Who's Dated Who

Who is Jake Gyllenhaal Dating​​

The Brokeback Mountain star has had his fair share of high-profile partnerships throughout the years. Before dating Taylor Swift for three months in 2010, he was linked to Reese Witherspoon and Kirsten Dunst. The whirlwind affair is said to have inspired the Grammy winner’s fourth album, Red, and its heartbreaking breakup song “All Too Well.”

Though the Southpaw star keeps his personal life private, he has publicly expressed his wish to establish a family eventually.

Who is Jake Gyllenhaal Dating now?

It’s a low-key type of love! Jake Gyllenhaal and Jeanne Cadieu’s romance has been under wraps — but it appears to be continuing strong. The couple’s relationship was verified by news sources back in December 2018 after they were photographed vacationing together in London and Greece that summer. While their 16-year age gap may have piqued the interest of some people, the two remained unfazed. “Jeanne is exceptionally mature for her age.” “She’s quirky, brilliant, and enjoys history and literature; she’s a very fantastic and well-rounded person,” a source said. “She and Jake took things slowly at first, but they’re now really serious.”

The reclusive pair has only made a few public appearances together — and has primarily kept their courtship off of social media. Gyllenhaal shared some insight into his approach to dating in the spotlight before falling for the French beauty.

“I believe that when you’re in a relationship, you’re continuously inspected, as are your friends, but… “I’d prefer not to discuss my personal life,” he told news outlets back in 2017.

Recently

In 2021, Cadieu and her beau were photographed separately on the red carpet at New York City’s 74th annual Tony Awards. The California native was nominated for Best Actor in a Leading Role in a Play for his work in Sea Wall/A Life but lost to Andrew Burnap from The Inheritance. The pair made their red-carpet debut at the New York Film Festival two days later. On September 28, the two attended the New York Film Festival premiere of Maggie Gyllenhaal’s directorial debut, The Lost Daughter. The couple stood for photographs with their arms around one other before joining The Guilty actor’s older sister and her husband, Peter Sarsgaard, for a few group images.

Gyllenhaal was present to support his sister and “was thrilled to have his fiancée at his side,” an eyewitness told Us exclusively. “They appeared to be comfortable together. For picture ops, he placed his arm around her. She appears to get along well with Maggie and Peter, as if she’s already a member of the family.”

All in all, Jake is a pretty mysterious person, but his love life isn’t that under wraps. Read on to find out his dating history.

Jake Gyllenhaal Dating History

Natalie Portman

Jake was said to have dated Marvel actress Natalie Portman in 2006. The couple was seen out on a dinner date, but their romance did not last long. They co-starred in the 2009 film Brothers. Not sure if this was really a romance or a friendship that was taken out of context by the people.

Jenny Lewis

Back in 2001, Jake was 21 years old and dating singer-songwriter Jenny Lewis. Their relationship was brief since they were both just starting out in their careers. They stayed friends, and Jake even invited Jenny to the 2011 Golden Globes event.

Kirsten Dunst

Jake met Hollywood actress Kirsten Dunst while working on Mona Lisa Smile with his sister Maggie. They started dating in 2002 and eventually moved in together, acquiring a German Shepherd called Atticus. However, the couple broke up back in 2004, and Jake maintained possession of their dog, who died in 2015. Kirsten explained to the News of the World that they split up due to a difference in lifestyle preferences. “He’s a stay-at-home boy, and I’m an out-on-the-town gal,” she had explained.

Reese Witherspoon

Jake had an on-again, off-again romance with Legally Blonde actress Reese Witherspoon between March 2007 and December 2009. When Reese and Jake met, she was in the midst of her divorce from Ryan Phillippe. She is now happily married to talent agent Jim Toth.

The couple broke up for a final time in 2009, yet they remain close friends. Jake expressed his adoration for Reese in a 2016 edition of The Jess Cagle Interview. “She is, as I would say about most of the women with whom I’ve had close friendships or interactions in my life, one of the brightest, strongest individuals I’ve ever known,” he remarked.

Taylor Swift

Taylor Swift and Jake allegedly met during a dinner party hosted at Gwyneth Paltrow’s London house, which she shared with then-husband Chris Martin, in 2010. They were later seen backstage at a Saturday Night Live taping in October 2010. Taylor and Jake allegedly split early in 2011 after spending the holidays apart. Nothing is really known about this couple. Just the fact that songs were written here and there!

Following the publication of Taylor Swift’s 2021 ‘Red’ album, Jake became popular since many Swifties believe her song, All Too Well, which was turned into a 10-minute short video, is about their prior romance.

Anna Kendrick

Anna Kendrick, the Pitch Perfect star, is another actress Jake is said to have dated. In 2011, the couple worked together on the action thriller film End of Watch.

However, the rumours were never proven.

Alyssa Miller

Jake and model Alyssa Miller began dating in 2013. They were originally linked after being photographed being intimate in a New York City coffee shop. Their romance, however, was short-lived and apparently ended within a year.

Rachel McAdams

Mean Girls actress Rachel McAdams was said to be dating Jake back in 2014. The couple was filming the sports drama Southpaw at the time. They were seen having intimate dinners together and even attending boxing fights together. However, they both refuted reports of them dating and stated that they were only good friends.

Ruth Wilson

Jake was linked to actress Ruth Wilson after he denied dating Rachel. In 2015, he was seen kissing her after an exercise session in New York City. They were both working on the Broadway play Constellations at the time, but they never acknowledged their relationship.