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HomeRelationshipsJake Gyllenhaal Has an Impressive Dating History in Hollywood.

Jake Gyllenhaal Has an Impressive Dating History in Hollywood.

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At 40, Jake Gyllenhaal has never been married, but his dating history is quite impressive. The icon dated several Hollywood A-listers, before hooking up with current girlfriend, Jeanne Cadieu.

Jake Gyllenhaal’s girlfriend, Jeanne Cadieu has become a Hollywood sensation since she was first linked with the Sweden-born American actor. 

However, before going official with Cadieu, the 40-year-old explored the dating waters to the fullest. So far, he has landed himself some of the hottest chicks in the entertainment industry, including Taylor Swift and Kristen Dunst.

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Jake Gyllenhaal and Jeanne Cadieu | Image: Pinterest
Image: Pinterest


Jeanne Cadieu is a 24-year-old French model who seems to have captured the heart of one of Hollywood’s playboys. In the course of her modeling career, the star has done several campaigns and promotions, under the agency, IMG Models.

Going by her Instagram bio, Jeanne Cadieu is represented by Elite NYC and is a student at Columbia University. Although not as famous as her beau, the model has an impressive online presence, with over twenty-one thousand Instagram followers.

Interestingly, Gyllenhaal is not one of those followers as neither follows the other on Instagram nor shares pictures of them coupling up.


Despite being sixteen years older, Jake Gyllenhaal has embraced Jeanne Cadieu as his special woman. The duo first became linked in December 2018 following several public sightings.

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In July 2018, the couple went on a lowkey getaway in London, with pictures of their romantic moments captured by the press. A month later, they enjoyed another vacay in Greece, with the media capturing shots of them together.

While many wondered if the duo were together for real, Gyllenhaal gave the closest thing to a confirmation possible. During a Paris getaway, the “Nightcrawler” star shared a picture of the Eiffel Tower on social media, along with the caption:

“My own brokenness. My broken was attracted to your broken. Maybe that’s why I allowed you to break me.”

JakeGyllenhaal and Jeanne Cadieu | Image: Pinterest
Image: Pinterest

Although the post did not reveal the mystery target of the heartfelt message, it seemed fair enough to fit Cadieu as the missing puzzle piece. After all, she was the only love interest associated with him at the time.

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In September 2019, the two made a rare public outing in New York City, engaging in PDA as they strolled through the city. Again in June 2020, the two were relationship goals as they grabbed dinner in a Los Angeles restaurant while observing COVID-19 protocols.


Jake Gyllenhaal and Jeanne Cadieu | Image: Pinterest
Image: Pinterest

Having sustained their relationship for over two years, Jake Gyllenhaal and Jeanne Cadieu have easily become part of each other’s lives. The model has met the actor’s family and made acquaintance with several of his friends. Speaking on the “The Spider-Man: Far From Home” actor divulged:

“Jeanne is very mature for her age. She’s quirky, smart, and loves history. She and Jake really took things slow, but are now pretty serious.”

Their relationship has become more serious over the years. Reports also show that the duo embarked on a joint art project, The “Inside Out” in 2019, featuring several portraits of them and many others, which hung outside the Hudson Theatre.


The showbiz legend has been open about his plans of having a family with kids in the picture. During an interview in May 2020, the entertainment icon discussed how much he wanted kids. Going further, he noted that his character on “Sunday In The Park With George” mirrored his ideal fatherhood goals.

Jake Gyllenhaal also pointed out how much he’d lightened up since resolving to focus on his relationships, most notably, with Jeanne Cadieu. In a previous interview, the actor also discussed his fatherhood dreams, admitting he hoped to become a father someday.


While Jake Gyllenhaal attributes his refusal to go down the marriage path to fear, he never shies away from dating. Notably, he has also admitted to falling in love just twice in his lifetime. However, he failed to name the lucky recipients of his untainted affection.

And with a long list of beautiful and talented women on his dating portfolio, fishing out two names seems unlikely.

Jake Gyllenhaal and Taylor Swift | Image: Pinterest
Image: Pinterest

In 2001, Gyllenhaal dated songstress, Jenny Lewis, with the duo coupling up at the 2001 Golden Globes. After their romance ended, he hooked up with “Spider-Man” star, Kirsten Dunst thanks to his sister’s matchmaking antics. Their relationship lasted until 2004.

Two years after split from Dunst, the Hollywood legend had a brief affair with actress Natalie Portman. In 2007, Gyllenhaal’s romance with actress Reese Witherspoon commenced. Sadly, they broke up in December 2009.

October 2010 marked the onset of his brief fling with singer, Taylor Swift. They embarked on several trips together, had family visits, and enjoyed their infamous Maple Latte outing which went viral.


Jake Gyllenhaal and Alyssa Miller | Image: Pinterest
Image: Pinterest

Between 2011 and 2013, Gyllenhal was linked with several stars, including Anna Kendrick, Jessica Lowndes, Minka Kelly, and Emily DiDonato. However, none of these flings lasted long enough to receive an official confirmation.

From 2013 to 2014, he dated Alyssa Miller. Following their separation, the icon moved on to his “Constellation” co-star Ruth Wilson. Although they never confirmed the romance, the twosome was caught kissing in public on occasions.

Eventually, the French model Jeanne Cadieu came into Jake Gyllenhaal’s life and so far represents one of the actor’s longest-lasting romance with an A-lister.

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