The 25 Club: Leo DiCaprio’s Dating History That’s Raised Eyebrows Over the Years

Leo DiCaprio has a lengthy yet niche resume when it comes to the ladies. The actor is famously known for dating Hollywood bombshells under 25 - from Bar Refaeli to Cami Morrone. Here's a look back at his famous flings...

Bridget Hall

During his many years on the market, the Once Upon A Time...In Hollywood charmer has gained quite the rep. It seems he's won over the most sought-after women in the biz - starting with Victoria's Secret models.

The first model that the actor reportedly linked up with back in 1994 was Victoria's Secret and Vogue cover model Bridget Hall - who was 17 at the time. However, the young and budding celeb was only three years older than Hall, and the relationship didn't last too long.

Naomi Campbell

Before he became a huge movie star, Leo allegedly had a fling with '90s supermodel Naomi Campbell. Although the 1995 romance was never confirmed or denied by either party, the kicker is she actually had a few years on him! That trend died very quickly, though…

Fast forward a few years, and the two actually have been spotted together - but just as friends! The paps have caught the two alleged exes with some mutual friends hanging out on vacations and attending each other's events. So safe to say, just friends.

Demi Moore

Well, the trend didn't die too quickly! Following DiCaprio's fling with the international supermodel, he allegedly cozied up with Demi Moore in 1997 right as the Ghost actress and her ex-husband Bruce Willis were mid-separation. So obviously, the rumor mill started spinning.

However, the allegations were never confirmed or denied by either party, but the "older women" trend still stood strong from his last fling. Moore is 12 years older than DiCaprio and actually soon became known for dating men noticeably younger than her, like ex-husband Ashton Kutcher.

Kristen Zang

Right as Romeo + Juliet premiered in 1996, Leo started dating model and actress Kristen Zang, following his models-only resume, who was one year older than DiCaprio. The duo dated for 15 months between 1996 and 1998, when the two were in their mid-twenties.

This was The Wolf of Wall Street's first lengthy public relationship before Kristen reportedly called it quit in 1998. According to The New York Daily News, a friend of the model claimed she was the "love of his life," and the reason they broke up was because Zang found him immature.

Helena Christensen

Leo and Christensen dated back in 1997, once again supporting the theory that the actor exclusively dates stunning supermodels. The famous pair were spotted together on several occasions at some of LA's top parties - around the same time Titanic was released.

However, neither party ever confirmed their fling with one another. Instead, the short fling further confirmed DiCaprio's pattern of dating Hollywood's biggest bombshells. And while she was 6 years older than him, he wouldn't continue dating cougars much longer…

Eva Herzigova

Another year, another supermodel. The year was 1998, and the young Leonardo DiCaprio had just released one of his most famous films to date, Titanic. And well, he was living large! So why not date the original Wonderbra bombshell, Eva Herzigova, to support his new stardom?

The two reportedly had a two-month fling after meeting at the premiere of The Man In The Iron Mask, but the Czech model denied all allegations. Why would anyone hide a fling with one of the biggest breakout stars? Well, rumor has it, Eva - who was 1 year older than Leo - was divorcing her husband at the time…

Gisele Bündchen

So sometime following his fling with Herzigova, by 1999, the Titanic star decided it was time to settle down. And who better to settle down with than Brazilian goddess Gisele Bündchen? Ah, the pattern continues. Not only was Leo dating the world's top model, but she was 18 when they started dating.

Leo was about 24 at the time, and once "Gionardo" made headlines, they were seemingly everywhere. Not only was she the only girlfriend of his to have accompanied him to the Oscars, but they had no problem sharing PDA. Unfortunately, things wouldn't end well for the happy couple.

Making Their Mark

However, before the big breakup went down, the two were deemed one of the hottest couples in Hollywood during their 5+ year relationship. From their unmistakably good looks to thriving careers and contagious personalities, they were basically 2000s royalty. And everyone knew it.

In 2004, just a few months before the break-up, the couple traveled to the Amazon Rainforest to meet the Xingui Indians to promote awareness about environmental issues affecting the area. So, not only were they a power couple in Hollywood, but they were using their powers for the greater good.

The Painful Truth

But behind closed doors, things were not as easy for the couple. And in 2005, they called it quits. In 2018, Bündchen released an autobiography, Lessons: My Path to a Meaningful Life, where she shared she went through a dark period in her early 20s, which eventually led to her decision to split with her now ex.

"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," she recalled. "Was I alone in wanting to do some serious soul-searching while he stayed the same? In the end, unfortunately, the answer was yes."

Bar Refaeli

Shortly after his relationship with Gisele came to a close, The Departed star began dating Israeli supermodel Bar Refaeli. Let the pattern continue: Leo and the Sports Illustrated model allegedly met at a party in Las Vegas back in 2005 or early 2006 and dated on and off for over 5 years.

As one might have guessed, the young model was around 20 when she met her soon-to-be beau - and Leo was around 11 years older than her. The couple was first spotted together back in 2006 during a romantic getaway in Paris. But from there, they kept their relationship pretty low-key...

