BEFORE he started dating Jeanne Cadieu, Jake Gyllenhaal was romantically linked to Taylor Swift and Rachel McAdams.
Previously, the Oscar nominee was also in relationships with Kirsten Dunst and Reese Witherspoon.
Who has Jake Gyllenhaal dated?
Jenny Lewis
In 2001, Jake Gyllenhaal was dating singer-songwriter Jenny Lewis.
Although Jake and Jenny’s relationship was short-lived, the pair have remained friends.
Throughout the years, the former couple has shown support for each other’s work.
In 2011, Jake even brought Jenny as his date to the 68th Golden Globes ceremony.
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Kirsten Dunst
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In 2002, Jake started dating Kirsten Dunst.
They were introduced to each other by the former’s sister, Maggie Gyllenhaal.
Kirsten and Maggie were co-stars in the 2003 drama, Mona Lisa Smile.
Jake and Kirsten moved in together and adopted a German Shepherd named Atticus, their dog died in 2015.
In July 2004, the couple called it quits and went their separate ways.
At the time, a rep for Jake told People: “Kirsten and Jake remain the best of friends.
“Details regarding when and why their romantic relationship stopped are not being provided, but suffice it to say it happened some time ago. They are still very close.”
Natalie Portman
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Jake was first romantically linked to Natalie Portman in 2002.
Following the former’s split from Kirsten, he was spotted on a few dates with the Star Wars alum in 2006.
Eventually, the Jake and Natalie dating rumors fizzled out.
The two went on to star in the 2009 drama, Brothers.
Reese Witherspoon
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Between March 2007 and December 2009, Jake had an on-off relationship with Reese Witherspoon.
Regarding their split, there was speculation that Jake wanted to marry Reese, but she wasn’t ready to tie the knot.
An insider told Us Weekly: “When it comes down to it, she [Reese] isn’t ready to get married and he [Jake] is.
“She felt pressured to wed again, but she wasn’t ready.
“She couldn’t give Jake enough and she got cold feet.
“From the beginning, Jake wanted all of her, and she knew he deserved someone who could give him that.
“He wanted to be together at all times, and it became a lot for her to juggle with work and the kids.”
While discussing his past romance with Reese, Jake said on The Jess Cagle Interview: “She is, as I would say about most of the women who I’m close friends with or had relationships in my life, one of the smartest, strongest, people I’ve ever met.
Taylor Swift
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In October 2010, Jake and Taylor Swift were first rumored to be dating when they were spotted backstage together during a Saturday Night Live taping.
Earlier that year, the Spider-Man alum and the Thank You Aimee singer first met during a dinner party at Gwyneth Paltrow and Chris Martin’s home in London.
By January 2011, it was revealed Jake and Taylor decided to split up.
A few songs from Taylor’s 2012 album Red are rumored to be about her relationship with Jake.
Specifically, her single All Too Well and its corresponding short-film and music video are speculated to be about their past romance.
Anna Kendrick
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After his split from Taylor, it was rumored that Jake moved on with Anna Kendrick.
In late 2011, Jake and Anna were seen together on a few occasions.
At the time, the pair were co-starring in the 2012 thriller, End of Watch.
However, the romantic speculation about the Tony nominee and the Pitch Perfect actress was never confirmed.
Alyssa Miller
Model Alyssa Miller began dating Jake in 2013
They were first rumored to be dating after being snapped snogging in a New York City coffee shop.
But their fling was short-lived and reportedly fizzled out within a year.
Rachel McAdams
Back in 2014, rumors swirled that Mean Girls star Rachel McAdams was dating Jake.
At the time, the pair were filming the sports drama Southpaw.
They were pictured going for cozy dinners and even attended boxing matches together.
But they both denied rumors about them dating and insisted they were just good friends.
Ruth Wilson
After dismissing rumors about dating Rachel, Jake was linked to actress Ruth Wilson.
He was caught kissing her in 2015 after a workout class in NYC.
They were working on Broadway show Constellations at the time, but never confirmed dating rumors.
Jeanne Cadieu
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Since 2018, Jake has been loved up with Jeanne Cadieu.
He has a 16-year age difference with model Jeanne, but the pair have been together almost three years.
They were first photographed together in Paris in December 2018.
Speaking to Vogue in May 2020, he said: “Seeing life as something that is, you know, fleeting, and the world being as it is now.
“I’ve turned to my family, I’ve turned to my friends and I’ve turned to love. I’m a little less interested in the work, I would say, and more interested in that.”
In February 2022, the actor told Esquire in another interview: “In a lot of ways, we’re family. I’m in a relationship that is full of love and support. I feel so at ease.”
“I’m not unaware that there’s interest in my life. My life is wonderful.”
The star added about his model significant other: “I have a relationship that is truly wonderful, and I have a family I love so much. And this whole period of time has made me realize that.”
On March 20, 2022, Jake and Jeanne stepped out together for the red carpet premiere of the actor’s film, Ambulance.
This was their first appearance together since they attended the release of Maggie Gyllenhaal’s motion picture, The Lost Daughter, in September 2021.