GISELE BUNDCHEN (2000-2005) – Gisele was age 20-25 during their relationship:
In 2000 when he was 25 he dated his youngest girlfriend Gisele Bundchen 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.
Love life: 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)
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.’
She’d go on to date Tom Brady in 2006 and marry him in 2009.
BAR REFAELI (2005-2011) – Bar was age 20-25 during their relationship:
After his relationship ended with Bündchen, 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.’
Next up: After his relationship ended with Bündchen, Leo dated Sports Illustrated model Bar on-and-off ’til 2011 (pictured in 2010)
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.
DiCaprio also had a boys’ weekend with Bradley Cooper and Ryan Kavanaugh in Mexico the month before.
BLAKE LIVELY (2011) – Blake was age 23 during their relationship:
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.
Fame: The current wife of Ryan Reynolds dated Leo for just one year – when she was 23 (pictured in Cannes in 2011)
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
DiCaprio’s ‘work commitments’ reportedly played a role in the breakup.
Blake is now married to actor Ryan Reynolds and the pair share three children.
ERIN HEATHERTON (2012) – Erin was age 22 during their relationship:
The Victoria’s Secret Angel alum was just 22 when she dated DiCaprio 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.
Brief: 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)
‘They still love and respect each other very much. It was just time to move on.’
After the split she said: ‘He’s (DiCaprio) 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.
TONI GARRN (2013-2014) – Toni was age 20-21 during their relationship:
German-born model Garrn 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, Garrn broke it off after Leo was spotted leaving a Miami nightclub with 20 women.
History: German-born model Garrn was just 21 when she and Leo broke up after nearly two years of dating (pictured in 2014)
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.
KELLY ROHRBACH (2015) – Kelly was age 25 during their relationship:
The Baywatch reboot star was 25 when she and DiCaprio 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.
Short but sweet: The Baywatch reboot star was 25 when she and DiCaprio dated from June until around December of 2015
‘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.’
NINA AGDAL (2016-2017) – Nina was age 24-25 during their relationship:
Things ended between Leo and the Danish swimsuit model after she hit 25 in 2017.
During their romance they holidayed together in Ibiza, St. Bart’s and the Bahamas.
DiCaprio and Agdal mostly kept their relationship out of the spotlight.
A source told PEOPLE at the time that their breakup was ‘amicable.’
It’s over: Things ended between Leo and the Danish swimsuit model after she hit 25 in 2017 (pictured in August 2016)
DiCaprio and Agdal were first spotted together in May at Up & Down club in N.Y.C. The actor arrived at the nightclub with Agdal and a group of friends, before partying the night away in the VIP section.
The next month, DiCaprio and Agdal 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 DiCaprio 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.
CAMILA MORONNE (2017- 2022) – Camila was age 20-25 during their relationship:
Leonardo and his model-turned-actress girlfriend Camila Morrone called it quits after five years together last August.
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.
The two raised their relationship’s profile the following year, when they attended Ellen DeGeneres’ birthday party together, and they were seen later in the year showing off some PDA at Coachella.
Later in 2018, an anonymous source told People that the relationship had escalated in seriousness, as the two were ‘very in love and serious’ and ‘talked about getting engaged.’
The source claimed that Leo had ‘never loved a girl like this,’ and he was even considering having children with his new love.
In 2019, Leo’s commitment to not publicly discussing his relationship was tested when both he and Camila had films premiering at the Cannes Film Festival.