"No One Needs To Know"

In an interview for La'Isha, an Israeli magazine, Rafaeli provided a little more insight into the reality of dating one of the biggest men in Hollywood and keeping their romance private. "I am there for him, and I am at all the events," she said, but "I just don't walk in hand-in-hand with him. I don't see any reason."

The model continued, "I don't see any reason. I don't need to strike poses with him in front of the cameras. No one needs to know how we kiss." Safe to say, the couple often kept to themselves, making only a few public debuts during their mysterious fling. As for when they did step out together?

Not The Average Date Night

However, one of their most notable and very public appearances was during a trip to Israel back in 2007, when the two were at their absolute peak. The couple went from sitting court-side at Lakers games to having a rather formal meeting with Israel's former Prime Minister, Shimon Peres.

DiCaprio's reputation as an activist, in addition to Bar being from Israel, led the two to meet with the former Prime Minister to promote environmental conservation and peace in the region. According to an inside source, the couple arrived casual - Leo even apologized to Peres for "not dressing properly."

Asking the Important Questions

Following their trip to Israel, People reported their romance had "ran its course," although the two were spotted traveling the world together throughout 2008. The couple went on another break for half a year in 2009, when Bar explained she "needed" the time apart to "understand a lot of things about myself."

"I worked on myself [and] I grew up," she told La'Isha. "I didn't know what 'alone' was like. Today I know that a relationship can work only if you know you can be alone and you are not afraid." The couple finally called it quits in 2011 - when the model was around 25.

Blake Lively

DiCaprio had a 5-month fling with one of Manhattan's it-girls, Blake Lively, following his on-and-off relationship with the Israeli model. The two publicly met for the first time in NYC back in 2010, when Lively was being considered to play Daisy Buchanan opposite Leo in The Great Gatsby.

Once Carey Mulligan scored the heavily sought-out role, rumors died down surrounding a potential relationship between Lively and Mr. Gatsby. However, things took a dramatic turn the following year when the two were spotted hugging on a yacht during the Cannes Film Festival. Were they an item?

A Childhood Crush

According to sources who were close to the couple, they had "never seen him like this with a girl," thinking this would be it for the long-standing bachelor. The couple was spotted exploring traveling the world together, from Monte Carlo to Portofino to NYC - and Blake was just about 24. Checks out, right?

The two seemed like they were on cloud nine, and in fact, Lively had her eyes set on Leo from an early age! In an interview with CosmoGIRL! a few years prior to the budding relationship, the Gossip Girl star told the outlet she "had a huge crush" on DiCaprio when she was a kid.

Goodbye, Mr. Gatsby

So, it looked like all that dreaming and wishing came to fruition during the lovebird's summer romance - but all good things must come to an end. Lively was nearing 25, summer was over, and the couple decided to call it quits after Lively visited DiCaprio in Australia, where he was filming Gatsby.

Following their split, an insider revealed to People that their breakup was "amicable," and one of the reasons they broke it off was due to Leonardo's "work commitments." Well, considering he was in the process of filming what would be one of his most successful films to date, perhaps we get it.

Erin Heatherton

Up next in Leo's lengthy dating history is Victoria's Secret Angel Erin Heatherton. That's right, everyone - another VS model, further pointing to the evidence that the man knows what he wants. Not to mention, she was around 23 years old when they briefly dated back in 2012.

The two were spotted together riding bikes through NYC that year and didn't last very long after that - but they appear to be on good terms. In an interview with Daily Mail Australia in 2015, she told the outlet, "He's a wonderful person, and he's a friend of mine," and that she wishes "him all the best."

Kat Torres

Another year, another model! The year's now 2013, and the pair allegedly began dating after meeting one another in Cannes. The Brazilian model opened up about their relationship to Extra, and the "amazing" Leo, back in October of 2013. But things didn't quite add up.

According to the reports, the 21-year-old model told Extra, "Leo is amazing, but I worry about what he will think about me talking to you. We have a pact that nothing can ever be said about our relationship." Well, that quickly raised alarm bells for fans. Shortly after, E! reported the two never dated - so the questions remain...

Toni Garrn

Following the alleged fling with Kat Torres, Leo was ready to return to his roots. That's right, a 22-year-old Victoria's Secret model. The actor began dating the German-born VS model back in 2013, and the couple lasted for about 18 months - one of Leo's longest relationships since Bar Rafaeli.

Two years following their public split, the couple were photographed together in the streets of NYC after enjoying dinner together, sparking buzz that their romance had rekindled. However, the rumors were just rumors, and the two claimed they were simply good friends.

Kelly Rohrbach

So, apparently, the key to this bachelor's heart might just be knowing how to ride a bike: in 2015, DiCaprio and then 25-year-old bombshell Kelly Rohrbach were spotted cycling alongside each other in Manhattan, showing each other a whole lotta love.

The model-turned-Baywatch actress and DiCaprio were reportedly even engaged at one point in the relationship. However, the rumored engagement was called off, and the couple broke up around New Year 2016. But soon, Leo would be moving on with a very famous billionaire...

