A Complete Timeline Of Leonardo DiCaprio's Relationships

Unless you are brand new to the internet and memes and what have you, you're certainly familiar with the lore surrounding Leonardo DiCaprio's love life — namely, that he seems to be allergic to dating anyone who is under 25. 

In August 2022, DiCaprio and his girlfriend of four years ended their relationship, and yes, she happened to be just over 25 years old at the time of their breakup (more on that later). Hot on the heels of that split, the rumor mill wasted no time churning out some fresh gossip: According to a number of reports, DiCaprio and supermodel Gigi Hadid have supposedly connected. As one source claimed to ET, "Gigi and Leo are the real deal." To make matters more interesting, Hadid is over 25. Maybe DiCaprio has changed?

Jokes about age aside, Hadid does indeed line up with the Oscar winner's "type." Over the years, DiCaprio's dated a lot of beautiful models and/or actors, so getting involved with the stunning runway stomper wouldn't exactly be out of character. DiCaprio's love life is the stuff of legend, so without further ado, let's get into the ups and downs of the Hollywood A-lister's rumored flings and confirmed relationships.

In 1994, rumor had it Leonardo DiCaprio and Bridget Hall were an item. Now, the two never said they were an item, but some outlets sure added fuel to the gossip fire. In 1998, for example, The London Sun (via the Calhoun Times) claimed Hall and DiCaprio were not only intimate, but that she'd lost her virginity to the actor. Oh, and DiCaprio supposedly, according to the outlet's source, "dumped her like a hot potato." Oh, and she supposedly called their time together "disappointing." Both Hall and DiCaprio's teams denied this story. It's also worth noting that when asked about DiCaprio, Hall told New York Magazine, "Nothing happened."

For Hall's part, she fell off the map in the early 2000s, deliberately taking a hiatus from the spotlight. However, since then she's crept back into the social landscape and told Dujour that she was ready to get cracking again. "The past three years, I've been in hiding, taking a break," she said. "Now I'm getting back into shape and getting to work again." What prompted this return? "I know I'm not getting any younger, so it's got to be now or never," Hall said. Oh dear. Could this spawn even more memes about DiCaprio's ageism?

Leonardo DiCaprio reportedly dated co-star Brittany Daniel briefly in 1994, according to The Sun. They met while filming 1995's "The Basketball Diaries." Brittany starred alongside her real life twin sister, Cynthia Daniel.

While her relationship with DiCaprio didn't last long, Brittany has remained a vital part of Hollywood thanks to films like "White Chicks" and TV shows like "Sweet Valley High." In 2011, as she was about to start filming "The Game," Brittany sought medical advice after noticing unusual symptoms, including back pain. She was diagnosed with IV non-Hodgkin's lymphoma, a form of cancer that targets the lymph nodes, according to Cancer Center.

"It happened so suddenly," Brittany told People, saying that she and her mother moved in with her twin sister while she went through treatment. "There is no way I would have ever gotten through this without my family," she added. "My family is everything to me and I feel like they saw me through this." She said she's committed to letting people know that they have a chance, even after such a serious diagnosis. "I am just trying to enjoy every day," she said. Sounds like any thoughts of her long-ago fling have flitted away.

Back in 1995, Leonardo DiCaprio was just beginning his trend of dating supermodels and apparently looked no further than '90s icon Naomi Campbell. The reported relationship wasn't a long one, but whatever it was ended up blossoming into a lifelong friendship. 

As recounted by Hello!, Campbell and DiCaprio were photographed hanging at Jason Statham's home in 2015. DiCaprio was acting as the party's DJ, and Campbell joined in on the music fun. Actor O'Neal McKnight told the outlet, "He and Naomi were having fun going back and forth for about an hour and a half playing songs." McKnight added that "The Revenant" star's choice in music was a huge hit with party guests.

The two friends were spotted again in 2022 in London for the wedding of British Vogue editor Edward Enninful and Alec Maxwellseen, according to the Daily Mail. Following the wedding, which took place at an estate in Wiltshire, some of the guests were spotted out and about together in London. According to the outlet's sources, DiCaprio apparently brought a boatload of roses to a restaurant and handed them out to a number of patrons, including Campbell. They may not be lovers, but clearly, things are amicable between the supermodel and actor.

Leonardo DiCaprio and actor Kristen Zang started dating in 1995, and as The Sun noted, she was his date to the "Romeo + Juliet" premiere. Their courtship lasted four years.

