Leonardo DiCaprio can get pretty much any woman he wants, and during some points in his life, it seemed as though he was trying to get them all. Despite a few long relationships and the ability to keep most of his flings under wraps, Leo still has a reputation as a Hollywood playboy with an affinity for mostly models — but sometimes actresses — and almost always blondes, with a few exceptions. With his latest would-be love, he also seems to have made an exception to his long-rumored "I can't seriously date anyone over 25" rule, because in the summer of 2022, rumors linked Leo to supermodel Gigi Hadid, who was 27 to his 47 (and a single mom to a toddler daughter) at the time. By September 2022, Leo and Gigi were even seen making out at two New York Fashion Week events, Instagram gossip account Deux Moi reported, and it was on. As Leo explores this new era of dating "older" women, join Wonderwall.com as we revisit the Oscar winner's former flames…
Keep reading to see all the women from his past…
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Juliette Lewis, 1993
In the first of many on-set hookups, Leonardo DiCaprio reportedly dated his "What's Eating Gilbert Grape" co-star Juliette Lewis following her split from Brad Pitt — so this was a good early score for Leo and a sign of grape, er, great things to come.
Bridget Hall, 1994
Years after Leonardo DiCaprio's reported 1994 fling with Bridget Hall, The Sun ran a story claiming the actor took the model's virginity in London's Royalton Hotel (and further alleged that she wasn't too thrilled with the experience). Bridget denied the whole thing and Leo has said that their relationship was "blown out of proportion." Next!
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Brittany Daniel, 1994-1995
Brittany Daniel and twin sister Cynthia Daniel played sisters on the '90s television series "Sweet Valley High," but it was Brittany who reportedly played a little one-on-one with Leonardo DiCaprio when the two filmed 1995's "The Basketball Diaries" together.
Claire Danes, 1995-1996
Once again, on-screen steaminess allegedly led to off-set lovin' for Leonardo DiCaprio, who reportedly hooked up with Claire Danes while they were filming "Romeo + Juliet." This relationship rumor feels more hopeful than anything, since fans of the film always want a storybook romance. But they spent enough time together that it's hard to believe there wasn't a little something going on off-set.
Kristen Zang, 1996-1997
In 1996, Leonardo DiCaprio showed up to the "Romeo + Juliet" premiere hand in hand with Kristen Zang. The model's dad blabbed to the press about a private Thai island Leo had taken her to while he was filming "The Beach," but she supposedly didn't like his friends (you know, the "posse"), so it was no surprise when they split after a little more than a year of dating.
Alicia Silverstone, 1997
During one Leonardo DiCaprio's wild periods in the late '90s, he allegedly had a wandering eye that Kristen Zang didn't appreciate. As soon as they were done, Leo reportedly focused his attention on Alicia Silverstone, who was in her prime and busy being on FHM's hottest women list year after year. She was also coming off her "Batman & Robin" role, so the timing was right for a short-lived relationship between two of Hollywood's most beautiful and in-demand people.
Emma Bunton, 1997
Only a few lucky guys have dated a Spice Girl, and Leonardo DiCaprio's favorite flavor in 1997 was said to be Baby Spice. Emma Bunton was a young 20-something back then and the blondest of the bunch, so this alleged hookup totally makes sense. The following year, she got together with longtime love Jade Jones, with whom he has two kids, for the first time.
Natasha Henstridge, 1997-1998
Once that big boat went down (we're talking about 1997's "Titanic," people), Leonardo DiCaprio rode the wave of success into the arms of a number of women in 1997 and 1998. It was a streak of record proportions that should land him in some sort of dating hall of fame. He was also tied to one-nighters with models Helena Christensen and Amber Valletta, but "Species" star Natasha Henstridge gets her picture up because rumors swirled that Leo had fathered her child — until she came out and revealed that Liam Waite was actually her baby's dad.
Kidada Jones, 1998
Kidada Jones — the daughter of music mogul Quincy Jones and actress Peggy Lipton (and the sister of actress Rashida Jones) — famously dated Tupac Shakur. But in September 1998, rumors were flying that she was at the center of a love triangle between the music star then known as Sean "Puffy" Combs and Leonardo DiCaprio, who was still riding high on his "Titanic" fame. While it sounds fun, it wasn't long before the ship sank on the Kidada relationship.
