Investigating the Dating History of Jake Gyllenhaal

It’s hard to exist in Hollywood without having everyone clocking your personal life at all times and it’s especially difficult when you’ve been famous for decades and have publically dated several other fellow celebrities.

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That is certainly the case with actor Jake Gyllenhaal.

He previously told British Vogue “Yes, I do. Of course I do” when asked if he saw children in his future and said he’s recently “turned to my family, I’ve turned to my friends and I’ve turned to love.”

Who is Gyllenhall’s current love and how did he get there?

From ‘Donnie Darko’ To Broadway: Jake Gyllenhaal’s Varied and Impressive Career

Jacob Benjamin Gyllenhaal was born in Los Angeles, California on December 19, 1980, per Biography. His parents are director Stephen Gyllenhaal and producer and screenwriter Naomi Foner and his sister is actress Maggie Gyllenhaal. He appeared as a child in movies such as City Slickers and A Dangerous Woman and broke through with the 2001 indie classic Donnie Darko along with costar sister Maggie. He followed it up with memorable performances as a depressed teen who calls himself Holden after Catcher In The Rye’s Holden Caufield in The Good Girl opposite Jennifer Aniston and a man mourning the death of his fiancee in Moonlight Mile.

In 2005, Gyllenhaal costarred alongside Heath Ledger in Ang Lee’s Brokeback Mountain, in which he played Jack Twist, a rodeo rider who has a secret, decades-long affair with fellow cowboy Ennis Del Mar. He was nominated for an Oscar and won a BAFTA for his performance. He continued taking diverse, interesting roles in films, including playing a boxer in Southpaw, a cameraman who specializes in recording grisly crime scenes in Nightcrawler, and the hyperactive Mr. Music on John Mulaney’s Netflix series parodying children’s television, John Mulaney & The Sack Lunch Bunch.

In addition to his work in television and movies, Gyllenhaal has also appeared in theater productions on Broadway and in London’s West End. In 2002 he starred in a revival of This Is Our Youth. He made his Broadway debut in Constellations in 2015 and returned in 2017 to play artist Georges Seurat in a revival of the Sondheim musical Sunday In The Park with George. From 2019 to 2020, he did a run of Simon Stephens’ Sea Wall/A Life, for which he has been nominated for his first Best Actor Tony.

Gyllenhaal’s Long List of Famous Girlfriends

Jake Gyllenhaal’s first high-profile romance was with actress Kirsten Dunst. Introduced by Jake’s sister Maggie Gyllenhaal, the couple dated from 2002 to 2004, as reported by Us Weekly. A famous paparazzi shot of the two sitting at a table as Gyllenhaal watches Dunst eat a salad with her fingers still periodically makes the rounds on social media.

Gyllenhaal’s romantic life stayed in the spotlight as he dated fellow celebs actress Natalie Portman in 2006 and actress Reese Witherspoon from 2007 to 2008. His brief 2010 relationship with singer-songwriter Taylor Swift was immortalized in her song “All Too Well.” Gyllenhaal reportedly broke up with Swift a few months into their relationship. In 2020, he posted a childhood picture of himself wearing glasses on Instagram to honor the organization New Eyes for the Needy. Swifties reportedly “flooded the comments section” of the post with the “All Too Well” lyric “You used to be a little kid with glasses in a twin-sized bed.”

Alyssa Miller

Per Marie Claire, Gyllenhaal dated model Alyssa Miller from 2013 to 2014. He was first rumored to be dating French model Jeanne Cadieu in 2018; E! Online posted a picture of them arm in arm enjoying “a cozy stroll” in Paris. The two appeared together on the red carpet for the premiere of Spider-Man: Far From Home as well as at a party for jewelry brand Cartier.

A 2019 Page Six article noted that the pair were “getting serious” and that girlfriend Jeanne Cadieu had accompanied Jake’s entire family on a vacation to Martha’s Vineyard. This does seem to be Gyllenhaal’s longest relationship yet; time will tell if he’s ready to settle down now that he’s nearly 40 and, as he told British Vogue, “turned toward love.”

Gyllenhaal and Jeanne Cadieu

Gyllenhaal and Jeanne Cadieu were first linked in late 2018, and only now are becoming more open with their relationship.

The two kept their relationship quiet for almost three years before making a red carpet appearance in late-2021at the premiere of The Lost Daughter — which was to support Maggie Gyllenhaal’s directorial debut.

Cadieu is 15 years his younger being just 26 years old to Gyllenhall already 41, set to turn 42 in December.

Despite the age difference the two share common interests, including a similar degree path at Columbia which she finished and he dropped out at Columbia University.

While he was on The Howard Stern Show in October 2021, Gyllenhaal added one of the reason that they get along is that she does not get wrapped up in “​​all the other stuff.”

“That’s part of the reason why I just adore her,” he said. “And not at all the main reason but, you know, one of them.”

What do you think?

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