Leonardo DiCaprio is often considered one of Hollywood’s most notorious bachelors, with a mysterious and intriguing love life that spans three decades. This includes Leonardo DiCaprio’s girlfriend in 2024, model Vittoria Ceretti, who is about 23 years younger than him.
The couple recently returned to New York after a steamy European summer holiday, according to reports from the Daily Mail, which also notes the two of them were spotted cruising around the Mediterranean together. While the pair have been quiet about the relationship, it does seem that Vittoria, now 26, may have broken the ’25 year curse’.
But his relationship history is still a source of intrigue.
Since he shot to stardom for his iconic roles in What’s Eating Gilbert Grape, Romeo + Juliet and Titanic, DiCaprio has gone on to date numerous women including famous actresses, singers and models (including what’s basically a roll call of a Victoria’s Secret show).
Here, we’ve compiled a timeline of the Oscar-winning actor’s dating timeline.
Leonardo DiCaprio Girlfriend and Dating History, 1994-Now
Bridget Hall (1994)
DiCaprio’s first public fling was with model and Vogue cover girl Bridget Hall in 1994. According to The Sun, he dumped her after Bridget found their “night of love” disappointing.
Brittany Daniel (1994)
After filming together in The Basketball Diaries, DiCaprio and Daniel dated off-screen in 1994.
Naomi Campbell (1995)
The actor reportedly had a fling with supermodel Naomi Campbell back in 1995, however they went on to become good friends and even spotted hanging out on a yacht in 2013.
Kristen Zang (1996-1997)
The model and actress was considered to be “the love of his life” according to The New York Daily News. Zang was Leonardo DiCaprio’s girlfriend for fifteen months, including as his date to the Romeo + Juliet premiere. However, Kristen Zang dumped him for his lack of maturity and “posse of young model-hounds.”
Helena Christensen (1997)
The Victoria’s Secret model was spotted with DiCaprio at a number of parties in 1997.
Amber Valletta (1998)
According to US Weekly, DiCaprio spotted Valletta’s picture in a magazine and requested his management track her down. They briefly dated in 1998.
Bijou Phillips (1998)
Leo dated Bijou Phillips, daughter of singer John Phillips, in 1998 before she decided to move on to Black and White co-star Elijah Wood.
Eva Herzigova (1998)
According to US Weekly, Leonardo DiCaprio had an affair with Czech model Eva Herzigova for two months while she was married to Bon Jovi drummer Tico Torres.
Gisele Bündchen (2000-2005)
Brazilian supermodel Gisele Bündchen was Leonardo DiCaprio’s girlfriend for five years in the early 2000s. He even took her as a date to the Oscars in 2005.
The couple were regularly spotted at basketball games and shared a passion for raising awareness on environmental issues. Bündchen ended it in 2015 and revealed to Access Hollywood, “We were just not meant to be boyfriend and girlfriend, but I respect him enormously, and I wish him nothing but the best.”
Bar Refaeli (2005-2011)
After his relationship ended with Bündchen, Leo dated Sports Illustrated model Bar Refaeli on-and-off ’til 2011. A source told The New York Post, “It was amicable, they’re still friends and they are still talking. They just grew apart and went their separate ways. Neither are ready to settle down, and both have busy careers that have been taking them in different directions.”
Anne Vyalitsyna (2009)
While on a six-month break from his relationship with Refaeli, Leo briefly dated the Sports Illustrated and Victoria’s Secret model Anne Vyalitsyna in 2009.
Blake Lively (2011)
According to US Weekly, DiCaprio met the actress during the 2011 Cannes Film Festival and went on to enjoy a five-month romance that included romantic dates in Venice, Los Angeles and New York City.
Erin Heatherton (2012)
Leonardo DiCaprio and Erin Heatherton dated for 10 months before parting ways in October 2012, reportedly due to “crazy schedules”.
Toni Garrn (2013-2014)
Victoria’s Secret model Toni Garrn was Leonardo DiCaprio’s girlfriend for 18 months until they broke up in 2014. According to tabloids, Garrn broke it off after Leo was spotted leaving a Miami nightclub with 20 women.
Rihanna (2015)
Hollywood was abuzz when DiCaprio was seen with the singer at numerous Hollywood parties in 2015. But she was never confirmed to be Leo’s girlfriend.
