Meet Jake Gyllenhaal’s Girlfriend & Look Back at Who Else He Dated Before And After Taylor Swift

Jeanne Cadieu (2018 – Now)

Jake Gyllenhaal is currently dating French model Jeanne Cadieu. The pair were first romantically linked in 2018 when they were spotted on walks together in New York City and Paris. The couple attended their first red carpet together at the September 2021 premiere of The Lost Daughter, a film directed by his sister, Maggie Gyllenhaal.

The actor told Esquire in 2022 that he grew closer to Cadieu during the COVID pandemic. “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. He later added, “I’m not unaware that there’s interest in my life. My life is wonderful. 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.”

Cadieu is currently a student at Columbia University (where Jake and Maggie were former students), per her Instagram bio. She’s a successful model signed with Elite Model Management NYC and Women Management Paris and has walked for brands like Stella McCartney, Valentino, Saint Laurent, and The Row.

In September 2023, Gyllenhaal told People that his relationship continues to be “wonderful” with Cadieu. “We are private, but I guess we are who we are. We’re just living our lives. We always have. And I love that people are interested, but at the same time, it’s like what’s ours is ours.”

The 43-year-old actor revealed that he’s open to the possibility of marriage with Cadieu. “I love her so much; she’s such a good person,” he said on The Howard Stern Show in October 2021, according to People. On the talk show, he added that marriage is “a choice for both of us.”

Alyssa Miller (2013 – 2014)

The actor was briefly linked to Sports Illustrated model Alyssa Miller for at least six months in 2013. Rumors started swirling after they were photographed on a PDA-filled bike ride in NYC during the summer of 2013.

“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.”

It appears as though their relationship didn’t last long. A source confirmed to the entertainment site that Gyllenhaal and Miller called it quits after just six months of dating. They may have gotten back together for a short period in May 2014 after they reunited for a stroll in NYC.

Taylor Swift (2010)

Swifties know Jake Gyllenhaal as the singer’s ex who inspired her single “All Too Well,” which got a 10-minute re-release on Red (Taylor’s Version). The former lovebirds were set up by actress Gwyneth Paltrow. In December 2010, Paltrow said in an interview with USA Today that she played matchmaker between Swift and Gyllenhaal, who met at a dinner party at the London home Paltrow she shared with her then-husband Chris Martin.

“I’ve just known Jake for a long time, and he’s a great guy,” she said, “and Chris has a friendship with Taylor.” She continued, “It’s so weird. I wonder how people find out these things. It was a while ago, so I don’t know why it would come out today.”

The pop star and the actor were first spotted together at a Saturday Night Live taping in October 2023. Throughout the fall, they enjoyed a few autumnal coffee dates and strolls around Brooklyn near Jake’s sister’s home. People reported that they ordered specialty maple lattes. However, when the holidays came around, it appeared that the couple called things off. “They’re over,” a source told People about the brief relationship. “It ended last month.”

Reese Witherspoon (2007 – 2009)

Gyllenhaal and Witherspoon first met on the set of Rendition (2007) and began dating shortly after. In her Vogue November 2008 cover story, Witherspoon said the actor was “very supportive.” She added, “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.”

The couple even traveled abroad together and spent weekends outside of L.A., including in Ojai, where the mother-of-two had a farmhouse at the time. “We have chickens and we grow cucumbers and tomatoes. I love it. It reminds me of where I grew up in Tennessee,” she told InStyle in October 2009, per People.

One month later, a source close to the Legally Blonde star told People that the couple had parted ways. Years later, Gyllenhaal explained that there were no hard feelings between the exes. “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 during an episode of The Jess Cagle Interview in 2016.

Kirsten Dunst (2002 – 2004)

Dunst and Gyllenhaal started seeing each other romantically in 2002 after they were introduced by the actor’s sister, Maggie Gyllenhaal, who starred in Mona Lisa Smile (2003) with the Spider-Man actress. When they met, he was only 22 years old, while Dunst was 20.

The young couple’s relationship progressed quickly; they moved in together and adopted a German Shepherd named Atticus (Gyllenhaal had the dog until it passed away in 2015). At the time, Dunst said in an interview with People that she was “too young” to get married to Gyllenhaal. “Seriously, I’m 22 years old. It’s so annoying that they put pressure on you,” she said two months before their breakup.

Their relationship came to an end in July 2004. “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.