Jake Gyllenhaal Dating History: Here’s Look At His Dating History Over The Years!


Jake Gyllenhaal, whose real name is Jacob Benjamin Gyllenhaal, is one of the most active actors of his generation thanks to films like “Brokeback Mountain” and “Jar Head.” He is one of Hollywood’s top heartthrobs, yet he has mainly kept the specifics of his romantic relationships a secret.

We learned from Biography that Gyllenhaal’s portrayal of a love-sick cowboy, in which he starred opposite Heath Ledger, earned him a nomination for an Academy Award for best supporting actor and the Golden Lion at the Venice Film Festival. The actor’s most recent appearance for fans was in “Spider-Man: Far From Home,” when he played Mysterio from the Marvel Universe. But let’s face it, his followers would like to learn more about his personal background.

According to Us Weekly, Gyllenhaal has dated a variety of women, including Kirsten Dunst and Taylor Swift. Continue reading to discover more about the people he has dated in the past.

2001: Jenny Lewis

Jenny Lewis, a redheaded singer, was the first person with whom Jake Gyllenhaal had a public relationship. Lewis was the main vocalist of the indie music band Rilo Kiley and was also an actor best known for her roles in the films “Foxfire” and “The Wizard.” According to People, she and Gyllenhaal had a brief romantic relationship in 2001.

At the Hollywood “Donnie Darko” premiere, the couple can be seen holding hands and pouting in one of the few pictures of them together, dressed in early 2000s fashion. It is unknown when and why they ended their brief romance. Despite the fact that their romance was brief, the two have stayed close throughout the years.

According to People, Gyllenhaal and his then-girlfriend Reese Witherspoon attended Lewis’ Coachella performance in 2009. The fact that Lewis went out with Gyllenhaal and Witherspoon after one of her performances in Hollywood later in 2009 and that he was spotted leaving a gym in 2010 while wearing a hoodie with Lewis’ face on it suggests that they all got along well.

When he invited Lewis to the 2011 Golden Globes shortly after breaking up with Taylor Swift, their friendship even caused some controversy (don’t worry, we’ll cover the entire incident later). Despite the accusations, Lewis and Gyllenhaal just seem to be close friends.

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2002 – 2004: Kirsten Dunst

It’s almost a given that the first image that comes to mind when you think of Jake Gyllenhaal and Kirsten Dunst is the iconic photograph of Dunst eating a salad with her hands as Gyllenhaal looks on with either absolute boredom or utter abject dread. After their breakup, Dunst confessed that they were extremely different people: “He’s a stay-at-home boy and I’m an out-on-the-town lady,” she told News of the World. Therefore, the bizarre snapshot may perhaps be a decent representation of their relationship (via InStyle).

Even though the relationship was doomed, it appeared enjoyable while it was going on. According to InStyle, the two started dating in 2002 after being introduced by Gyllenhaal’s sister, Maggie. They later moved in together and even adopted a lovely dog named Atticus. However, the “it” pair of the early 2000s ultimately failed to make things work, probably because of commitment problems.

Just two months before their breakup, Dunst revealed to People, “Oh, I’m not old enough to wed. I’m 22 years old, really.” Unfortunately, they didn’t seem to stay particularly close after their 2004 breakup. It would be wonderful to see him, but we’re not close friends, Dunst said in 2009, as reported by Allure through Us Weekly.

2006: Natalie Portman

Natalie Portman, the star of “Black Swan,” and Jake Gyllenhaal were originally mentioned together in 2002, according to E! News, but they didn’t make news until 2006. Gyllenhaal, as usual, kept information about their romance discreet. According to reports, the two only dated briefly in 2006. They appeared in the 2009 movie “Brothers” together, thus it appears they were able to maintain their friendship even after their relationship ended (source: E! News).

When giving Portman a Desert Palm Achievement Award in 2011 for her work in “In “Black Swan,” Gyllenhaal said, “[I] was waiting in line for her to sign my Queen Amadala doll and I’m really hope she wins the Oscar. We first met at a Star Wars convention.

