Jake Gyllenhaal’s Dating Status Should Definitely Be "It’s Complicated"

Jake Gyllenhaal’s Dating Status Should Definitely Be "It’s Complicated"


Jake Gyllenhaal may be just entering into the Marvel universe with his role as Mysterio in the upcoming Spider-Man: Far From Home, but fans have long speculated about who Gyllenhaal is dating during his time in Hollywood.

The actor comes from a film-making family, including sister Maggie Gyllenhaal, so there has naturally been speculation about which lucky lady is occupying the actor’s heart. (Even though he’ll always admittedly fill space in ours.) Rumored romances have popped up often, but the Oscar-nominated actor has been involved in a few confirmed, high-profile relationships. But lately, Gyllenhaal has been keeping his private life, well, private.

Just because the Brokeback Mountain actor isn’t offering up statements about who he’s dating, doesn’t mean we won’t see him get his happily ever after at some point. In a 2015 interview with Howard Stern, the actor expressed his desire to get married: "Oh, I hope so. I think it’s hard for everybody, but I also think at some point, you just decide to grow up, you know? If you find the right person . . . I believe in monogamy. I believe when you meet somebody right, it will be right, and it will stay that way."

In the same interview, the actor also divulged that he’d been truly in love twice. Which of his famous exes, rumored or confirmed, were one of the two? Let’s take a look back to find out…

Kirsten Dunst

Gyllenhaal’s first high-profile relationship was with Kirsten Dunst from 2002 to 2004. Gyllenhaal’s sister reportedly set the couple up, which also led to an iconic set of photos in the summer of 2003 when the pair ate salad in London. (Seriously, take a long look.) When this young couple broke up, Gyllenhaal’s rep confirmed the news, per E!. "Kirsten and Jake remain the best of friends," his rep said at the time. Dunst welcomed a son with Jesse Plemons in 2018.

Reese Witherspoon

By 2007, Gyllenhaal had begun dating his Rendition co-star, Reese Witherspoon. The relationship began shortly after her divorce from Ryan Phillippe. Gyllenhaal and Witherspoon were frequently photographed alongside the actress’s two kids. By 2009, the pair had split. But there’s no bad blood here. In a 2016 Entertainment Weekly interview, Gyllenhaal referred to his former partner as, "One of the strongest, smartest people I’ve ever met."

Taylor Swift

Speaking of "Bad Blood"… once upon a time, Gyllenhaal and Taylor Swift had quite the love affair. In fall 2010, photos of the couple strolling around New York in chunky scarves, holding lattes emerged. By early 2011, this obsessed-over couple had blown away like the fall leaves. But remnants of the relationship found their way into tracks on Swift’s 2012 album Red, including "All Too Well," which references Swift leaving a scarf at Maggie Gyllenhaal’s house. (Why isn’t this preserved in the Smithsonian?!)

Alyssa Miller

In summer 2013, Gyllenhaal was linked to Sports Illustrated model Alyssa Miller. In 2014, the couple reportedly broke up because of distance during Gyllenhaal’s busy filming schedule.

Ruth Wilson

While working on the Broadway play Constellations in 2015, rumors swirled of a showmance between co-stars Ruth Wilson and Gyllenhaal. But, other than a few photos of the cast mates on cozy outings, there was never official word on the state of their relationship.

Jeanne Cadieu

That brings us to Gyllenhaal’s current relationship status. And, sorry to disappoint those with vision boards of a marriage to Gyllenhaal, it looks like the actor is taken. Per Us Weekly, Gyllenhaal has been dating 22-year-old model Jeanne Cadieu since some time in 2018. They’ve reportedly traveled to London and Greece together, but are keeping their love totally under wraps, not even following the other on Instagram.

So…Gyllenhaal’s maybe, sort of, taken. Although, knowing the elusive actor, a confirmation would be the exception to his relationship rule.

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