The Huge Similarity Jake Gyllenhaal and Leonardo Di Caprio’s Dating Lives Share

Jake Gyllenhaal and Leonardo DiCaprio are often compared. Gyllenhaal, 38, is just a few years younger than 44-year-old DiCaprio. The two are serious actors that take on difficult, often physically taxing, roles.  They’ve both been nominated for Oscars — DiCaprio has one to his name for his work on The Revenant.  

A lot of fans think that Gyllenhaal is following in DiCaprio’s footsteps: They see both men as dedicated actors with a love for the craft. There’s something else these two may have in common — they have similar tastes in dating.

Leonardi Di Caprio appears to only dates women 25 or under

Leonardo DiCaprio
Leonardo DiCaprio | Frazer Harrison/Getty Images

DiCaprio may be in his mid-40s, but he has never publicly dated a woman over 25. He also usually dates models. 

The Titanic star has only dated two non-models as far as we know. He dated actress Blake Lively briefly in 2011 when she was 23 and he was 36. He also had a fling with Kelly Rohrbach in 2015, when she was 25. Technically she’s also a model, although she’s been in a few movies also.  

DiCaprio is currently dating Camila Morrone, who is a 22-year-old model.  They’ve been together for 2 years, which means they started dating when she was 20. The couple keeps quiet about their relationship, although some sources say it’s getting serious. Morrone could be the one that lasts past the age of 25.  

Jake Gyllenhaal has been seen around town with a lot of younger ladies

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Gyllenhaal is also often seen with younger women. He’s currently dating Jeanne Cadieu, a 23-year-old model. Considering how similar his current relationship is to DiCaprio’s, fans wonder if he’s heading down the same path.  

Gyllenhaal has had a few well-publicized relationships with younger women. He dated Kirsten Dunst in 2001 when she was 20, but he was only 21 at the time. Taylor Swift was 21 when their relationship started, and Gyllenhaal was 29. In 2013, a 32-year-old Gyllenhaal had two trysts with younger women: He dated Emily DiDonato, a model who was 22 at the time, and Alyssa Miller, who was 24.

There are a few notable differences between Gyllenhaal’s dating life and DiCaprio’s. Gyllenhaal doesn’t just date models. Although he’s currently dating a model, and he has before, his past girlfriends include actresses and singers.  

Gyllenhaal doesn’t just date 25-year-old women either, and he’s dated a woman older than himself on more than one occasion. His first public relationship was with Jenny Lewis, who was 25. Gyllenhaal was 20 at the time. He also dated Reese Witherspoon in 2007: She was 31 at the time and he was 26. 

Jake Gyllenhaal doesn’t seem as committed to the rule as Leonardi Di Caprio

Gyllenhaal has dated women older than 25 in the past. DiCaprio has not. It would seem that for Jake, he tends towards dating younger women, but he’s not afraid of having a girlfriend over 25. He’s even dated women older than him on a few occasions.  

DiCaprio has never dated a woman over 25 years old that we know of, and he’s never dated anyone older than he was at the time. Even in his early career, he dated Gisele when she was 18 and he was 24.  

It remains to be seen if Gyllenhaal will truly follow DiCaprio’s dating footsteps. His history suggests that he’s more open to dating women of various ages and career paths than DiCaprio.