Eva Herzigova, 1998
Leonardo DiCaprio was romantically linked to Czechoslovakian model Eva Herzigova after they were seen laughing and dancing together at the London premiere of his film "The Man in the Iron Mask" in 1998. She was married to Bon Jovi drummer Tico Torres at the time — their marriage would end just a few months later. But despite reports claiming she dated Leo for about a month, Eva later insisted he was just an old friend. "He's a great guy but we never had an affair," she told The Mirror.
Naomi Campbell, 1998
In March 1998, the New York Post reported that Leonardo DiCaprio and Naomi Campbell were doing some "heavy-duty canoodling" in Paris, sparking rumors of a hookup. The two later did some serious yachting together in Sardinia in 2010 with their new significant others at the time, Israeli model Bar Refaeli and Russian billionaire Vladimir Doronin.
Bijou Phillips, late '90s
Bijou Phillips — the daughter of The Mamas & the Papas leader John Phillips and singer Michelle Phillips — was a wild child back in the day. All that sex, drugs and rock 'n' roll cred apparently won over Leonardo DiCaprio in the mid-'90s after he saw her dancing at Bowery Bar, called writer/director James Toback and got her a role in "Black and White," The Guardian reported. Years later, at the end of the decade, they dated.
Gisele Bundchen, 2000-2005
It seems like forever ago now, but before she was Mrs. Tom Brady, Gisele Bundchen was the stunning model who tamed Leonardo DiCaprio for longer than anyone else to date. They hit red carpets and went on public outings together and were the "it" couple during their run. In 2005, they were cursed by being added to People's "Most Beautiful Couples" list, which preceded their demise.
Demi Moore, 1998 & 2002
This one is more of a rumor than anything, but there's a story that Demi Moore cheated on Bruce Willis for one night with Leonardo DiCaprio in 1998 and then hooked up with him again in 2002 when she was single and he was on a break with Gisele Bundchen.
Sara Foster, 2002
Sara Foster is now married to tennis star Tommy Haas, but back when Leonardo DiCaprio was on a break with Gisele Bundchen, he reportedly scored with the former "90210" star. He was seen taking her to dinner at Mastro's Steakhouse in Beverly Hills with former President Bill Clinton in 2002.
Sienna Miller, 2005
Leonardo DiCaprio and Gisele Bundchen were going through hard times and nearing the end of their romance when The Sun reported that Leo was cozying up to Sienna Miller at Los Angeles' Mood nightclub in 2005. That allegedly ended the Gisele relationship for good. Sienna was on a break from Jude Law at the time, but her night with Leo certainly didn't end that relationship, as they later reconciled for a time.
Bar Refaeli, 2006-2011
Bar Refaeli was practically unknown when Leonardo DiCaprio started dating her, so he can take some credit for upping the Israeli model's profile. They were on-again, off-again for close to five years between 2006 and 2011. Bar went on to marry Israeli businessman Adi Ezra, with whom she now has three children.
Emma Miller, 2009
While on a break with Bar Refaeli in July 2009, Leonardo DiCaprio hit the London club scene with British model Emma Miller, who once dated actor Jesse Metcalfe and went onto join the cast of "Made in Chelsea" years later. It was a big upgrade for her, but her stint on the A-list only lasted a few weeks at best.
Anne Vyalitsyna, 2009
Victoria's Secret model Anne Vyalitsyna spent a fun few days with Leonardo DiCaprio in Ibiza in 2009. He was on a break with Bar Refaeli and Anne V was single. Things didn't work out romantically with Anne and Leo, but Anne's career started to take off not long after. She also later famously dated another notorious playboy: Maroon 5's Adam Levine.
Paris Hilton, 2010
Big star or not, you can't spend your life in Hollywood without being linked to a Hilton. In the summer of 2010, Paris Hilton and Leonardo DiCaprio were spotted together in Las Vegas and then again in Johannesburg, South Africa, watching the World Cup. It was just enough to get the gossip columns riled up for the release of "Inception."