Rihanna

Although their relationship was never confirmed, we are choosing to believe it true for all its worth - because wow. RiRi and Leo were rumored to have a short fling over the years, as they were frequently spotted together at the same parties and nights out. The two were even spotted in Paris together.

Our minds obviously began to race at the thought of the one and only Bad Gal getting cozy with Mr. Gatsby - and as it turned out, we weren't the only ones. One fan was even convinced the two are star-crossed lovers and is patiently waiting for the universe to manifest her wishes to reality. We'll just leave that one there.

Playboy Mansion After-Parties

The pair might just be friends - but the rumors and the pictures implied otherwise. Although RiRi just gave birth to a baby boy with A$AP Rocky, we can't help but wonder if the two ever did have a fling. Not to mention, they were reportedly spotted locking lips at a Playboy Mansion party following Leo's split from Rohrbach.

In addition to a potential make-out sesh at the mansion, Rihanna and DiCaprio were seen getting up close and personal during Coachella in 2016. And the rumors spread like wildfire. It was even rumored Leo snuck into the singer's birthday after-party in 2017. If only those walls could talk.

Nina Agdal

Following the RiRi rumors, Leo found his next love interest: a gorgeous blonde supermodel. Enter Nina Agdal. The actor was spotted with the 24-year-old bombshell at a club in Manhattan during the Summer of 2016. And well, the rest was history…

The two instantly hit it off, and they quickly became a globe-trotting couple. That same summer, the two were spotted getting cozy during a weekend in Montauk, but they were allegedly not dating at the time. However, Leo and the VS model were spotted vacationing in the Bahamas the next month.

Car Crash

The Sports Illustrated model and Leo quickly spent the rest of the summer traveling the world. The two were seen enjoying time at the beach in Malibu, partying on a yacht in Ibiza, and enjoying intimate time dating at NYC's hottest clubs and restaurants.

Amongst all the flirtation and fun, the two got into a car accident in the Hamptons, causing an ambulance to arrive at the scene. However, according to an inside source who spoke to People, the fender-bender wasn't serious, and the couple was "doing great."

2 Different Mindsets

The couple got more and more serious as months passed. A source even reported they were very much in love, and Nina was "like a breath of fresh air" for The Revenant star. The two spent the rest of the year traveling the world together, attending Golden Globe after-parties, birthdays, and more.

Although things looked great from the outside, it was time to call it quits for the pair the following summer. According to a source, it was Leo who broke things off as "He's not ready to settle down and just isn't in the mindset to get married or have kids." Or could it be that he reached his age limit?

Camila Morrone

Last but definitely not least: the Hollywood actor began dating actress and model Camila Morrone back in 2017 following his split from Nina Agdal. The Don't Look Up star and Morrone began dating when she was just 20 years old. Meanwhile, Leo was 42 - marking a 22-year age gap.

Apparently, though, the two go way back. Camila and Leo actually met through the model's former stepdad, Al Pacino, who introduced her to the actor when she was about 12 years old. And well, no one could predict what could possibly happen years later.

Love Is in the Air, Again

They were first spotted at the Cannes film festival (separately) back in May of 2017. But by the end of the year, the two were seen on various vacations, yachts, and shopping adventures. However, sources denied any romance between the two. Though, things became very clear when they showed up at Ellen DeGeneres's 40th birthday together.

The two traveled the world together - from attending the UEFA Champions League Group C football match in 2018 to celebrating life on a boat in Antibes, France. Things got very serious 8 months later when an insider reported he was "very in love" and even "talked about getting engaged."

Addressing the Haters

The couple always kept their relationship very lowkey and rarely made public appearances together - but they were very much in love. So when people began hating on the young model, criticizing the age gap between the two, Morrone finally addressed the situation.

The actress took to both her personal Instagram and an interview with the Los Angeles Times to explain that "anyone should be able to date who they want to date." She urged those to "live with a little less hatred and place their time and interests elsewhere" instead of on her.

The Final Strike

As the years went by, the two were pictured enjoying the U.S. Open in 2021, attending family functions, Hollywood parties, and more. And rumors had it they were "closer than ever" last year. Still, things were coming to a close shortly after the model's 25th birthday in June.

The couple was spotted enjoying the July 4th weekend together in Malibu, so news of their breakup last month came as a total surprise to all invested in their 5-year-long romance. However, there are currently no details regarding why the couple broke it off after so long. But spectators have an idea...

All Eyes on 25

Leonardo DiCaprio has one of the most unforgettable resumes in Hollywood - when it comes to both acting and dating. And as loyal fans pointed out online, the 47-year-old only seems to date women 25 and under. Coincidence? Calculated? The world may just never know...

One Reddit user even compiled a viral graph depicting a few of Leo's exes, their age when they started dating, their age when they stopped dating, and his age in comparison. The very well-organized graph shows a clear pattern: the actor's age limit has been 25. Will he ever break the cycle? It seems only time will tell.