Leonardo DiCaprio's Most High-Profile Failed Relationships

Leonard DiCaprio's dating history makes it abundantly clear that he has a type. The "Titanic" star has primarily been in relationships with models who are considerably younger than him (generally falling under the age of 25). It certainly seems like the Oscar winner is strict on the age of his partners, as DiCaprio notoriously broke up with several women right after they reached their mid-twenties. Speaking to the New York Post, a confidant offered some insight into the actor's supposed reasoning: "By the time girls reach 25, they're looking for more — they're looking to get married and settle down." The source continued, "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." 

Likewise, Dicaprio also tends to bolt from romantic relationships once a partner starts to know and understand him a bit too well. However, there was a time when the "Inception" star wasn't completely against the idea of a long-term commitment. In a 2010 chat with Germany's OK magazine, the A-lister shared that he could actually see himself having children in the future. 

However, DiCaprio couldn't realistically consider the possibility because of his packed schedule. The actor also candidly confessed that he was often plagued by loneliness because his career isolated him from his loved ones. Still, DiCaprio didn't let it affect him too much as he rationalized, "I generally concentrate on work and push any feelings of yearning away," (via Digital Spy).

Gisele Bündchen and Leonardo DiCaprio are just one of the many couples from the early 2000s that you probably forgot even dated. In an interview with Entertainment Tonight in April 2000, the Victoria's Secret Angel recalled that she became friends with the "Romeo + Juliet" star a few months prior. Although their connection turned romantic shortly afterwards, critics believed the relationship was purely for show. But the model scoffed at the doubters in a September 2000 Rolling Stone chat, pointing out that they both had thriving careers well before they got together. 

Then, while speaking to W magazine in November 2002, the supermodel seemingly confirmed that her romance with DiCaprio was over by confessing she was simply too busy to commit properly. However, in June 2003, an insider told the San Francisco Gate that the power couple had rekindled their relationship and were looking to lock things down shortly. Likewise, in 2004, People reported that the Oscar winner was trying to get his hands on a custom Neil Lane diamond ring. 

However, the couple broke up for good shortly after attending the 2005 Oscars together. In her 2018 memoir "Lessons: My Path to a Meaningful Life," Bündchen explained that after she stopped using unhealthy coping mechanisms, she gained more clarity about their relationship and realized they were no longer compatible, writing, "Was I alone in wanting to do some serious soul-searching while he stayed the same? In the end, unfortunately, the answer was yes," (via USA Today).

Shortly after Blake Lively's 3-year relationship with her "Gossip Girl" co-star Penn Badgley ended, she was spotted enjoying a cozy dinner with Leonardo DiCaprio, in November 2010. However, E! News clarified that it wasn't all that romantic since the duo was joined by a whole group of people, including director Baz Luhrmann. Lainey Gossip reported that the "Rhythm Section" star had done a screen test with the Oscar-winning actor for the part of Daisy Buchanan in Luhrmann's "The Great Gatsby." Unfortunately, they didn't click on screen, and the iconic role ended up going to Carey Mulligan instead. 

Nonetheless, DiCaprio and Lively's offscreen chemistry appeared to be pretty strong when they were photographed in Cannes in May 2011. In the months that followed, the A-listers embarked on several fun little dates all over the globe. Although they seemed to be going steady, E! News confirmed that Lively and DiCaprio had broken up in October 2011. An insider divulged to the publication that the busy actors simply couldn't keep up with being long-distance anymore. 

Still, it all worked out for Lively because she started dating Ryan Reynolds later that same month. While she and DiCaprio remained tight-lipped about their romance, "Gossip Girl" executive producer Joshua Safran did share an odd detail about it when he spoke to Vanity Fair in 2017. "When I think about shooting the L.A. episodes, Blake was dating [DiCaprio] at the time, and she had this thing where she had a doll that she took photos of that she sent to Leo," he revealed.

According to W magazine, Camilla Morrone's stepfather, Al Pacino, introduced her to Leonardo DiCaprio when she was around 12 years old. Nearly a decade later, in December 2017, the "Don't Look Up" star was spotted walking out of the model's home. In the following months, the celebrity couple continued to make unofficial public appearances together. Their relationship was apparently getting serious in July 2018, as Just Jared reported that they had hung out with Morrone's mother on a yacht. A month later, a source even suggested to Us Weekly that DiCaprio may have finally found The One, enthusing, "They're very in love." The insider even added, "They've talked about getting engaged," noting that the actor hadn't ever felt like this before. However, their romance wasn't exactly well-received because the "Daisy Jones & The Six" star was 23 years her beau's junior. 

Morrone addressed the backlash directly in a 2019 interview with the Los Angeles Times, arguing, "There's so many relationships in Hollywood — and in the history of the world — where people have large age gaps." She continued, "I just think anyone should be able to date who they want to date." Although everything seemed to be working in the couple's favor, the big 2-5 crept up, and People confirmed their breakup in August 2022, a mere two months after Morrone celebrated her birthday. In the aftermath, a source disclosed to E! News that DiCaprio and Morrone's romance died out because their careers took them away from each other too often.

Shortly after Leonardo DiCaprio and Camila Morrone called it quits, he was spotted strolling round New York with fellow model Gigi Hadid. Later, a source told People that they had known each other for quite some time since the unlikely duo had loads of mutual friends and hung out at similar spots. However, although they were enjoying each other's company, DiCaprio and Gigi hadn't officially started dating because he wanted to process the end of his lengthy relationship with Morrone first. Their relationship had caught speed by November 2022 as an insider informed Entertainment Tonight that Gigi's mother, Yolanda Hadid, and her sister, Bella Hadid, were stoked about it. Then, in February 2023, another insider told People that their high-profile romance had "fizzled" because the duo had vastly different priorities. The confidant further noted that things had remained pretty casual throughout. 

About a month later, a source disclosed to People that the Victoria's Secret model and "The Revenant" star had spent almost the entirety of a pre-Oscars party in each other's company. Meanwhile, another onlooker claimed that they were amongst their friend groups in the VIP section. After some back-and-forth, they both seemingly moved on from their association in September 2023. Gigi supposedly started dating Cole Bennett and DiCaprio started seeing Vittoria Ceretti. Later, a source confirmed with Us Weekly that their work-related travel had driven them apart and their priorities weren't aligned since Gigi wanted to turn her attention to raising her daughter.

Leonardo DiCaprio was once in a long-standing relationship with Israeli model Bar Refaeli. According to the New York Post, the "Killers Of The Flower Moon" star met 20-year-old Refaeli at a U2 party in 2005. They started dating at some point in the following year and were spotted enjoying several cutesy dates along the way. Though DiCaprio and Refaeli split up in 2009, their breakup only lasted about six months, with the celebrity couple reuniting in 2010. Speaking to Vogue in March of that year, the Sports Illustrated model shared that she bettered herself during their brief split. Rafaeli elaborated, "From a very young age I have always had a boyfriend and I didn't know what it was like to be inside my own skin. Today I know that a relationship can work only if you know you can be alone and you are not afraid. Now I'm not afraid of being alone." 

Unfortunately, they ended up splitting up for a second and final time in 2011. Similar to DiCaprio's previous high-profile relationships with fellow celebs, this breakup, too, boiled down to incompatibly busy schedules and a lack of desire to lock things down, as a Daily Mail source subsequently detailed. A few years later, the Oscar winner got into a short relationship with another Sports Illustrated model, Kelly Rohrbach, and they reportedly ended things for the same reason. If DiCaprio's dating history wasn't glamorous enough, he also reportedly had a rumored fling with Rihanna in 2015.