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Jake Gyllenhaal’s Dating History: From Kirsten Dunst to Jeanne Cadieu

The 'Road House' actor has been dating French model Jeanne Cadieu since 2018

<p>Carmen Valdes/Ron Galella Collection/Getty ; Rich Fury/VF22/Getty</p> Kirsten Dunst and Jake Gyllenhaal at the Metropolitan Museum of Art in New York City, New York. ; Jake Gyllenhaal and Jeanne Cadieu attend the 2022 Vanity Fair Oscar Party on March 27, 2022 in Beverly Hills, California.

Carmen Valdes/Ron Galella Collection/Getty ; Rich Fury/VF22/Getty

Kirsten Dunst and Jake Gyllenhaal at the Metropolitan Museum of Art in New York City, New York. ; Jake Gyllenhaal and Jeanne Cadieu attend the 2022 Vanity Fair Oscar Party on March 27, 2022 in Beverly Hills, California.

Jake Gyllenhaal has dated his share of famous ladies.

From costars to singers and even setups by his sister, the actor has been linked to a few Hollywood stars, including Reese Witherspoon and Kirsten Dunst.

Most recently, the actor has been dating French model Jeanne Cadieu since 2018. After being spotted together in Paris that year, they made their red carpet debut in 2021, though have kept their long-term relationship fairly private.

In October 2021, the Brokeback Mountain star opened up on SiriusXM's The Howard Stern Show about the idea of settling down.

"That's all I want is to be a good husband and a father ... That really is what I want," he told host Howard Stern. "And now that I have fulfilled a lot of things in my career that I feel comfortable with, I can safely say that. I don't know if I could have said that before."

"I love her so much. She's such a good person," Gyllenhaal added of his girlfriend Cadieu, explaining that marriage is "a choice for both of us."

Related: Who Is Jake Gyllenhaal's Girlfriend? All About Jeanne Cadieu

Here's a look back at Jake Gyllenhaal's dating history.

Kirsten Dunst

<p>Jeff Vespa/WireImage</p> Jake Gyllenhaal and Kirsten Dunst at the The Shrine Auditorium in Los Angeles, California.

Jeff Vespa/WireImage

Jake Gyllenhaal and Kirsten Dunst at the The Shrine Auditorium in Los Angeles, California.

Dunst and Gyllenhaal began dating in September 2002 after being introduced by the actor’s sister, Maggie Gyllenhaal, who had starred in Mona Lisa Smile with Dunst.

Things moved quickly for the young couple, who moved into a $1.7 million Los Angeles home together and even adopted a German Shepherd puppy, Atticus.

By July 2004, however, the two had called it quits. “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," Gyllenhaal’s rep Stephen Huvane told PEOPLE.

Gyllenhaal kept their dog after the breakup, who died in 2015.

Reese Witherspoon

<p>Kevin Mazur/VF/WireImage</p> Jake Gyllenhaal and Reese Witherspoon attends the 2009 Vanity Fair Oscar party on February 22, 2009 in West Hollywood, California.

Kevin Mazur/VF/WireImage

Jake Gyllenhaal and Reese Witherspoon attends the 2009 Vanity Fair Oscar party on February 22, 2009 in West Hollywood, California.

Gyllenhaal and Witherspoon met on the set of the 2007 film Rendition and soon began dating. The couple even took their romance abroad in the summer of 2008 with visits to Paris and Marrakech.

“He’s very supportive,” Witherspoon, who had recently divorced Ryan Phillippe, told Vogue of Gyllenhaal for her November 2008 cover story.

“Suffice it to say, I’m very happy in life, and I’m very lucky to have a lot of really supportive people around me who care very much for me, and, you know, that’s all you can hope for in life. I am very blessed in that way,” she added.

Though they enjoyed visits abroad together, things were just as comfortable closer to home, the mother of two told InStyle in October 2009: “We spend the weekends outside L.A., in Ojai, where I have a farmhouse. We have chickens and we grow cucumbers and tomatoes. I love it. It reminds me of where I grew up in Tennessee.”

