Leo’s Love Timeline

5 Eva Herzigova

• Duration: Two months
• When: 1998-1998
• Ages: Eva 25, Leonardo 24

Leo turned heads in 1998 when he had an alleged romance with model Eva Herzigova. The two met at the premiere of the film The Man in the Iron Mask. Rumors circulated that their unconfirmed fling happened while she was married to Tico Torres, drummer for Bon Jovi. 

6 Where Eva Herzigova Is Now

• Current age: 47 years old
• Occupation: Editor-at-Large for Vogue Czechoslovakia
• Relationship status: Engaged to businessman Gregorio Marsiaj after 16 years together

Eva Herzigova currently lives in Italy with her three sons and fiance. She opened up to The Sun about what her priorities are in life. “The most important things in my life are my kids’ well-being, mine, and my husband’s health and having a sense of responsibility towards each other and the planet which is falling apart,” she said, before clarifying that they have yet to be married. 

• The couple broke up before Herzigova turned 26. She was 25 years old.

7 Gisele Bündchen

• Duration: 5 years
• When: 2000-2005
• Ages: Gisele 20, Leonardo  26

These two met when DiCaprio saw Bündchen walk the runway in a fashion show. True to form, he asked his people to contact her people, and the rest is history. After years of engagement rumors, Bündchen broke up with him in 2005. She told Vanity Fair about the split, “We know what we had; we were very young, and we grew together in a lot of ways. We were just not meant to be boyfriend and girlfriend, but I respect him enormously, and I wish him nothing but the best,” she said.

8 Where Gisele Bündchen Is Today

• Current Age: 40 years old
• Occupation: Model, activist, and businesswoman
• Relationship status: Married to NFL star Tom Brady

Bündchen has been married to Tom Brady since 2009, and they have two children together. She walked her final runway show in 2016 and stepped back from the industry to spend time with her family. The former model opened up to People about motherhood, saying, “The quality of time I get to spend with my family is very important. That way I feel I am experiencing all the different aspects of my life without guilt.”

• The couple broke up before Bündchen turned 26. She was 23 years old.

9 Bar Refaeli

• Duration: 5 years
• When: 2006-2011
• Ages: Bar 20, Leonardo 32

It was on to the next model for DiCaprio. According to the New York Post, he met his next girlfriend, Bar Rafaeli, at a party for the band U2 in Las Vegas. They had a serious relationship until they officially broke up in 2011. A source told the New York Post about their split, “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 insider said.

10 What Bar Refaeli Is Up To Now

• Current age: 35 years old
• Occupation: Model
• Relationship status: Married to businessman Adi Ezra

Bar Refaeli wed her husband, Adi Ezra, on September 24, 2015. She posted a wedding pic on Instagram along with the caption, “The happiest day of my life!” she wrote. “I married my best friend. Live, Laugh, Love together forever.” The couple shares three children.

• The couple broke up before Refaeli turned 26. She was 25 years old.

11 Blake Lively

• Duration: 5 months
• When: 2011
• Ages: Blake 23, Leonardo 37

DiCaprio and Blake Lively met at the 2011 Cannes Film Festival, and they shared a whirlwind romance. They broke up after 5 months of dating. A source told E! News they called it off because of “distance and timing”.  

12 Where Blake Lively Is Now

• Age: 33 years old
• Occupation: Actress
• Relationship status: Married to Ryan Reynolds

Blake Lively married Ryan Reynolds in 2012 and they have 3 daughters. They are a private couple who seem to be down-to-earth. A source told Us Weekly, “Away from the cameras, people may find it surprising to hear they’re just a regular couple who love to hang out and do the normal things together without making a song and dance about it all,” the insider revealed.

• The couple broke up before Lively turned 26. She was 23 years old.

13 Madalina Ghenea

• Duration: 1 month
• When: 2011
• Ages: Madalina 24, Leonardo 37

According to the Daily Mail, DiCaprio was spotted with Romanian model Madelina Ghenea around Sydney’s Bondi Beach in 2011. He was in Australia shooting Baz Luhrmann’s The Great Gatsby. The couple had a quick rebound fling while DiCaprio got over his breakup with Blake Lively. They split after just a month of dating.

