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.Photo:Carmen Valdes/Ron Galella Collection/Getty ; Rich Fury/VF22/Getty

Carmen Valdes/Ron Galella Collection/Getty ; Rich Fury/VF22/Getty
Jake Gyllenhaalhas dated his share of famous ladies.
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, theBrokeback Mountainstar opened up on SiriusXM’sThe Howard Stern Showabout 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 hostHoward 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.”
Here’s a look back at Jake Gyllenhaal’s dating history.
Kirsten Dunst
Jake Gyllenhaal and Kirsten Dunst at the The Shrine Auditorium in Los Angeles, California.Jeff Vespa/WireImage

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

Kevin Mazur/VF/WireImage
Gyllenhaal and Witherspoon met on the set of the 2007 filmRenditionand 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 divorcedRyan Phillippe, toldVogueof 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 toldInStylein 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 ofThe Jess Cagle Interview.
Taylor Swift
Taylor Swift, Jake Gyllenhaal.Michael Buckner/WireImage // Jason Merritt/Getty

Gyllenhaal’s romance withTaylor Swiftmayhave 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 albumRed, including “All Too Well” took inspiration from theDonnie Darkostar.
A 10-minute version of the breakup ballad, which appeared on Swift’s 2022 albumRed (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 actoraddressed the fan theoriesabout “All Too Well,” tellingEsquire, “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
Jake Gyllenhaal and Alyssa Miller are seen on August 26, 2013 in New York City.Ignat/Bauer-Griffin/GC Images

Ignat/Bauer-Griffin/GC Images
TheRoad Houseactor metSports Illustratedmodel 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 outbetween 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
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

Gisela Schober/Getty
Gyllenhaal was first linked to Cadieu, a French model, in late 2018 when they werespotted on walks togetherin New York City and Paris.
Until making theirfirst joint red carpet appearancein September 2021, the pair kept their relationship extremely private. They attended a screening ofThe Lost Daughterat the 2021 New York Film Festival, in support of Maggie Gyllenhaal’s directorial debut. According to the actor, Cadieu wasexcited to supporther 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’sThe 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 ofThe Innocentat the Cannes Film Festival in 2022 and a special screening of Gyllenhaal’s filmRoad Housein 2024.
In February 2022, theAmbulancestar spokewithEsquireabout 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.
source: people.com