Interestingly, Zang reached out to People in September 2022 when news the news broke about his split from Camila Morrone, and Zang wanted to push back against the "agiest" label that's been assigned to DiCaprio. Using her own relationship with him as a watermark, Zang said she does not think of him as a serial dater who goes out of his way to date someone in their low 20s. "Leo was a very sweet and thoughtful boyfriend," she told People. "We also had some hard times like all couples do, and broke up for a bit in 1997 and then got back together. Then, about 4 months after my 25th birthday (ha, I know what you're thinking) it was over for good."

Zang explained that the breakup came from her. "I don't how to explain it exactly, I just felt like I was ready for our relationship to be done. It was like I had outgrown that version of myself, the Hollywood high school girl. I wanted to figure out who I was and what I wanted." She said that she's happily married now and reminds readers that only DiCaprio and his partner know why they broke up.

For a brief period of time, Leonardo DiCaprio set his sights on supermodel Amber Valletta. As per Us Weekly, DiCaprio apparently saw Valletta in a fashion magazine at the time and got his people to get in touch with her. Hey, when you're Leo, you can really do anything. 

While Valletta and DiCaprio's connection didn't stand the test of time, the supermodel didn't stop believing in love. In a 2021 chat with the Wall Street Journal, Valletta shared that love remains a top priority. "Love for the world, love for life, love for art, love for family, love for my child, love for my lover, love for friends. Love," she said again. "Definitely love."

In an April 2022 interview with Sleek, Valletta was asked to define love. "Real love is truth and forgiveness," she began. "Fear and ego are divisive. Love is essentially all we really are – we are created from it." She said that fear creates division and that this is never the answer, nor is it our natural state. "We learn fear, we learn anxiety, we learn to separate and that's the opposite of love," she went on. "Love never dies. Love is eternal love is light; love is truth; love is miracles; love is peace." 

Danish model Helena Christensen was reportedly connected to Leonardo DiCaprio in 1997, according to Us Weekly. Though they weren't exactly a couple, the movie star and the supermodel sure seemed to have fun. As People recounted, they were spotted out and about at clubs together, and naturally, this high-profile pairing caught some attention.

Christensen went on to strike up a romance with actor Norman Reedus, and the two welcomed a child. Reedus said that the first time he met Christensen was "just perfect" but he could hardly handle it. "When she came into the restaurant, I didn't wanna look at her," "The Walking Dead" actor told Nylon in 1999. "She was sitting right across the table, and I didn't want to look at her, because I knew if we started up a conversation, it would be serious from that time on. I was just cowardly."

They split up in 2003, but continued to work as a team as co-parents. "When Mingus was smaller, it was a little harder, going from two places," Reedus told the New York Post in 2014. "Now, he has the best of both worlds." While their romantic relationship didn't pan out, Christensen and Reedus sure seem to respect one another. As Christensen once said of her ex in Porter (via Daily Mail), "'There are just some people in my life whom I would fight for until the end, no matter what."

Leonardo DiCaprio reportedly had a brief thing with Bijou Phillips, daughter of South African model Geneviève Waïte and Mamas & the Papas frontman John Phillips, in the late '90s. Already an established model and tabloid staple by the time she crossed paths with DiCaprio, Bijou wanted to get into the movie game. And, as she told The Guardian, the "Titanic" star apparently helped make that a reality. According to Bijou, DiCaprio connected her with director James Toback when she was a teenager, and Toback ended up putting her in his 1999 film "Black and White."

After things with DiCaprio fizzled, Bijou went on to date Elijah Wood and Sean Lennon. As per Rolling Stone, Bijou and Lennon's relationship ended after she had an affair with his friend, Max LeRoy, and the liaison served as the inspiration for Lennon's album "Friendly Fire." In 2005, Bijou met actor Danny Masterson at a poker tournament. As she recounted to Paper (via E! News), "He wasn't laughing at my jokes. I was like, 'who is this Danny Masterson and what does he think he's doing?'" Apparently, his standoffishness wasn't a deterrent: The two began dating and have been married since 2011.

Leonardo DiCaprio supposedly had a short fling — we're talking two months long — with supermodel Eva Herzigová in 1998, according to Us Weekly. Their reported liaison was kept extra hush-hush because the Victoria's Secret model was married to Tico Torres, drummer for Bon Jovi, according to Elle. She and Torres divorced in 1998. Herzigová told Contact Music (via Vogue), "My marriage with Tico was a failure because we were too young to build any foundations together."

In the same Contact Music interview, Herzigová stated,  "I'm not a fan of marriage. A relationship is about evolution and marriage halts the progression of love. I'm a very independent girl and I quite like solitude. Actually I'm like a cat – I like being caressed but I also need to go away — and then come back."

