You may know Jake Gyllenhaal as the prosecutor turned murder suspect in his latest Apple TV series Presumed Innocent — or as Taylor Swift‘s ex-boyfriend. Yes, we’re talking about the man who fans think the songstress wrote the lyrics “I’ll get older, but your lovers stay my age” about.

Jake has been in the industry for some time now, and has starred in many classic movies. Which also means his love life has been in the public eye for all to judge. So, we’re breaking down his dating history below!  

The heartthrob first got his big break in 2001 when he starred in Donnie Darko. The hit psychological film was the first of many projects to solidify his role as one of Hollywood’s best thriller actors.

That same year was a popping time for the actor as he was also romantically linked to another big actress. Jenny Lewis, who appeared in films like Troop Beverly Hills and The Wizard, was reportedly in a relationship with Jake. Although their romance was brief, the two seemingly had no hard feelings as they’re still friends today.

Following his early 2000’s success, Jake went on to star in many well known films like Brokeback Mountain, The Day After Tomorrow, Zodiac, Prisoners, Nightcrawler and so much more.

While his movie career stayed constant, one aspect of his life did not — his relationships. Following his split from Jenny, Jake began a romance with Kirsten Dunst in 2002. The couple dated for two years and during that time, they shared a home in the Hollywood Hills and even bought a German Shepard.

Unfortunately, the pair called it quits in December 2004. After their relationship ended, Jake took a brief break with love up until 2006. At the time, the Nightcrawler actor was rumored to have dated Natalie Portman.

It seems whatever happened between the two didn’t stop them from continuing a friendship as they both later starred in a film together. In 2009, they were in the movie Brothers, alongside Tobey Maguire

Jake has quite an extensive dating history, and we’ve barely scratched the surface. Keep scrolling to see who else the actor has been linked with. 

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