Jake Gyllenhaal’s Dating History: All of His Ex-Girlfriends

While some of us remember Jake Gyllenhaal‘s dating history ~all too well~, others need a reminder! The Brokeback Mountain actor has dated several A-list women during his time in the spotlight, including Kirsten Dunst, Taylor Swift and more.

As of 2021, Jake is in a relationship with girlfriend Jeanne Cadieu. However, it’s his previous romance with Taylor that continues to make headlines. The Academy Award nominee and the “Tolerate It” artist dated from around October 2010 to January 2011.

Taylor immortalized their three-month relationship in a song titled “All Too Well” off her 2012 album Red. Later, in November 2021, the eleven-time Grammy Award winner released Red (Taylor’s Version), as well as a new 10-minute version of “All Too Well.”

“Jake is mortified that Taylor has targeted him in ‘All Too Well,'” a source exclusively revealed to Life & Style after the 10-minute version’s release. “He’s such a private person and goes out of his way to avoid drama, so having their three-month fling dragged up in the song and hearing people gossip about it is a hard pill for him to swallow.”

According to the insider, Jake “thought” Taylor “was over” their relationship. “It seems like anyone who has dated her can’t escape from their past.”

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After the album’s initial release, Taylor claimed Jake didn’t take issue with any of the music. “He was like, ‘I just listened to the album, and that was a really bittersweet experience for me. It was like going through a photo album.’ That was nice,” the West Reading, Pennsylvania, native, who has since moved on with boyfriend Joe Alwyn, told New York magazine in 2013.

“Nicer than, like, the ranting, crazy e-mails I got from this one dude. It’s a lot more mature way of looking at a love that was wonderful until it was terrible, and both people got hurt from it — but one of those people happened to be a songwriter,” Taylor added. “So, what are you going to do? Did you not Wikipedia me before you called me up [for a date]?”

Scroll through the gallery below to learn more about Jake Gyllenhaal’s complete dating history.

Kirsten Dunst

The Marie Antoinette actress and the South Paw star dated from 2002 to 2004. While dating, Kirsten and Jake moved in together and even adopted a dog. During the height of their relationship, they were considered one of young Hollywood’s “It” couples, but they handled being under a microscope well. “Kirsten and I know what’s real and what isn’t. We know what happens when you are both actors,” Jake said during an interview with People at the time.

In 2009, Kirsten told Allure she and Jake are amicable, but not close, saying, “It would be nice to see him, but we’re not good friends.”

Reese Witherspoon

Jake and the Legally Blonde actress were together on and off from 2007 to 2009. “He’s very supportive,” Reese told Vogue during a 2008 interview. “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.”

Taylor Swift

At the time of their romance, Taylor was 20 years old and Jake was 29 years old. She alludes to their age difference multiple times in All Too Well, and even suggests Jake has continued to date younger women with the lyric: “The punchline goes, ‘I’ll get older but your lovers stay my age.'”

Alyssa Miller

Jake dated the Sports Illustrated model in 2013. “Things are good,” she told Us Weekly of their romance in November of that year. “I have people over all the time, and we cook. He’s the teacher.”

Come January 2014, their relationship fizzled out. “Things were really good between Jake and Alyssa right up until he had to leave for L.A. to go shoot a movie in the fall,” a source revealed to Us Weekly at the time. “Then the distance just really got to them.”

Jeanne Cadieu

Jake and the model have been together since 2018. Although they’re a pretty low-key couple, he did mention their romance during a May 2020 interview with Vogue, saying things “turned to love” amid the coronavirus pandemic after “seeing life as something that is, you know, fleeting, and the world being as it is now.”

It seems the pair are still going strong as they were spotted attending the French Open together in June 2023.