Hollywood star Jake Gyllenhaal rose to fame in the late '90s and early 2000s with roles in movies such as Homegrown and Donnie Darko. Since then, Jake has been a staple in the movie industry and over the years he has dated many equally as successful ladies.
Today’s list takes a look at just which women Jake Gyllenhaal has been linked to — from his definitely confirmed relationships to those that have just been brief rumors which most people have forgotten about. From Hollywood star, Reese Witherspoon over to musician Taylor Swift — keep on scrolling to find out just which famous ladies couldn’t say no to Jake's charm!
Updated on December 1, 2021, by Michael Chaar: Jake Gyllenhaal has been a Hollywood heartthrob since his start in the entertainment biz back in the 2000s. Despite his success on-screen, Jake has remained unmarried for the entirety of his career, however, his love life has been anything but boring. The actor's first major relationship was with Reese Witherspoon back in 2007. The duo dated for two years before Jake moved on with Taylor Swift in 2010. With Taylor's album, her version of course, being such a hot topic, Jake Gyllenhaal has been dragged back into the mix when it comes to the whole "scarf" debacle. Throughout time, the actor went from dating Rachel McAdams, Anna Kendrick, all the way to Ruth Wilson, however, it appears as if he might be locking down with current girlfriend, Jeanne Cadieu. The duo have been dating since 2018, and fans are certain that she might be "the one."
10 Reese Witherspoon Dated Jake From March 2007 Until December 2009
Kicking the list off is Hollywood star Reese Witherspoon who dated the famous actor from 2007 until 2009. Judging from what they said about each other after their breakup — it certainly seems as if Jake and Reese ended things on a good note as Jake only has words of praise for the Legally Blonde star who is currently happily married to talent agent Jim Toth.
9 Taylor Swift Dated Jake From May 2010 Until March 2011
Next on the list is musician Taylor Swift who dated Jake Gyllenhaal from 2010 until 2011. Fans will surely remember that the two stars were often spotted together in public but unfortunately — things didn’t work out for the two in the long run. Luckily, the queen of relatable lyrics ended up writing a bunch of songs about the famous Hollywood star — and some of them became major hits!
8 Rachel McAdams Was Linked To Jake In June 2014
Let’s move on to Mean Girls star Rachel McAdams who was rumored to have dated Jake Gyllenhaal back in 2014.
Of course, neither of the two stars ever confirmed it but at the time they were often spotted going to dinners and attending sports events together. However, the two were also filming the sports drama Southpaw so perhaps it was all a part of their research for the movie — who knows.
7 Kirsten Dunst Dated Jake From September 2002 Until December 2004
Another famous Hollywood star that Jake Gyllenhaal has dated is Kirsten Dunst. The two were together from 2002 until 2004 and many probably remember those iconic photos of the two eating in public. Unfortunately, things didn’t work out between them but they surely ended up running into each other in the industry after their break up because both went on to become major movie stars!
6 Natalie Portman Was Briefly Linked To Jake In 2006
It certainly seems as if Jake Gyllenhaal has been linked to quite a few famous actresses as Hollywood star Natalie Portman is the next one on our list. Natalie was linked to Jake in 2006 but only for a brief moment as it certainly seemed as if the two quickly realized that they’re not meant for each other.
5 Anna Kendrick Was Linked To Jake During The Shooting Of Their Movie 'End Of Watch' In 2011
Next on the list is actress Anna Kendrick who has also been rumored to have dated Jake Gyllenhaal. Both stars were in the action thriller movie End of Watch and it was rumored that during the movie's shooting in 2011 they were actually more than just good friends. As expected, neither of the two actors ever confirmed a relationship.
4 Jenny Lewis Dated Jake 20 Years Ago — Back In 2001
Let’s move on to one of Jake's first known relationships — that with singer-songwriter Jenny Lewis back in 2001.
At the time, both stars were still at the beginnings of their careers in the industry and some could even go as far as saying that at the time Jenny was actually more famous than Jake!
3 Alyssa Miller Dated Jake From June 2013 Until May 2014
Next to today’s list is model Alyssa Miller who dated the famous Hollywood star from 2013 until 2014. Together, the two were often spotted out and about but unfortunately — after almost a year of dating the couple ended things and decided to go their separate ways. However — judging from Jake's current girlfriend which we will get to soon — it definitely seems as if Jake slowly developed a thing for models.
2 Ruth Wilson Was Linked To Jake In The Spring Of 2015
Another actress that Jake Gyllenhaal has been linked to is Ruth Wilson. In 2005 rumors started circulating that the two actors who were starting together in the on Broadway play Constellations are actually more than just friends and while they have denied being anything more than close work colleague colleagues — they were reportedly seen kissing and holding hands at parties!
1 And Lastly — His Current Girl, Jeanne Cadieu Started Dating The Star In 2018
Wrapping the list up is Jake Gyllenhaal’s current girlfriend — model Jeanne Cadieu. The two have been dating since 2018 and it certainly seems as if their 16-year-age difference isn’t stopping them from being happy. As of right now, Jake and Jeanne have been together for three years — which certainly means that things are quite serious between them!