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Leonardo DiCaprio‘s has had a string of high-profile relationships in the past, mostly linked to stunning models under the age of 25.
From his famous five-year romance with model Gisele Bundchen when she was 18, to another five-year relationship with Bar Refaeli and a brief fling with actress Blake Lively, Leonardo has had many women in his world.
The A-lister’s, 49, girlfriend Vittoria Ceretti, 26, was recently spotted with a diamond ring on her engagement finger – posing questions if he has finally found the one.
The couple, who are currently enjoying a romantic summer holiday in Italy, were first linked in the summer of 2023.
Vittoria was previously seen with a different silver diamond ring on her wedding finger which caused rumours to swirl if they were engaged in 2022.
And as Leonardo sparks wedding rumours once again, MailOnline takes a look at his past romances.
Leonardo DiCaprio’s has had a string of high-profile relationships in the past, mostly linked to stunning models under the age of 25
From his famous five-year romance with model Gisele Bundchen (right) when she was 18, to another five-year relationship with Bar Refaeli and a brief fling with actress Blake Lively (left), Leonardo has had many women in his world
The A-lister’s girlfriend Vittoria Ceretti, 26, was recently spotted with a diamond ring on her engagement finger – posing questions if he has finally found the one
Vittoria Ceretti (2023 to present)
The latest women in his life is stunning brunette model Vittoria, who he has been dating since last year.
And within their year long romance, the couple’s relationship appears to be getting a lot more serious as she was spotted with a large rock on her left finger this week.
During their sun-soaked holiday in Italy, the Oscar-winner and the Italian model have been dining with famous friends on their yacht.
They were joined by Leonardo’s BFF Tobey Maguire, British model Neelam Gill, Entourage star Kevin Connolly and former Vogue Editor-in-Chief Edward Enninful, among others.
On Wednesday, Vittoria sparked wedding rumours as she was seen with a massive heart-shaped diamond ring on her engagement finger.
The couple first sparked engagement speculation earlier this year when Vittoria was seen wearing a silver diamond ring in LA.
But an insider told TMZ at the time that the couple were not engaged and that she’d owned that particular ring since 2022.
The heart-shaped ring appears to be a new addition to Vittoria’s jewelry collection and it has renewed interest in the idea of Leonardo — Hollywood’s most infamous Lothario — finally settling down.
The latest women in his life is stunning brunette model Vittoria, who he has been dating since last year
And within their year long romance, the couple’s relationship appears to be getting a lot more serious as she was spotted with a large rock on her left finger this week
Gigi Hadid (2022)
Leonardo and Gigi – who is now in a relationship with Bradley Cooper – first fueled romance speculation in September 2022.
He was first linked to the model just weeks after his split from then-girlfriend Camila Morrone.
A few months later in November, Leonardo and Gigi enjoyed dinner together in the Big Apple and grabbed a scrumptious meal at Cipriani.
But rumours were quickly squashed in February 2023, as a source told DailyMail.com, ‘Leo is very single right now and he is not keen on the hype suggesting that he is seeking out these very young women.’
The insider continued: ‘He is looking for something more mature in the relationship department. It is just ridiculous because he cannot go anywhere without being linked to the youngest beautiful woman there.’
‘He wants to ditch this image once and for all and he is really bothered that this continues to follow him.’
A source told Entertainment Tonight that both stars spend time together when ‘their busy schedules permit.’
‘They both enjoy each other’s company and have fun together when their busy schedules permit. Yolanda and Bella know Gigi is capable of making her own healthy decisions and they’re supportive of her, Gigi’s main priority is her baby girl.’
In June, the model was seen hanging out with the Titanic actor and his parents two nights in a row while in London.
An insider told DailyMail.com, ‘They tried dating some time ago to see if there could be anything there, but there just wasn’t. They are friends and have been for so long, but they are not in an open relationship with no-strings-attached.’
‘People just need to let this go. That is not how Leonardo handles relationships. This makes him sound cheap and that he is not. When he is with someone, he is with them. He enjoys his friendship with Gigi and that is that.’
In regards to their London outings, the source expressed, ‘It is just ridiculous that a man and a woman cannot be friends without everyone insisting there is more to it.’
However, relationship rumors sparked up once again when the pair were seen attending David Rosenberg’s party in Bridgehampton over the Fourth of July weekend.
‘Leo and Gigi were talking to each other. She seemed thrilled. Everyone thought they were together [as a couple],’ an insider told Page Six.
Although there was no physical affection or PDA between the two, the source added that, ‘the way they were talking to each other … You could feel the energy.’
Leonardo and Gigi – who is now in a relationship with Bradley Cooper – first fueled romance speculation in September 2022
He was first linked to the model just weeks after his split from then-girlfriend Camila Morrone
A few months later in November, Leonardo and Gigi enjoyed dinner together in the Big Apple and grabbed a scrumptious meal at Cipriani
Camila Morrone (2017-2022)
Leonardo and his model-turned-actress girlfriend Camila Morrone called it quits after five years together in 2022.
The pair ‘quietly’ ended their relationship earlier this summer, a source close to Leo claimed to The Sun at the time.
Insiders close to Leonardo claimed to the publication that he and Camila grew apart.
‘Leo and Camila ended their relationship over the summer,’ a source said. ‘There are no bad feelings between them. It just came to a natural conclusion.’
The Revenant star, who is Camila’s senior by 22 years, was first introduced to Camila back in 2008, when she was only 12.
His longtime friend Al Pacino, who had dated Camila’s mother Lucila Solá for years, made the introductions, and Leonardo apparently remained friends with the family for years.
Leonardo and Camila officially got together sometime in 2017, following his breakup with model Nina Agdal just days before the Cannes Film Festival, though representatives for both initially denied that they were together.
