Jake Gyllenhaal's Relationship Timeline Explained

Jake Gyllenhaal's public relationship history began with a redheaded singer named Jenny Lewis. Also an actor known for her roles in the movies "Foxfire" and "The Wizard," Lewis was the lead singer of the indie rock band Rilo Kiley. She and Gyllenhaal dated for a short time in 2001, according to People. One of the only photos of the couple shows them decked out in early 2000s outfits, pouting moodily and holding hands at the Hollywood "Donnie Darko" premiere. Their relationship was brief, and it's unclear when and why they ended things. Though their relationship was short-lived, the two have remained close over the years.

According to People, Gyllenhaal watched Lewis' set at Coachella in 2009 with his girlfriend at the time, Reese Witherspoon. It appears they all got along pretty well — later in 2009, Lewis hung out with Gyllenhaal and Witherspoon after one of her shows in Hollywood, per People, and in 2010, he was seen leaving a gym wearing a sweatshirt with Lewis' face on it. Their friendship even stirred up some drama when, in 2011, he took Lewis to the Golden Globes shortly after ending things with Taylor Swift (don't worry, we'll get to that whole situation later). Despite the rumors, Gyllenhaal and Lewis just seem to be lifelong pals.

"Black Swan" actress Natalie Portman was first linked to Jake Gyllenhaal in 2002, according to E! News, but the two didn't make headlines until 2006. As usual, Gyllenhaal kept details of their relationship private, and the two reportedly only dated for a few months in 2006. However, it seems like they were able to stay friends after things ended, as they starred in the 2009 film "Brothers" together (via E! News).

In 2011, while presenting Portman with a Desert Palm Achievement Award for her performance in "Black Swan," (via Us Weekly), Gyllenhaal revealed that the two first met at a Star Wars convention, saying, "[I was] waiting in line for her to sign my Queen Amadala doll and I'm really hoping she wins the Oscar. Because if she does, then that doll is going to be worth a s***oad of money!" All jokes aside, Gyllenhaal seemed keen to convey his admiration for the actress despite their fizzled romance, calling her the "Audrey Hepburn of our generation" and adding that she is "graceful, has amazing eyebrows, and is talented, really short, funny, smart, dedicated, incredibly kind, and Jewish!"

Photos from Jake Gyllenhaal and Taylor Swift's relationship make it seem straight out of a Hallmark movie — all smiles and hugs and drinking lattes on a scenic street. But however cute their relationship looked, it didn't last long — the two were first spotted together in October 2010, and by January 2011 they had broken up. According to Us Weekly, Gyllenhaal told Swift that it "just wasn't working out," and Swift was upset and felt "burned" by him.

Swift dealt with the breakup in a way many musicians do: by writing a song about her heartbreak. Two years later, she released her album, "Red," with a song on it called "All Too Well," which chronicled their up-and-down relationship. It included lyrics like, "And you call me up again just to break me like a promise / So casually cruel in the name of being honest." For such a private guy like Gyllenhaal, an ex-girlfriend writing a hit song (and possibly multiple songs) about you has to be a bit upsetting. But according to Swift, he took the situation all too well: Taylor told New York Magazine (via Us Weekly), "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."

Anna Kendrick is known for being one of Hollywood's favorite lovably awkward stars — but should she also be known as one of Jake Gyllenhaal's ex-girlfriends?

There's no solid proof that the "Pitch Perfect" star dated Gyllenhaal, but it's certainly not out of the realm of possibility. The two were reportedly spotted cozying up to each other (per E! News) — and when they worked together on the police drama "End of Watch" in 2011, some speculated that they were more than just friends. Not only did their characters hook up on the show, but Kendrick also revealed to E! News that shooting with Jake was "incredibly intimate" due to the close quarters and small crew, and that "... Jake and I would be holding hands and suddenly we'd be like, 'Oh, we're not filming.'" 

Whether their intimacy was just for the big screen or not, Kendrick seemed to have a bit of a crush. When the E! News interviewer asked her "how steamy" her relationship was with Gyllenhaal, she said, "Oh my goodness — I'm actually blushing. Yeah, it gets all sexy time with us." To be fair, we would be blushing, too.

In 2013, Us Weekly revealed that Jake Gyllenhaal was dating Emily DiDonato, a successful model who has been featured in Vogue and Sports Illustrated, and who was the face of Maybelline. Apparently, the two met in a spin class that Gyllenhaal frequented in Manhattan, and according to Us Weekly, they dated for a few months.

However, there aren't many photos of DiDonato and Gyllenhaal together, and neither of them ever confirmed they were in a relationship, so it's likely that whatever they had going on was pretty casual. Additionally, Gyllenhaal was 32 at the time while DiDonato was 22, so the 10-year age gap may have prevented them from connecting in a meaningful way — although it appears he tends to date younger women. It also appears that the same year he was supposedly dating DiDonato, he began dating Alyssa Miller, with whom he was definitely in a relationship, so it's hard to say whether he and DiDonato were ever seriously involved.

Ruth Wilson, an English actress known for her roles in "Luther" and "Jane Eyre," was linked to Jake Gyllenhaal in December 2015 after they were seen arm-in-arm after a dinner date, per E! News. Then, in May 2015, they were spotted in a workout class together (seriously, the man loves picking up women at the gym), where they were seen kissing after the class.

Despite the canoodling, Wilson did not confirm their relationship when she was asked about it. According to The Edit, via E! News, she and Gyllenhaal became close while they worked together on the Broadway production "Constellations," but Wilson didn't imply that it was a romantic connection: "We've become like brother and sister a little bit," she said. Whether it was romantic or platonic, she had nothing but good things to say about Gyllenhaal, telling The Edit, "He's adorable, a really good guy. ... I trust him implicitly."

French model Jeanne Cadieu has held Gyllenhaal's heart since late 2018, according to People. The couple has been occasionally spotted on walks in Paris and New York, but overall they have kept their relationship very private.

So private, in fact, that their first joint red-carpet event wasn't until 2021, when the pair showed up to support Gyllenhaal's sister, Maggie, at the premiere of her movie, "The Lost Daughter." Gyllenhaal didn't intend to walk the red carpet with Cadieu, but Maggie made it happen. "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. And to be there to support my sister was what we're there to do, and I was like, 'Oh yeah, this is family,'" Gyllenhaal said on "The Howard Stern Show" (via People).

According to People, the couple quarantined together, and Gyllenhaal even made Cadieu a loaf of sourdough bread each day to deal with quarantine boredom. It seems like he may have found with Cadieu what he hasn't been able to find in the past — someone to really settle down with. Gyllenhaal opened up about his relationship (a very rare thing for him) to Esquire, saying, "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."