Because if she succeeds, the doll will be extremely valuable!” Despite their failed romance, Gyllenhaal seemed eager to express his admiration for the actress, referring to her as the “Audrey Hepburn of our generation” and praising her for being “graceful, has amazing eyebrows, and is talented, really short, funny, smart, dedicated, incredibly kind, and Jewish!”

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2007 – 2009: Reese Witherspoon

It is obvious from looking at Reese Witherspoon and Jake Gyllenhaal’s relationship that there were problems from the beginning. According to People, the two originally met in 2006 and become close friends while also having a small amount of a crush on one another.

The two grew close over the following few months, but by the summer of 2007, Witherspoon made the decision to separate. According to a source, “They parted ways. It’s finished, end of story. Reese had to carry out the task. She had recently gone through a divorce and was so preoccupied with her family that she simply didn’t have time for him, despite his adamant demands.”

However, later that year, the two began a formal relationship; Witherspoon called Gyllenhaal “a really lovely person.” She revealed to Vogue, per People, “He is very encouraging. I’ll just say that I’m really content with my life.” In terms of the relationship, Gyllenhaal was his typical reclusive self, a source close to the pair told People “She is a fantastic mother, which Jake finds attractive.

He desires a family and loves children dearly.” But Gyllenhaal’s portrayal of a “family man” seems to have contributed to their final breakup in 2009. Us Weekly reported that while Witherspoon was still recovering from her last divorce and wasn’t quite ready for wedding bells, Gyllenhaal was ready to settle down and get married.

2010: Taylor Swift

The relationship between Jake Gyllenhaal and Taylor Swift appears to be straight out of a Hallmark film in photos, with lots of hugs, smiles, and lattes on picturesque streets. However adorable they may have appeared to be together, the two split up in January 2011 despite being first seen together in October 2010. Gyllenhaal allegedly told Swift that things “simply weren’t working out,” and she was angry and left feeling “burned” by him, according to Us Weekly.

Swift processed her breakup by penning a song about her heartbreak, as many musicians do. Two years later, she released the song “All Too Well” from her album “Red,” which detailed their ups and downs in a relationship. Songs like “And you call me up again only to shatter me like a promise / So casually cruel in the name of being honest” were featured in the lyrics.

Gyllenhaal is a very private person, so it must be a little difficult for her to write a hit song (and probably several songs) about you. Swift, though, said that he handled the circumstance all too well: Taylor stated to New York Magazine (as reported by Us Weekly), “I recently listened to the record, and I have to say, it was incredibly sad for me. That was great. It was like looking through a photo book.”

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Rumored: Jessica Lowndes

All eyes were on Jake Gyllenhaal after his public and contentious breakup with Taylor Swift, including any dates he dared to go on. A few months after splitting from Swift, in April 2011, he was seen with Jessica Lowndes, an actress most known for her work in Hallmark films and TV shows including “90210” and “The Haunting of Molly Hartley.”

According to MTV, the two were apparently having breakfast together at the Greenwich Hotel in New York City. A witness reportedly told Glamour that the two were “quite friendly” as they visited a party together later that evening.

Going out on a few dates isn’t the same as committing to a relationship, and Gyllenhaal’s agent later confirmed to E! News that the actor and Lowndes were not dating. It’s difficult to determine for certain what was going on between Lowndes and Gyllenhaal because Lowndes’ agent merely responded “no comment” when asked if they were dating.

2018 – Present: Jeanne Cadieu

The French model Jeanne Cadieu, who was initially captured with Gyllenhaal while out for a stroll in Paris in 2018, completes our list. According to E!, they’ve mostly kept their relationship private; they don’t follow each other on Instagram and are barely ever seen together in public.

Gyllenhaal stated to British Vogue in May 2020 that for the foreseeable future, he wishes to focus more on his personal connections, ostensibly including his relationship with Cadieu. “I’ve turned to my family, my friends, and love because I realise that life is, you know, transitory and the world is the way it is right now,” he said. “I’d say I’m more interested in that and a little less interested in the work.”


  • Viraj Patil

    Viraj is a Content Editor currently working at Whistlernews.com, He intended to write on the most recent developments of Entertainment, Sports to News from his own unique angle. He is a Final Year Engineering student

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