But just a month later, a source close to the actress told PEOPLE that the couple had parted ways. Despite calling it quits, Gyllenhaal made it clear years later that there were no hard feelings between them.

“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,” the actor said on a 2016 episode of The Jess Cagle Interview.

Taylor Swift

Michael Buckner/WireImage // Jason Merritt/Getty Taylor Swift, Jake Gyllenhaal
Michael Buckner/WireImage // Jason Merritt/Getty Taylor Swift, Jake Gyllenhaal

Gyllenhaal’s romance with Taylor Swift may have been brief, but it’s one that Swifties have continued to dissect years later.

The pair first made headlines in 2010 when they were spotted together in New York City. Their romance heated up in the following months and they were famously photographed enjoying a walk on Thanksgiving together.

However, their split was confirmed at the end of the year after they spent their December birthdays and the holiday season apart.

Neither Swift nor Gyllenhaal has publicly discussed their relationship, but fans of Swift speculated that a number of the songs on her 2012 album Red, including "All Too Well" took inspiration from the Donnie Darko star.

A 10-minute version of the breakup ballad, which appeared on Swift's 2022 album Red (Taylor's Version), further fueled speculation about the song's inspiration.

In the tune, Swift sings about a man who blamed a breakup on their age difference (Gyllenhaal is nine years older than Swift): "You said if we had been closer in age / Maybe it would have been fine / And that made me want to die."

In February 2022, the actor addressed the fan theories about “All Too Well,” telling Esquire, "It has nothing to do with me. It's about her relationship with her fans. It is her expression. Artists tap into personal experiences for inspiration, and I don't begrudge anyone that."

Alyssa Miller

<p>Ignat/Bauer-Griffin/GC Images</p> Jake Gyllenhaal and Alyssa Miller are seen on August 26, 2013 in New York City.

Ignat/Bauer-Griffin/GC Images

Jake Gyllenhaal and Alyssa Miller are seen on August 26, 2013 in New York City.

The Road House actor met Sports Illustrated model Alyssa Miller at the gym in New York City in the summer of 2013. They were later seen enjoying a smooch-filled bike ride through the city.

“You could tell they were a couple. There was lots of PDA going on,” an onlooker told PEOPLE at the time. “They didn’t make out, but they would kiss each other on the lips multiple times. More like little pecks and they were very touchy-feely. They couldn’t keep their hands off of each other.”

But despite their PDA, things fizzled out between the two after just six months, a source confirmed to PEOPLE. In May 2014, rumors of reconciliation arose after they were spotted enjoying another stroll in N.Y.C.’s Tribeca neighborhood.

Jeanne Cadieu

<p>Gisela Schober/Getty</p> Jeanne Cadieu and Jake Gyllenhaal attend the 75th Anniversary celebration screening of "The Innocent (L'Innocent)" during the 75th annual Cannes film festival on May 24, 2022 in Cannes, France.

Gisela Schober/Getty

Jeanne Cadieu and Jake Gyllenhaal attend the 75th Anniversary celebration screening of "The Innocent (L'Innocent)" during the 75th annual Cannes film festival on May 24, 2022 in Cannes, France.

Gyllenhaal was first linked to Cadieu, a French model, in late 2018 when they were spotted on walks together in New York City and Paris.

Until making their first joint red carpet appearance in September 2021, the pair kept their relationship extremely private. They attended a screening of The Lost Daughter at the 2021 New York Film Festival, in support of Maggie Gyllenhaal’s directorial debut. According to the actor, Cadieu was excited to support her boyfriend’s sister.

"My sister grabbed her, pulled her on that red carpet, which I think neither of us are really inclined to, you know, go on — even me," Gyllenhaal shared during an appearance on SiriusXM's The Howard Stern Show. "And to be there to support my sister was what we're there to do and I was like, 'Oh yeah, this is family.' "

The couple have walked plenty of red carpets together since, including a 75th-anniversary celebration screening of The Innocent at the Cannes Film Festival in 2022 and a special screening of Gyllenhaal's film Road House in 2024.

In February 2022, the Ambulance star spoke with Esquire about how the COVID-19 pandemic helped him and Cadieu grow even closer.

"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," he said.

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