Leonardo DiCaprio’s Dating History Shows The Actor Really Has A Type

Was supermodel Bridget Hall DiCaprio’s first girlfriend? We wouldn’t have thought so. Still, she was his first girlfriend whose face was famous from the most prominent catwalks. They were identified as a couple in 1994 and broke up in 1998. It isn’t known why the split happened. Both were entering the 20s, so maybe we should chalk this one up to young love.

A while later, DiCaprio took one of his first major roles as one half of Romeo + Juliet. Baz Luhrmann, of Elvis fame, directed him opposite rising talent Claire Danes. Did the sizzling connection work offscreen as well as on? Some say it did. Others say it didn’t. As in it really didn’t. He was 21, and she was 17. Either way, a classic movie was made.

Unconfirmed reports state that DiCaprio briefly dated iconic model and businesswoman Naomi Campbell during the 1990s. There’s an age gap of a few years, but who cares when you’re both this good-looking? One thing’s for sure: they’re definitely friends. Elle magazine refers to the surprising moment this serious actor did a photobomb when Campbell posed with 50 Cent. Sounds like the pair had fun!

Maybe DiCaprio didn’t date Claire Danes after all, judging by this appearance at a Romeo + Juliet premiere with his girlfriend of the time, Kristen Zang. They reportedly dated for a few years in the '90s. Both were the same age. A model, actress, and businesswoman, Zang recently spoke up concerning recent and mocking media coverage of DiCaprio dating considerably younger women. 

Writing for People magazine, she highlights the fact that many people don’t know what they want in life till they get older. Zang praises DiCaprio, describing headlines concerning his latest relationship break-up — of which more later — as “ageist.” She states: “Maybe she really cared for him but was just ready for the next chapter, perhaps it's temporary, or maybe it's none of our business.”

A gap of approximately 12 years — albeit in the opposite direction — exists between DiCaprio and another rumored girlfriend, Demi Moore. Speculation was fueled by a sighting of the pair in 1997. Both were part of a new wave of Hollywood stars, albeit in different decades. Moore famously started out as a member of the so-called “Brat Pack,” and DiCaprio rose up the ranks with the likes of Mark Wahlberg.

Model and actress Amber Valletta was another name linked to the heartthrob. As attractive people of around the same age, they may well have stepped out, though nothing has been confirmed. The story behind their rumored romance is a typical movie-star one — DiCaprio saw her picture and got in touch through their reps. It’s worked for acting colleagues such as Michael Caine!

DiCaprio’s Inception co-star Caine met his long-term partner Shakira after seeing her in an advertisement. So, while it seems like a standard A-lister thing to do, it can result in a healthy relationship. DiCaprio doesn’t need to go out and search for partners of course: we’re sure an orderly queue has been forming for a good couple of decades now. 

Supermodel and actress Eva Herzigová became a global star around the same time as DiCaprio. He was acting in movies such as What’s Eating Gilbert Grape? and she was saying “Hello boys!” as part of the traffic-stopping Wonderbra campaign. After reportedly crossing paths at the premiere for 1998’s Man In The Iron Mask, they apparently dated for a couple of months.

Between 1999 and 2005 DiCaprio was in a relationship with supermodel Gisele Bündchen. This appears to be the first confirmed case of the actor dating someone years younger than himself. Still, they did stay together for a while, and it seemed like they had a happy and productive relationship. What was the secret behind their enduring bond? For starters, they cared about the planet.

The couple shared a burning passion for environmental activism: they weren’t just seen together on the catwalk. In 2004 DiCaprio and Bündchen went to the Amazon rainforest, meeting the local Xingu Indians. Using their image to promote a healthy environment and warn about the dangers of pollution was clearly an important interest, one which they’ve continued following their breakup.

In 2016 DiCaprio co-produced and narrated the climate-change documentary Before The Flood to acclaim. In more recent news, Bündchen is reportedly gearing up to make a travel series in her native Brazil, with an emphasis on ecosystems. The pair seemed perfect together, arriving at the Oscars and showing off their super-glamorous side. So what ultimately ended the relationship?

