GISELE BUNDCHEN (2000-2005) – Gisele was 20-25 years old during her relationship:
In 2000, when he was 25, he dated his youngest girlfriend, Gisele Bundchen, who was just 20 at the time.
The two were together for five years until they separated in 2005. Leo even took her as his date to the Oscars in 2005.
They were regularly spotted at basketball games and shared a passion for raising awareness of environmental issues.
Love Life: In 2000, when he was 25, he dated his youngest girlfriend, Gisele Bündchen, when she was just 18 (pictured in 2005)
Bündchen called it quits in 2015, telling Access Hollywood, “We just weren’t meant to be boyfriend and girlfriend, but I respect him tremendously and wish him nothing but the best.”
She dated Tom Brady in 2006 and married him in 2009.
BAR REFAELI (2005-2011) – Bar was 20-25 years old during their relationship:
After his relationship with Bündchen ended, Leo dated Sports Illustrated model Bar on and off until 2011.
A source told the New York Post about their split at the time: “It was amicable, they are still friends and still talk.” They simply grew apart and went their separate ways.
“Neither is ready to settle down and both have had 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, the Israeli model turned 25 at the same time.
The split came after weeks of rumors after Leo didn’t 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 23 during their relationship:
Ryan Reynolds’ current wife only dated Leo for a year – when she was 23.
DiCaprio met the actress during 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 only dated Leo for a year – when she was 23 (pictured in Cannes in 2011)
Lively visited DiCaprio in Australia (where he was filming The Great Gatsby) in late summer 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 together.
ERIN HEATHERTON (2012) – Erin was 22 during her relationship:
The Victoria’s Secret Angel alum was just 22 years old when she started dating DiCaprio in 2012.
The couple dated for ten months before parting ways in October 2012, reportedly due to “crazy schedules.”
A source told US Weekly at the time: “There’s no bad blood – they still care about each other very much.” They’re both just very busy, they’ve had crazy schedules.
Synopsis: The former Victoria’s Secret Angel was just 22 when she started dating DiCaprio in 2012 (pictured on a bike ride in New York on June 14)
“They still love and respect each other very much. “It was just time to move on.”
After the breakup, she said: “He (DiCaprio) is a wonderful person and a friend of mine, I wish him all the best.”
Erin was said to be devastated when her romance with the supermodel-loving actor failed.
TONI GARRN (2013-2014) – Toni was 20-21 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 had an 18-month romance from May 2013 to December 2014.
According to tabloids, Garrn broke off the relationship after Leo was spotted leaving a Miami nightclub with 20 women.
Story: German-born model Garrn was just 21 when she and Leo split after nearly two years of dating (pictured in 2014)
After their first breakup, they were spotted hanging out together several times but eventually called it quits. They were once seen leaving a club in New York holding hands after their first breakup.
Around the same time, Leo was spotted spending time with model Lorena Rae.
The two rarely walked the red carpet together, but were occasionally spotted in public.
After their split, Toni dated NBA star Chandler Parsons before ending their romance in 2016 after a year together.
KELLY ROHRBACH (2015) – Kelly was 25 during her relationship:
The Baywatch reboot star was 25 when she and DiCaprio dated from June to around December 2015.
According to US Weekly, the split was a mutual decision: A source told the magazine: “It was mutual. They both have intensive work schedules and there is a lot going on in their lives at the moment.
“That’s why they both had to take a break.” “They’re still friends and talk, but it’s over.”
Another source told People: “They’re very friendly and it’s super amicable.” They’re both so busy and he just has a big movie coming out and she’s one of the biggest supermodels in the world.
Short but sweet: The Baywatch reboot star was 25 when she and DiCaprio dated from June to around December 2015
“There is no other person in the picture.”
Confirming their split, the pair rang in the New Year separately – with the Revenant star celebrating in St Barths and the model spending the night with family.
A source told People about his New Year: “Leo celebrated with blondes and brunettes, and his male pals included Leo’s long-time boyfriend Lukas Haas.”
NINA AGDAL (2016-2017) – Nina was 24-25 years old during her relationship:
Leo and the Danish swimsuit model’s relationship ended after she turned 25 in 2017.
During their romance, they vacationed 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 split was “amicable.”
It’s over: Leo and the Danish swimsuit model’s relationship ended 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 next month, DiCaprio and Agdal were spotted on a weekend getaway in Montauk, New York.
In August 2016, the two were involved in a car accident at the end of August. Although an ambulance was called to the scene, the accident in Hamptons was fortunately minor.
The next year they separated. A source revealed that it was DiCaprio who called things off. “He’s not ready to settle down and just doesn’t feel like getting married or having kids,” the insider said.
CAMILA MORONNE (2017-2022) – Camila was 20-25 years old during her 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, was first introduced to Camila in 2008 when she was just 12 years old.
His long-time friend Al Pacino, who had dated Camila’s mother Lucila Solá for years, introduced him to each other, and Leonardo apparently remained friends with the family for years.
Leonardo and Camila officially got together sometime in 2017 after he split from model Nina Agdal just days before the Cannes Film Festival, although reps for both initially denied they were together.
The two increased the profile of their relationship the following year when they attended Ellen DeGeneres’ birthday party together, and later that year they were spotted showing off some PDA at Coachella.
Later in 2018, an anonymous source told People magazine that the relationship had become increasingly serious as the two were “very in love and serious” and had “talked about getting engaged.”
The source claimed that Leo has “never loved a girl like that” and that he is even considering having children with his new love.
In 2019, Leo’s determination not to discuss his relationship publicly was tested when both he and Camila premiered at the Cannes Film Festival.