In December 2022, E! News reported that they had taken the major step of moving in together. Throughout 2022, the couple were spotted being affectionate and were reported to be as strongly connected as ever.
One of the last public sightings of the two appeared to be an outing at a beach in Malibu for the on July 3, though they were not pictured together at the time.
Leonardo and his model-turned-actress girlfriend Camila Morrone called it quits after five years together in 2022
The pair ‘quietly’ ended their relationship earlier this summer, a source close to Leo claimed to The Sun at the time
Nina Agdal (2016-2017)
Things ended between Leo and the Danish swimsuit model after she hit 25 in 2017.
During their mostly private romance they holidayed together in Ibiza, St. Bart’s and the Bahamas.
A source told PEOPLE at the time that their breakup was ‘amicable.’
Leo and Nina were first spotted together in May at Up & Down club in N.Y.C. The actor arrived at the nightclub with Nina and a group of friends, before partying the night away in the VIP section.
The next month, Leo and Nina were spotted on a weekend getaway in Montauk, New York.
In August 2016 the pair were involved in a car accident in late August. Luckily, though an ambulance was called to the scene the Hamptons crash was minor.
The next year they split. A source revealed it was Leo who broke things off. ‘He’s not ready to settle down and just isn’t in the mindset to get married or have kids,’ the insider said.
Things ended between Leo and the Danish swimsuit model after she hit 25 in 2017
During their mostly private romance they holidayed together in Ibiza, St. Bart’s and the Bahamas. A source told PEOPLE at the time that their breakup was ‘amicable’
Kelly Rohrbach (2015)
The Baywatch reboot star was 25 when she and Leo dated from June until around December of 2015.
According to US Weekly, the split was a mutual decision: A source told the magazine: ‘It was mutual. They both have intense work schedules and a lot going on in their lives right now.
‘They both needed to take a break because of that. ‘They are still friends and talking but it’s over.’
Another source told People: ‘They are very friendly and it’s super amicable. They are both so busy and he’s got a big movie coming out and she’s one of the biggest super models in the world.
‘There is no other person in the picture.’
Seemingly confirming the split, the pair rang in the New Years after separately – with the Revenant star partying it up in St.Barths and the model spending the night with family.
A source told People of his New Years: ‘Leo partied with blondes and brunettes and male buddies included Leo’s longtime friend Lukas Haas.’
The Baywatch reboot star was 25 when she and Leo dated from June until around December of 2015
Toni Garrn (2013-2014)
German-born model Toni was just 21 when she and Leo broke up after nearly two years of dating.
The pair enjoyed an 18-month romance from May 2013 to December 2014.
According to tabloids, Toni broke it off after Leo was spotted leaving a Miami nightclub with 20 women.
After their initial split they were spotted hanging out on several occasions but then finally called it quits. They once were seen leaving a club in NYC holding hands after the initial split.
Around the same time Leo was spotted spending time with model Lorena Rae.
The two rarely hit the red carpet together, but they were occasionally spotted out in public.
Following their split, Toni dated NBA star Chandler Parsons before calling time on their romance in 2016 after a year together.
German-born model Toni was just 21 when she and Leo broke up after nearly two years of dating (pictured in 2014)
According to tabloids, Toni broke it off after Leo was spotted leaving a Miami nightclub with 20 women
Erin Heatherton (2012)
The Victoria’s Secret Angel alum was just 22 when she dated Leo in 2012.
The pair dated for 10 months before parting ways in October 2012 due reportedly due to ‘crazy schedules’.
A source told US Weekly at the time: ‘There’s no bad blood – they still care about each other a lot. They’re both just really busy, they had crazy schedules.
‘They still love and respect each other very much. It was just time to move on.’
After the split she said: ‘He’s (Leo) a wonderful person and he’s a friend of mine, I wish him all the best.’
Erin was said to have been devastated when her romance with the supermodel-loving actor collapsed.
The Victoria’s Secret Angel alum was just 22 when she dated DiCaprio in 2012 (pictured on a bike ride in June 14 in NYC)
Blake Lively (2011)
The current wife of Ryan Reynolds dated Leo for just one year – when she was 23.
DiCaprio met the actress during the 2011 Cannes Film Festival.
They and went on to enjoy a 12-month romance that included romantic dates in Venice, Los Angeles and New York City.
Lively visited DiCaprio in Australia (where he was filming The Great Gatsby) late in summer 2011.
In October 2011, a People source noted that the split was ‘amicable’ and that the actors remained friends
Leo’s ‘work commitments’ reportedly played a role in the breakup.
The current wife of Ryan Reynolds dated Leo for just one year – when she was 23
Bar Rafaeli (2005-2011)
After his relationship ended with Gisele, Leo dated Sports Illustrated model Bar on-and-off ’til 2011.
A source told The New York Post of their breakup at the time: ‘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.’
The actor’s relationship with Bar ended after six years of dating – coincidentally the same time the Israeli model turned 25.
The split came after weeks of rumours after Leo failed to accompany the supermodel to the Met Gala in New York in 2011 and instead spent the night at city hotspot Top of the Standard.
Leo also had a boys’ weekend with Bradley Cooper and Ryan Kavanaugh in Mexico the month before.
After his relationship ended with Gisele, Leo dated Sports Illustrated model Bar on-and-off ’til 2011 (pictured in 2010)
Gisele Bündchen (2000-2005)
In 2000 when he was 25 he dated his youngest girlfriend Gisele when she was just around 20 at the time.
The two dated for five years until they split in 2005. Leo 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.
Gisele 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.’
She’d go on to date Tom Brady in 2006 and marry him in 2009.
In 2000 when he was 25 he dated his youngest girlfriend Gisele Bundchen when she was just around 18 at the time (pictured in 2005)