Elle mentions Bündchen’s 2018 book, Lessons: My Path to a Meaningful Life, in which she refers to the conclusion of her romance with DiCaprio. Apparently, a desire to reconnect with herself and the ditching of habits such as smoking and drinking meant she would take a different path to her beau. It’s a shame but that’s the way things go sometimes, showing celebs are as vulnerable as anyone else.

These days DiCaprio is associated with younger models. Having broken up with Gisele Bündchen, he then became involved with another high-profile beauty, Bar Refaeli. There’s an age-ap of over a decade between them. They met when she was 20 and he was in his 30s. Their relationship, reportedly on and off, lasted till 2010. How serious did things get here?

DiCaprio and Refaeli met at a U2 concert and spent time getting to know each other after rocking out. He later visited her home state of Israel and met Refaeli’s mother in Tel Aviv, according to OK magazine. It’s said that they had a similar attitude to things, in that both were too caught up in stuff to ultimately settle down. 

It hasn’t been non-stop supermodels for DiCaprio of course. There was his reported romance of several months with Blake Lively in 2011. Lively is known for her acting in such movies as 2016’s The Shallows and 2018’s A Simple Favor. An age gap of about 13 years existed here, but they certainly shared a connection both in an acting and romantic sense. 

The relationship apparently happened when Lively starred in the original Gossip Girl, a TV show which ran from 2007 to 2012. Their interactions included globe-spanning dates and the perhaps obligatory sighting on a yacht in an exotic location — in this case, Cannes. Vanity Fair reported comments made by Gossip Girl producer Joshua Safran, who mentioned Lively communicating with DiCaprio via pictures of a doll. Now that sounds a little different!  

It wasn’t some voodoo ceremony: Lively was simply sending pictures of the toy to DiCaprio, presumably as some kind of in-joke. Who knows? What is clear is that Lively has been in a happy relationship with Deadpool star Ryan Reynolds for years. They met while filming a less-successful superhero picture, Green Lantern, in 2011: the same year she had a relationship with DiCaprio.

Might DiCaprio topline his own superhero movie and maybe bag a girlfriend that way? Unlikely. In a recent Vogue magazine interview, Dune star Timothée Chalamet revealed that DiCaprio advised him to avoid making comic-book flicks. These and hard drugs, but that’s a whole other story! DiCaprio’s frequent collaborator and legendary director Martin Scorsese has also criticized such films in the past.

Scorsese directed DiCaprio in 2013’s The Wolf of Wall Street, where he co-starred with Margot Robbie in her breakthrough Hollywood role. It’s been speculated that the pair became more than colleagues, though the consensus seems to be that they’re just pals. They went on to make the award-winning epic Once Upon A Time In Hollywood with Quentin Tarantino in 2019.

Back in 2012, DiCaprio began seeing model Erin Heatherton. The relationship between the actor and the Victoria’s Secret “Angel” reportedly lasted ten months. Here the age difference is pretty noticeable — she was 22 at the same, while he was approaching 40. That said, this was clearly more than a fling and ended due to their busy schedules, according to a report in Us Weekly magazine. 

By now you can probably make a guess as to what type of lady DiCaprio dated next… yes, it’s another model. But was it Miranda Kerr? Some seem to think so, though anyone speculating that way is probably reaching somewhat. The connection was established thanks to a Daily Mail report saying they were having dinner in a group in Las Vegas.

The jury seems to be out on whether DiCaprio dated model Kat Torres or not. She stated they were involved in some way, though at the end of the day there apparently wasn’t a relationship. If there was, then DiCaprio would have been seeing someone close to 20 years his junior. This story comes from 2013, the same year he was allegedly seeing Miranda Kerr. 

Toni Garrn was DiCaprio's next girlfriend. The model and actress dated him for 18 months, with the relationship lasting till Christmas 2014. His love life was really put under the spotlight when news of their break-up emerged. “According to tabloids, she broke it off after Leo was spotted leaving a Miami nightclub with 20 women,” wrote OK.

It’s a tough life but someone has to live it! We’re going to assume this story is a case of premium-grade tittle-tattle. Either way, it didn’t entirely separate DiCaprio and Garrn, who were in each other’s company long after, probably as friends. There was another age gap of approximately two decades between them, though his next date was a little older.