While this marriage didn't last or her previous relationship with DiCaprio, Herzigová finally found love with Gregorio Marsiaj, an Italian business man she met by chance in Italy after her flight was delayed. She told Tatler that meeting Marsiaj was an earth-shattering experience. "I couldn't speak," she said. "I didn't know what to do with myself. By the second question he asked me, I had to excuse myself because I could hardly breathe." They went on to have three children together and Herzigová charmingly made headlines for walking runways while pregnant in 2012. Marsiaj was so clearly the one for her. Sorry Leo, better luck next time.

Leonardo DiCaprio and supermodel Gisele Bündchen were a high-profile pairing, to say the least. The two dated from 2000 to 2005, and their relationship was heavily documented; they were photographed at basketball games and Bündchen even attended the Oscars with DiCaprio.

The two eventually parted ways and it would be years before Bündchen spoke about it. In 2009, she told Vanity Fair that while things did not work out for them romantically, she and DiCaprio remained on good terms. "We know what we had; we were very young, and we grew together in a lot of ways," she said. "We were just not meant to be boyfriend and girlfriend, but I respect him enormously, and I wish him nothing but the best." Bündchen also praised his environmental activism work and character. 

Part of the shift came because Bündchen found her way of life at the time unsustainable and unhealthy. "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 wrote in "Lessons: My Path to a Meaningful Life." The problem was that DiCaprio wasn't on the same page. "Was I alone in wanting to do some serious soul-searching while he stayed the same? In the end, unfortunately, the answer was yes," she wrote.

Leonardo DiCaprio went on to date model Bar Refaeli after first meeting in Las Vegas, according to Us Weekly. Of all things, it was a U2 concert that brought them together. They began dating 2005 and called things off once and for all in 2011. As per People, DiCaprio and Refaeli split in 2009 for a spell but sure enough, got back together.

"It was a half year for which I am very grateful," Refaeli told L'Isha (via People). "I needed it. I came to understand a lot of things about myself." The model said she needed to understand what it was to be comfortable being alone. While this worked for a time, the pair ultimately split for good in 2011 with the Daily Mail claiming that neither was ready to take it to the next level. As late as 2016, outlets were speculating whether or not DiCaprio had fully moved on from Refaeli; Page Six counted four relationships following their split where DiCaprio pursued blonde women who looked a lot like his ex. 

Though DiCaprio sure seems to enjoy being in relationships, marriage doesn't seem to be an end goal. "I don't know whether I'll ever get married," DiCaprio once told Reveal magazine (via Daily Mail). "I've seen too many supposedly happy marriages go down. I've been as shocked as anyone." Meanwhile, Refaeli married Israeli businessman Adi Ezra and started a family with him.

Blake Lively and Leonardo DiCaprio began dating in May 2011, but by October of that year, they split, per Page Six. According to Us Weekly, the first time DiCaprio and Lively were spotted together was in New York City in November 2010, at a group dinner with Baz Luhrmann. News had already broke that DiCaprio was slated to play Jay Gatsby in "The Great Gatsby" and rumors were bubbling that Lively might play Daisy Buchanan. When the role went to Carey Mulligan, any interest in the two of them died down until May 2011, when they were photographed hugging on a yacht during the Cannes Film Festival.

What came after was a whirlwind of cuteness. After they went to Disneyland together, a source told Us Weekly, "I've never seen him like this with a girl." They canoodled and romanced all over Europe. Lively and DiCaprio were spotted riding bikes together in New York City, per People, since Lively was shooting "Gossip Girl" there. In fact, "Gossip Girl" screenwriter Joshua Safran told Vanity Fair about a unique dating ritual he noticed Lively do for DiCaprio. "We learned a lot from Blake," he said. "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. Blake was way ahead of the curve. It was pre-Instagram. She was documenting her life in photographs in a way that people were not yet doing."

After his split from Blake Lively, Leonardo DiCaprio dated Victoria's Secret model Erin Heatherton from 2011 to 2012, per Us Weekly.  They broke up just shy of one year together, and reportedly split because of their incompatible schedules.

Backstage at a Victoria's Secret show in 2012, Heatherton spoke with E! News about what she did to cope with heartbreak. "I'm here at the Victoria's Secret show," she said. "I couldn't feel more beautiful and [I'm] with all my friends, so it's wonderful." The network then jumped over to speak with Heatherton's best friend and fellow model, Lily Aldridge, who joked that Heatherton is going to have no trouble at all finding a new boyfriend. "I'm pretty sure there's a line around the block... waiting for her," Aldridge added. "Leo's loss is somebody else's gain," the interviewer joked.

While Heatherton had a successful career at Victoria's Secret, she faced rough years after her breakup with DiCaprio. According to the Blast, stylist Clare Byrne hit Heatherton with a $10 million lawsuit after the latter allegedly didn't see their joint athleisure brand plans through. In 2019, the model filed for bankruptcy, and she owed back taxes to New York and had several credit cards and lines of credit unpaid.

