Here are all of Leo's former flames, 25 years old and under, then and now.
Leo has had a three-decade-long career of questionable pairings. I'm including the major films he starred in during the relationships to help with the timeline.
In 1999, 24-year-old Leo (The Beach, The Aviator) started dating 18-year-old Brazilian fashion model Gisele Bündchen, a relationship that lasted five years.
Gisele is one of the world's most recognizable supermodels and Victoria's Secret Angels. Now the seasoned model is married to seven-time Super Bowl MVP Tom Brady.
In 2005, 20-year-old Israeli model Bar Refaeli started dating 30-year-old Leo (The Departed, Inception), and continued dating him until she turned 25.
Bar went on to host The X Factor Israel and the Eurovision Song Contest in 2019 and led several successful business ventures in Israel.
After his relationship with Bar ended, Blake Lively dated Leonardo (J. Edgar) for only one year, when he was 36 and she was 23 years old.
Now Blake is an accomplished actor starring in everything from The Sisterhood of the Traveling Pants franchise to the original Gossip Girl. Following her quick relationship with Leo, she married and had children with fellow actor Ryan Reynolds.
In 2012, American Victoria's Secret model Erin Heatherton dated 37-year-old Leonardo (Django Unchained) for a hot minute when she was only 22.
After the split, Erin continued to have an illustrious modeling career, being featured in Sports Illustrated swimsuit campaigns and international brand ambassadorships.
In 2013, 20-year-old fashion model and actor Antonia "Toni" Garrn started a two-year relationship with 38-year-old Leo (The Great Gatsby, The Wolf of Wall Street).
A seasoned fashion model, Toni started walking the runway for Calvin Klein when she was 15 years old. In 2020, she married British actor Alex Pettyfer (I Am Number Four).
After his split with Toni, a 40-year-old Leonardo (The Revenant) paired up with 25-year-old actor Kelly Rohrbach in 2015 for a brief encounter.
Kelly starred as C.J. Parker in the film adaptation of Baywatch, a TV role originated by Pamela Anderson. In 2019, she married Walmart heir Steuart Walton.
In 2016, 41-year-old Leo took time off from acting to produce documentaries and also dated 24-year-old Danish model Nina Agdal. That same year, he finally won his first Academy Award for Best Actor in a Leading Role, for The Revenant.
Nina was a sought-after model featured in worldwide campaigns, most notably the 50th anniversary cover of the Sports Illustrated swimsuit issue with Chrissy Teigen and Lily Aldridge.
Leo's recent relationship with 21-year-old American model and actor Camila Morrone ended in the summer of 2022 when he was 47 and she turned 25.
Camila has modeled for Vogue and acted in James Franco's film Bukowski and the 2018 A24 film Never Going Back.
What do you think about Leonardo DiCaprio's past relationships?
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