Hollywood’s most notorious bachelor Leonardo DiCaprio continues to thrill us not only with his films, but with his ever mysterious love life.
Since he shot to stardom for his iconic roles in Romeo + Juliet and Titanic, DiCaprio has gone on to date numerous women including famous actresses, singers and models (including a roll call of the Victoria’s Secret show).
Below, we’ve compiled a timeline of the Oscar-winning actor’s dating history.
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. DiCaprio dated Zang for fifteen months and took her as his date to the Romeo + Juliet premiere. However, the pair broke up after Zang dumped him for his lack of maturity and “posse of young model-hounds.”
Helena Christensen (1997)
The Victoria’s Secret model had been 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, he had an affair with the Czech model for two months while she was married to Bon Jovi drummer Tico Torres.
Gisele Bündchen (2000-2005)
Leo dated the Brazilian supermodel for five years and even took her as a date to the Oscars in 2005.
They 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 the Sports Illustrated model 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 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)
The pair dated for 10 months before parting ways in October 2012 due reportedly due to “crazy schedules”.
Toni Garrn (2013-2014)
Leo dated the Victoria’s Secret model 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.
Hollywood was abuzz when DiCaprio was seen with the singer at numerous Hollywood parties in 2015.
Kelly Rohrbach (2015)
The Sports Illustrated model dated the actor for a few months 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)
DiCaprio reportedly dated the Irish TV presenter after meeting an after-party. Whitmore addressed the dating rumours to Hello! Magazine and said, “Everyone was just having fun – there was a lot of dancing.”
Nina Agdal (2016)
He started dating the Danish model in July 2016 and after a string of vacations in New York, Bahamas and Montauk, they broke up in May 2017.
Georgia Fowler (2016)
After she 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 the New Zealand model 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)
While many thought that actress Camila Morrone would be the one to break the ’25 year curse’ (a.k.a Leo’s reported dating trend that sees him exclusively date women under 25 years old), it seems it wasn’t meant to be.
Reports claim that Camila and Leo ended their almost four-year relationship despite allegations that the former couple we’re “getting serious”.
The pair first sparked dating rumours when DiCaprio was spotted with model in December 2017 (when she was 20). After being spotted at Coachella and numerous vacations together, it was reported that DiCaprio is finally settling down and ready to pop the question.
Camila is set to appear in the upcoming Daisy Jones & The Six show alongside Riley Keough and Suki Waterhouse, 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, the actor was linked to 23-year-old model Victoria Lamas after they were spotted leaving an LA restaurant together. However suggestions of romance between them are already 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.
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)
Leo was seen canoodling with Italian model Vittoria Ceretti, 25, at a nightclub in Ibiza, Spain. In a video obtained by Page Six, the pair were seen making out at the Hï Ibiza club at around 4:30am on August 9. On August 22, they were spotted hanging out again, this time in California, where they went for a stroll to get ice cream.