun years together.

After all, in the end, it’s not about the number of beautiful women you date—it’s about finding the one who sticks.

Right?.