14 What Madalina Ghenea Is Doing Now

• Current age: 33 years old
• Occupation: Model
• Relationship status: Single

After the breakup with DiCaprio, Ghenea had high-profile relationships with Michael Fassbender, Gerard Butler, and Eros Ramazzotti. She began dating Matei Stratan in 2015, with whom she had a daughter named Charlotte. They sadly divorced in August 2020.

• The couple broke up before Ghenea turned 26. She was 24 years old.

15 Erin Heatherton

• Duration: 10 months
• When: 2012
• Ages: Erin 22, Leonardo 38

DiCaprio’s third relationship with a Victoria’s Secret model came about when he started dating Erin Heatherton. The duo met at the 2012 Victoria’s Secret fashion show in New York. They dated for a short time and a source told Us Weekly about their breakup, “They split a few weeks ago,” the insider said. “There’s no bad blood—they still care about each other a lot.” 

16 What Erin Heatherton Is Doing Now

• Current age: 32 years old
• Occupation: Model
• Relationship status: Single

After her breakup with DiCaprio, Heatherton briefly dated Australian musician Felix Bloxsom. She grabbed headlines when she broke her contract with Victoria’s Secret, citing unrealistic body standards. Heatherton revealed to Time’s Motto, “My last two Victoria’s Secret shows, I was told I had to lose weight,” she said. “I was really depressed because I was working so hard and I felt like my body was resisting me. And I got to a point where one night I got home from a workout and I remember staring at my food and thinking maybe I should just not eat.”

• The couple broke up before Heatherton turned 26. She was 22 years old.

17 Toni Garrn

• Duration: 18 months
• When: 2013-2014
• Ages: Toni 21, Leonardo 39

DiCaprio dated yet another model, Toni Garrn, in May 2013, but they split in 2014. According to Us Weekly, they broke up because he was spotted in a Miami nightclub partying with 20 women. They briefly reunited in 2017, but the relationship fizzled out. 

18 Where Toni Garrn Is Now

• Current age: 28 years old
• Occupation: Model and actress
• Relationship status: Married to actor Alex Pettyfer

Toni Garrn moved on from DiCaprio with Magic Mike star Alex Pettyfer. According to the Daily Mail, the couple was first linked when they attended an Elton John Oscar party in 2019. They married in an intimate ceremony in October 2020. The model posted a wedding pic to Instagram along with the caption, “Now you really get to call me wifey.”

• The couple broke up before Garrn turned 26. She was 21 years old.

19 Kelly Rohrbach

• Duration: A few months
• When: 2015-2016
• Ages: Kelly 25, Leonardo 41

It seems like DiCaprio was on the road to an engagement when he dated Sports Illustrated model Kelly Rohrbach. They dated at the end of 2015, but were broken up by 2016. A source told People about their split, “They are very friendly and it’s super amicable,” the insider said. “They are both so busy and he’s got a big movie coming out, and she’s one of the biggest supermodels in the world. There is no other person in the picture.”

What Kelly Rohrbach Is Up To Now

• Current age: 31 years old
• Occupation: Actress and model
• Relationship status: Married to Walmart heir Steuart Walton

Kelly Rohrbach broke into acting after her split with DiCaprio to play C. J. Parker in the film Baywatch. According to the Daily News, Rohrbach secretly married her Walmart heir boyfriend Steuart Walton in 2019 following a two-year romance.  

• The couple broke up before Rohrbach turned 26. She was 25 years old.

21 Never Over 25

• Number of relationships: 11
• Partner’s age: Between 18 and 25 years old

DiCaprio has had several romantic relationships in his life, and each of them ended before the woman turned 26. Clearly, there’s a weird pattern here!

• DiCaprio current age: 46 years old
• Morrone current age: 23 years old

DiCaprio and Morrone have been together since 2018, and they seem to be in perfect love. We even learned in December 2020 that the couple planned to move in together! Time will tell if Morrone will still be in DiCaprio’s life on June 16, 2023, on her 26th birthday!