Kelly Rohrbach (2015)
Sports Illustrated model Kelly Rohrbach dated Leonardo DiCaprio for a few months in 2015, before breaking up at the beginning of 2016. According to US Weekly, the split was a mutual decision: “They both have intense work schedules and a lot going on in their lives right now…They are still friends and talking but it’s over.”
Laura Whitmore (2016)
There was a lot of speculation about DiCaprio and Irish TV presenter Laura Whitmore after they met at a New York gala event. The pair were then rumoured to be partying together in Leo’s hotel suite after the BAFTAs.
But they never confirmed relationship and Whitmore was dating musician Rory Williams at the time, according to an Irish Times report. When asked about the night, addressed the dating rumours to Hello! Magazine and said, “Everyone was just having fun – there was a lot of dancing.”
Nina Agdal (2016)
Leonardo DiCaprio started dating the Danish model in July 2016. But after a string of vacations in New York, Bahamas and Montauk, they broke up in May 2017.
Georgia Fowler (2016)
After her romance with musician Harry Styles ended, Fowler moved on to DiCaprio. According to The Sun, the couple got cosy in a nightclub in Cannes and hung out with DiCaprio’s good friend Tobey Maguire.
Juliette Perkins (2017)
It was rumoured that Leo was dating New Zealand model Juliette Perkins in late 2017. The actor was photographed leaving a Los Angeles club with Perkins and spotted hopping into a car together.
Camila Morrone (2017 – 2022)
Many people thought that actress Camila Morrone would be the one to break Leonardo DiCaprio’s ’25 year curse’ while she was his girlfriend. And if you’re wondering, this refers to Leo’s reported dating trend of exclusively date women under 25 years old.
Dating rumours began when DiCaprio was spotted with model in December 2017 (when she was 20 and he was 43). After being spotted at Coachella and numerous vacations together, it was reported that DiCaprio is finally settling down and ready to pop the question.
Reports claim that Camila and Leo ended their almost four-year relationship despite speculation that they were “getting serious”. But it seems that wasn’t meant to be.
Camila has gone on to appear in the series Daisy Jones & The Six alongside Riley Keough and Suki Waterhouse. She’s also the titular character in 2024 film Marmalade – so we’re sure this wont be the last we see of her.
Gigi Hadid (2022)
Shortly after his split from Morrone was reported, DiCaprio and Gigi Hadid reportedly struck up a romance, though it appears it was nothing more than a casual fling—if anything at all.
A source told Page Six that while the pair “like each other very much,” neither wants “anything serious right now”.
They added: “Gigi doesn’t have the energy to run after DiCaprio. His routine is too much for her.”
Victoria Lamas (2022)
In December 2022, Leonardo DiCaprio was linked to 23-year-old model Victoria Lamas after they were spotted leaving an LA restaurant together. However suggestions she was Leo’s girlfriend were quickly shut down, with a source telling E! News that there’s “no truth to it this time”.
“They were seated (not next to each other) at a big group dinner,” they explained, adding that there were “a number of other people in the car” when they left.
Eden Polani speculation (2023)
(@edenpolanii)Rumours of Leonardo DiCaprio having a girlfriend much younger than him swirled when he was seen sitting next to 19-year-old model Eden Polani at a party in January 2023. But it appears to have simply been rumours, with a source telling PEOPLE: “Leo and Eden just so happened to have been seated next to each other at the party, and were hanging in the same group… Just because Leo might be talking to or sitting with a girl doesn’t mean he’s dating her.”
Gigi Hadid again (2023)
Rumours swirled of a renewed romance between the supermodel and Leo, after they were seen hanging out in New York multiple times early in the year. Multiple outlets reported the pair were dating “casually” around June and July.
Vittoria Ceretti (2023)
Leonardo DiCaprio and girlfriend Vittoria Ceretti met in the European summer of 2023. At the time, Page Six shared a video of the pair making out at the Hï Ibiza club on 9 August 2023. They were also spotted hanging out in California a couple of weeks later. Now, more than a year on, we’re still seeing snaps of the couple.
This article originally appeared on Marie Claire Australia and is republished here with permission.
