GISELE BUNDCHEN (2000-2005) – Gisele was between 20 and 25 years old during their relationship:
In 2000, when he was 25, he dated his youngest girlfriend Gisele Bundchen, when she was just twenty.
The two dated for five years until they split in 2005. Leo even took her as a date to the 2005 Oscars.
They were regularly seen at basketball games and shared a passion for raising awareness about environmental issues.
Love life: In 2000, when he was 25, he dated his youngest girlfriend Gisele Bundchen when she was just 18 (pictured in 2005)
Bündchen called it a day in 2015, revealing to Access Hollywood, “We just weren’t meant to be boyfriend and girlfriend, but I respect him immensely and I wish him nothing but the best.”
She would date Tom Brady in 2006 and marry him in 2009.
BAR REFAELI (2005-2011) – Bar was between 20 and 25 years old during their relationship:
After his relationship with Bündchen ended, Leo dated Sports Illustrated model Bar until 2011.
A source told The New York Post of their breakup at the time: “It was amicable, they’re still friends and they’re still talking. They just grew apart and went their separate ways.
“Neither are ready to settle down, and both have busy careers that have taken them in different directions.”
Next: After his relationship with Bündchen ended, Leo dated Sports Illustrated model Bar on and off until 2011 (pictured in 2010)
The actor’s relationship with Bar ended after six years of dating — coincidentally at the same time the Israeli model turned 25.
The split came after weeks of rumors following Leo failed to accompany the supermodel to New York’s Met Gala in 2011 and instead spent the night at city hotspot Top of the Standard.
DiCaprio also had a guys weekend with Bradley Cooper and Ryan Kavanaugh in Mexico the previous month.
BLAKE LIVELY (2011) – Blake was 23 years old during their relationship:
Ryan Reynolds’ current wife dated Leo for just one year, when she was 23.
DiCaprio met the actress at the 2011 Cannes Film Festival.
They then enjoyed a twelve-month romance that included romantic dates in Venice, Los Angeles, and New York City.
Celebrity: Ryan Reynolds’ current wife dated Leo for just one year – when she was 23 (pictured at Cannes in 2011)
Lively visited DiCaprio in Australia (where he was filming The Great Gatsby) late in the summer of 2011.
In October 2011, a People source noted that the split was “amicable” and 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 couple have three children.
ERIN HEATHERTON (2012) – Erin was 22 years old during their relationship:
The Victoria’s Secret Angel alum was just 22 when she dated DiCaprio in 2012.
The pair dated for ten months before splitting in October 2012, reportedly due to “crazy schedules.”
A source told US Weekly at the time, “There’s no bad blood — they still care deeply about each other. They’re both just really busy, they had crazy schedules.
Short: The Victoria’s Secret Angel alum was just 22 when she dated DiCaprio in 2012 (pictured on a June 14 bike ride in New York)
“They still love and respect each other very much. It was just time to move on.’
After the breakup, 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 be devastated when her romance with the supermodel-loving actor collapsed.
TONI GARRN (2013-2014) – Toni was between 20 and 21 years old during their relationship:
German-born model Garrn was just 21 when she and Leo split after nearly two years of dating.
The couple enjoyed an 18-month romance from May 2013 to December 2014.
According to tabloids, Garrn broke off the relationship after Leo was seen leaving a Miami nightclub with 20 women.
History: German-born model Garrn was just 21 when she and Leo split after nearly two years of dating (pictured in 2014)
After their initial split, they were seen hanging out several times, but they eventually called it quits. They were once seen leaving a club in New York hand in hand after the initial split.
Around the same time, Leo was spotted spending time with model Lorena Rae.
The two rarely went on the red carpet together, but were occasionally spotted in public.
After their divorce, Toni dated NBA star Chandler Parsons before taking time out for their romance in 2016 after a year together.
KELLY ROHRBACH (2015) – Kelly was 25 years old during their relationship:
The Baywatch reboot star was 25 when she and DiCaprio dated from June to about December 2015.
According to US Weekly, the breakup 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.
So they both had to take a break. “They’re still friends and talking, but it’s over.”
Another source told People, “They’re really friendly and it’s super amicable. They’re both so busy and there’s a big movie coming out and she’s one of the biggest supermodels in the world.
Short and sweet: The Baywatch reboot star was 25 when she and DiCaprio dated from June to about December 2015
“There is no other person in the picture.”
The couple appeared to confirm the split and then separately ring in the new year – with the Revenant star celebrating 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 friends included Leo’s old friend Lukas Haas.”
NINA AGDAL (2016-2017) – Nina was 24-25 years old during their relationship:
The relationship between Leo and the Danish swimsuit model came to an end after she turned 25 in 2017.
During their romance, they vacationed together to Ibiza, St. Bart’s and the Bahamas.
DiCaprio and Agdal largely 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 turned 25 in 2017 (pictured in August 2016)
DiCaprio and Agdal were first spotted together in May at the Up & Down club in New York. The actor arrived at the nightclub with Agdal and a group of friends, before partying the night away in the VIP section.
The following month, DiCaprio and Agdal were spotted on a weekend getaway in Montauk, New York.
In August 2016, the couple was involved in a car accident at the end of August. Fortunately, although an ambulance was called to the scene, the Hamptons accident was minor.
The following year they separated. A source revealed that it was DiCaprio who broke things up. “He’s not ready to settle down yet and just doesn’t plan on getting married or having kids,” the insider said.
CAMILA MORONNE (2017- 2022) – Camila was 20-25 years old during their relationship:
Leonardo and his model-actress girlfriend Camila Morrone called it quits last August after five years together.
The Revenant star, who is 22 years older than Camila, first met Camila in 2008 when she was just 12.
His old friend Al Pacino, who dated Camila’s mother Lucila Solá for years, made the introductions, and Leonardo apparently remained friends with the family for many 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 they were together.
The two boosted the profile of their relationship the following year when they attended Ellen DeGeneres’ birthday party together, and later in the year they were spotted with a PDA at Coachella.
Later in 2018, an anonymous source told People that the relationship had seriously escalated, as the two were “very much in love and serious” and “talked about getting engaged.”
The source claimed that Leo had “never loved a girl like this before,” and that he was even considering having children with his new love.
In 2019, Leo’s commitment to not publicly discuss his relationship was tested when both he and Camila had films premiering at the Cannes Film Festival.