A couple of years were shaved off when DiCaprio met model and actress Kelly Rohrbach. They apparently dated in 2015. Rohrbach shot to even greater fame when she took the role of C.J. Parker in the 2017 Baywatch movie. Taking over the iconic, life-preserving part made famous by Pamela Anderson, she acted alongside Dwayne Johnson, Zac Efron, and Alexandra Daddario.

There was only an age difference of about 14 years between DiCaprio and his next romantic interest — at least according to speculation — Rihanna. The chart-topping singer and acclaimed actor certainly make a handsome couple, though we aren’t at all confident they did any more than form a friendship. They do have a connection though, and not only in terms of their social lives.

All of the people we’ve mentioned here are at least well-known, so press attention of their love lives is sure to follow. Yet Rihanna is one of the few on the rundown who’s had her personal details raked over as often as DiCaprio’s. They may well have joked about it in the past. Or he may have been talking to her about acting.

In recent years Rihanna has branched out from making music to performing in movies. She featured in high-concept curios such as Valerian and the City of a Thousand Planets (2017) and starred in big Hollywood films such as Ocean’s 8 (2018). Relationship-wise, she has started a family with rapper A$AP Rocky, meaning any possible romance with DiCaprio is undoubtedly in the distance.

In 2016 DiCaprio met yet another model, this time Nina Agdal. She made a name for herself for her appearances in the world-famous publication Sports Illustrated Swimsuit Issue. It comes as no surprise to learn she was born in 1992, a little later than DiCaprio’s birth year of 1974. The relationship was reportedly going well, so why did it end?

Apparently, the pair both agreed it was time to call it quits, though there doesn’t appear to be a lot more information than that. Typically we’ve seen DiCaprio break up with someone due to being too busy, or having different priorities. However it happens, he obviously doesn’t have an overwhelming desire to settle down. Unless, that is, he’s been desperately searching and simply hasn’t found the one.

At the time of writing, Leonardo DiCaprio’s last serious girlfriend was Camila Morrone. What does she do for a living? Do you really have to ask? She is of course a model and actress, who was born in 1997. Some mischievous commentators have noted that this was the year of Titanic, the Hollywood epic that became one of the actor’s biggest box office hits.

DiCaprio and Morrone were reportedly together for half a decade before breaking up in late 2022. She was 20 when they met, he was 42. Morrone is also connected to further acting royalty in the formidable shape of stepfather Al Pacino. DiCaprio acted with him in Once Upon A Time In Hollywood. Sources state it was another amicable break-up. Still, it has led to some rather strange observations.

Could it really be that DiCaprio gets cold feet about his lovers once they reach the ripe old age of 25? Well, one Redditor went to the trouble of creating a chart that analyzed stats in relation to the veteran actor’s numerous partners. None of them are over their mid-20s it seems!

Ricky Gervais wasn’t shy of having some fun with DiCaprio during the Golden Globes in 2020. Referring to the lengthy running time of Once Upon A Time In Hollywood, Gervais quipped: “Leonardo DiCaprio attended the premiere and by the end, his date was too old for him.” There was some amusement at the remark, including from the subject himself who was in attendance!

It’s good to know that DiCaprio can have a laugh at his own expense. As for the theory that he drops his romantic partners at the age of 25, we surely can’t say. Morrone was certainly that age when the separation occurred. Will DiCaprio ever step out with someone who’s been on the planet the same amount of time as him?

He isn’t short of people who speak of him in glowing terms, Morrone included. She took to Instagram to remind commenters that they didn’t know the person they were griping about at all. She added a wish that “people learn to live with a little less hatred and place their time and interest elsewhere because living without hatred feels pretty good.”

Safe to say, she won’t be the last lady linked to DiCaprio. Already the rumor mill has worked overtime over a range of names. Maria Beregova and Gigi Hadid are two that have surfaced in recent days. If and when the actor chooses to tie the knot and settle down, it’ll be the end of an era in journalistic circles. 

Meanwhile, his impressive acting career continues apace. He no doubt wants people to focus on what he does in front of the camera rather than behind the scenes. You don’t need to draw up a chart to work out that his contribution to Hollywood and its history is assured. A strong actor with a range of great movies is surely everybody’s type.