In May 2013, Leonardo DiCaprio began dating Victoria's Secret model Toni Garrn. Alas, as Us Weekly noted at the time, things apparently hit a significant speed bump after the actor was spotted partying with an entourage of over twenty women. While they split in 2014, this wasn't the end for Garrn and DiCaprio.

In September 2017, tongues started wagging when the pair was spotted hanging out again in New York City. According to People, they were photographed at 1 OAK and reportedly left the club together. And according to TMZ, later that month, DiCaprio hung out with German model Lorena Rae one evening only to meet up with Garrn a few hours later for dinner. In the photos taken on the night in question, DiCaprio is seen wearing the same gray shirt, navy cargo shorts, and blue baseball cap with both women.

But Garrn ultimately moved on. In October 2020, she married Alex Pettyfer, and the couple eventually welcomed a daughter. On July 19, 2021, Garrn posted on Instagram, "The most magical experience of my life brought Luca Malaika into our world last week. She immediately stole our hearts forever." It looks like Garrn has everything she could imagine.

Leonardo DiCaprio then began dating Kelly Rohrbach in 2015, a model and athlete who graced Sports Illustrated.  Rohrbach attended Georgetown University on a golf scholarship. Of her golf career, she told Harper's Bazaar, "My dad was a very good golfer, and he always dragged me along. I didn't like it that much when I was a kid and my dad would always say, 'Trust me, you're gonna like it when you're older,' and now I'm really thankful I play it. It's a fun sport to know when you're older."

Rohrbach landed Sports Illustrated Swimsuit Rookie of the Year in 2015, around the same time that she landed DiCaprio. As People reported at the time, the two exhibited some PDA while biking around New York City. (Clearly, Leo loves his bike dates.) By all accounts, it seemed really serious; OK! even went so far as to report that DiCaprio supposedly proposed to Rohrbach in October 2015.

However, this must have either fizzled or not been true because Rohrbach and DiCaprio reportedly broke up by January 2016. According to Page Six, "The Revenant" star mended his broken heart by partying in St. Barts where he and friends hit up Nikki Beach and partied with a big group of women. For her part, Rohrbach rebooted with her family and focused on what was ahead, like her role in the 2017 "Baywatch" film.

In 2016, Leonardo DiCaprio began dating Adam Levine's ex, Nina Agdal. According to People, the two had a relationship that spanned the globe, hitting up spots in New York City, Montauk, a private island in the Bahamas, Malibu, Ibiza, and so on. 

As Page Six reported at the time, Agdal and DiCaprio got in a minor car accident in the Hamptons in August 2016. He was driving with Agdal in a Range Rover when another driver rear-ended them. Sources saw that DiCaprio checked Agdal first to see if she was okay then went to the other driver to help her. "Leo was nice about it," a witness said. "He motioned for her to come with him, and he helped her over to the guardrail so she could rest." Ambulances were called but thankfully, no one was hurt.

Agdal even got close to DiCaprio's mother, Irmelin Indenbirken, and as People noted, the three of them celebrated his birthday in French Polynesia in November 2016. They attended a Golden Globes afterparty in January 2017 and Madonna's Oscar afterparty that February. Everything seemed to be trucking along for the two, but by May 2017, their romance had run its course. "They remain in touch. They both felt the relationship ran its course," an insider told Us Weekly. "It's amicable. They still do talk and remain friends." In 2022, Agdal started spending time with Logan Paul.

Camila Morrone and Leonardo DiCaprio met in May 2017 at the Cannes amFAR Gala. The model was 19 years old at the time and the actor in his 40s. Relationship rumblings wouldn't surface for a few months: In December 2017, the Daily Mail reported DiCaprio was spotted leaving her home in Los Angeles.

Perhaps unsurprisingly, the 20+ years between them raised some eyebrows. Morrone maintained the skepticism was undeserved. "There's so many relationships in Hollywood — and in the history of the world — where people have large age gaps," the model told the Los Angeles Times. "I just think anyone should be able to date who they want to date." In fact, as Morrone's career developed, DiCaprio became a sensitive subject, as some wondered if she landed gigs thanks to his connections. "I feel like there should always be an identity besides who you're dating," she said. "I understand the association, but I'm confident that will continue to slip away and be less of a conversation."

Morrone sat with DiCaprio at the 2020 Oscars, but it is worth noting that she did not walk the red carpet with him. The two announced their breakup in August 2022, just a few months after she turned 25. Shortly after her split, Morrone was spotted with Hailey Bieber and Kendall Jenner in Los Angeles, so she's obviously getting some support after four years with DiCaprio.