Blake Lively, 2011
It was a little surprising when Leonardo DiCaprio started dating Blake Lively after his breakup with Bar Refaeli. She's a big star and all, but thanks to her run on "Gossip Girl," she was a tabloid darling at the time, which isn't really Leo's style. (Then again, she is a tall, beautiful blonde — just his type.) They hit up the Grand Prix in Monaco and partied on the French Riviera, so it was a fun ride for the few months it lasted in 2011.
Alyce Crawford, 2011
While Leonardo DiCaprio was filming "The Great Gatsby" in Australia, he was "friendly" with the locals. Alyce Crawford, a former contestant on "Australia's Next Top Model," was identified by People magazine as a likely recipient of Leo's affections. Aussie model Kendal Schuler was as well. (No pic available, but big surprise: She's beautiful.)
Erin Heatherton, 2012
Leonardo DiCpario enjoyed a 10-month romance with Victoria's Secret model Erin Heatherton in 2012. Although it was short-lived, both claimed to have parted amicably and cited busy schedules for the reason their relationship didn't work out. On to the next!
Toni Garrn, 2013-2014
Leonardo DiCaprio and Victoria's Secret model Toni Garrn were spotted arriving on a yacht after watching the Monaco Formula 1 Grand Prix in May 2013. It was one of the first sightings of the pair, who spent that summer traveling together across Europe — from France to Ibiza. However, by 2014, they were dunzo after she reportedly got upset when Leo left a Miami hotspot with 20 young ladies. That'll do it! The German model went on to marry actor Alex Pettyfer in 2020.
Nina Agdal, 2014 & 2016
Nina Agdal and Leonardo DiCaprio were first linked in 2014 then rekindled the flame at the 2016 Cannes Film Festival. After that, they were seen together in New York City, The Hamptons, Malibu, French Polynesia and St. Barts. In May 2017, though, it was reported that the duo had called it quits after a year together (the second time around).
Kelly Rohrbach, 2015
Model Kelly Rohrbach spent the summer of 2015 on Leonardo DiCaprio's arm. But by that November, their romance had fizzled. "It was mutual," a source told Us Weekly at the time. "They both have intense work schedules and a lot going on in their lives right now." They're seen here at the 2015 U.S. Open Tennis Championships with Leo's pal Lukas Haas.
Leonardo DiCaprio was linked to Rihanna in early 2015. A report from TMZ claimed the two got "super-steamy and even swapp[ed] spit" at a party on Jan. 10, 2015, at the famed Playboy Mansion. Later, they ended up at the same afterparty where, the website alleged, "things got even hotter." A year later, there were reports that they hooked up again in Paris.
Laura Whitmore, 2016
At an afterparty following the 2016 BAFTA Awards, Leonardo DiCaprio reportedly took an interest in TV presenter Laura Whitmore. The Irish television personality diplomatically navigated the rumors when she told HELLO! that "everyone was just having fun — there was a lot of dancing."
Georgia Fowler, 2016
In 2016, Leonardo DiCaprio was then spotted with model Georgia Fowler. The pair were seen cozying up to one another at a Cannes Film Festival party, though speculation about their romance eventually fizzled.
Lorena Rae, 2017
Lorena Rae and Leonardo DiCaprio were first spotted out and about together in July 2017, sources told People. The actor and the German model were seen on multiple dates throughout the summer and early fall before Leo was rumored to be pursuing a new beauty…
Juliette Perkins, 2017
Leonardo DiCaprio was linked to then-19-year-old model Juliette Perkins in October 2017 after they were spotted leaving a Los Angeles nightclub together.
Camila Morrone, 2017-2022
Leonardo DiCaprio was first seen with actress-model Camila Morrone — who's 23 years his junior — while shopping in Los Angeles in December 2017. A month later, the new couple was spotted vacationing together in Aspen, Colorado. While chatting with the Los Angeles Times in 2019, Camila defended their romance. "There's so many relationships in Hollywood — and in the history of the world — where people have large age gaps," she said. "I just think anyone should be able to date who they want to date." In June 2022 — the month she turned 25 — Deux Moi reported that they'd recently split, which is significant since, as Lainey Gossip has pointed out, Leo's never publicly dated any woman more than a few months past her 25th birthday. They were spotted together again that July, indicating things were still on, but at the end of August 2022, People magazine confirmed the pair had indeed gone their separate ways.