Jake Gyllenhaal's Relationship Timeline Explained

Jacob Benjamin Gyllenhaal, professionally known as Jake Gyllenhaal, is one of the most prolific actors of his time, thanks to movies like "Brokeback Mountain" and "Jar Head," per IMDb. He is one of Hollywood's leading heartthrobs, but he has kept the details of his love life largely under wraps.

Thanks to Biography, we know that Gyllenhaal was nominated for an Academy Award for best supporting actor and won the Golden Lion at the Venice Film Festival thanks to his portrayal of a love-sick cowboy, starring opposite Heath Ledger. The last fans saw the actor was in 2019, when he joined the Marvel Universe Mysterio in "Spider-Man: Far From Home." But let's be honest, fans want to know more about his personal history.

Gyllenhaal has dated his fair share of women, from Taylor Swift to Kirsten Dunst, per Us Weekly. Read on to learn more about who he has been linked to in past relationships.

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.

When you think about Jake Gyllenhaal and Kirsten Dunst, it's almost guaranteed that the first thing you picture is that iconic photo of Dunst eating a salad with her hands as Gyllenhaal stares at her in either abject horror or utter boredom — it's impossible to tell. The bewildering photo may actually be a good representation of their relationship — after their breakup, Dunst revealed that they were very different people: "He's a stay-at-home boy and I'm an out-on-the-town girl," she told News of the World (via InStyle).

Though the relationship wasn't meant to be, it seemed to be fun while it lasted. After the two were set up by Gyllenhaal's sister, Maggie, in 2002, they got serious, moving in together and even adopting a cute pup named Atticus, according to InStyle. But ultimately, the early 2000s "it" couple couldn't make things work, possibly due to commitment issues. Dunst told People just two months before their breakup, "Oh, I'm too young to get married. ... Seriously, I'm 22 years old." The two broke up in 2004, and unfortunately, they didn't appear to stay too close after the breakup. As Dunst told Allure via Us Weekly in 2009, "It would be nice to see him, but we're not good friends."

"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!"

Looking at Reese Witherspoon and Jake Gyllenhaal's relationship, it's clear that there were some issues from the start. The two first met in 2006, per People, and became friends — with a bit of a crush on one another. Over the next few months, the two got close, but by the summer of 2007, Witherspoon decided to take some space. A source told People, "They broke up. It's totally and completely over. Reese was the one who had to do it. She just got out of a divorce and was so concerned with her family, she just didn't have the time for him and he really demanded that."

But later that year, the two were officially dating, with Witherspoon referring to Gyllenhaal as "a really fantastic guy." She told Vogue (via People), "He's very supportive. Suffice it to say, I'm very happy in life ..." While Gyllenhaal was his usual private self in regard to the relationship, a source who knew the couple told People, "Jake finds it attractive that she's such a great mom. He really loves kids and wants a family." However, this "family man" vibe that Gyllenhaal was exuding seems to have been part of why the two eventually broke up in 2009. According to Us Weekly, Gyllenhaal was ready to get married and settle down, but Witherspoon was still healing from her prior divorce and wasn't ready for wedding bells yet.

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."

After Jake Gyllenhaal's high-profile and dramatic split with Taylor Swift, all eyes were on him — and any dates he dared to take out. In April 2011, just a few months after his breakup with Swift, he was spotted with Jessica Lowndes, an actress known for her roles in Hallmark movies as well as "90210" and "The Haunting of Molly Hartley."

The two were reportedly grabbing breakfast together at New York City's Greenwich Hotel, per MTV. And according to Glamour, the pair then attended a party together later that evening, with a witness telling the outlet they looked "very friendly." But when it comes down to it, going on a date or two isn't the same as officially dating someone, and Gyllenhaal's representative later told E! News that Gyllenhaal and Lowndes were not together. Lowndes' representative, on the other hand, simply said "no comment" when asked if she and Gyllenhaal were dating, so it's hard to say for sure what was going on between those two.

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.

Minka Kelly is an actress and model best known for her roles in "Friday Night Lights" and "Parenthood." It seems she and Jake Gyllenhaal had a spark back in 2012 when the two went on a few dates, per E! News, but neither confirmed that they were dating. Then, in 2014, the two actors were reportedly seeing each other again — a source told Us Weekly (via E! News) that the two "hook up whenever they're single." E! News speculated that distance was part of what prevented them from becoming official, since Kelly spent a lot of time filming "Almost Human" in Vancouver while Gyllenhaal lived in New York City.

Whether or not Kelly and Gyllenhaal were ever an official item, he isn't the first big-name actor she's dated. In the past, she has been involved with Chris Evans, John Mayer, Brian White, and Trevor Noah, according to PopSugar.

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.

You know how Jake Gyllenhaal met his possible fling, Emily DiDonato, at the gym? Well, that strategy seems to work well for him, because that's also where he met his next girlfriend, Alyssa Miller (who is also, coincidentally, a Sports Illustrated model like DiDonato), according to Us Weekly.

Alyssa Miller and Jake Gyllenhaal met at the gym in 2013, and the couple dated for six months, per Us Weekly. They both seemed happy, and Miller told Us Weekly a few months into the relationship that things were "good" and that they enjoyed their time together, frequently having dinner parties and cooking. But it seemed like Gyllenhaal's busy and demanding work schedule was the culprit for their split, with a source telling Us Weekly, "Things were really good between Jake and Alyssa right up until he had to leave for LA to go shoot a movie [Nightcrawler] in the fall. Then the distance just really got to them."

Jake was also filming "Southpaw" at the time, a movie in which he played a boxer. The director of the movie, Antoine Fuqua, said (per NY Daily News), "Literally, I think he broke up with his girlfriend because he was just in the gym every day." Ouch.

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."

Rachel McAdams, most famously known for starring in "The Notebook," was working with Jake Gyllenhaal in "Southpaw" in 2014 when rumors began flying about the pair being more than friends. They were spotted going out together multiple times, according to Bustle, and the fact that they play a married couple in "Southpaw" didn't help to dispel rumors.

An insider told OK! Magazine, "There is no denying the electric chemistry between Jake and Rachel. The attraction was instant. From the moment they started working together, Jake and Rachel just connected intellectually and emotionally." A witness who saw the two dining together during the summer of 2014 echoed the sentiment, saying (per OK! Magazine): "They looked really happy and were very friendly." Despite the signs of romance, both parties brushed off rumors that they were together; in fact, when McAdams was asked if she was involved with Gyllenhaal, she laughed and said, "Oh, no" (per Bustle).

Whether or not they were an item, Gyllenhaal clearly admired McAdams, telling Marie Claire, "She [Rachel] has that beautiful darkness but exudes a real, true light. To be dark and light at the same time is as rare as it is infectious." An incredibly (...suspiciously?) endearing thing to say about someone, if you ask us!

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."