Jake Gyllenhaal Dating History Over The Years – Hollywood Life

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Jake Gyllenhaal Jeanne Cadieu




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While the talented actor Jake Gyllenhaal‘s love life may be under the limelight lately due to Taylor Swift fans, he has been romantically linked to many other women over the years, most of them actresses and models. Read more about the Donnie Darko star’s dating history here.

Jenny Lewis and Jake GyllenhaalK-PAX10/22/01 Hollywood, CAJenny Lewis and Jake GyllenhaalPremiere of the new film "Donnie Darko" held at the Egyptian Theater in Hollywood
Jenny Lewis and Jake Gyllenhaal
Premiere of the new film “Donnie Darko” held at the Egyptian Theater in Hollywood. (Bei/Shutterstock)

Jake and Jenny Lewis, who was the lead singer of indie rock band Rilo Kiely, were together briefly in 2001, per Elite Daily. However, the two remained friends after their split, and Jake even took Jenny to the Golden Globes ten years later.

Kirsten Dunst Jake Gyllenhaal
Kirsten Dunst and Jake Gyllenhaal (Scott Myers/Shutterstock)

Reportedly set up by Jake’s sister Maggie Gyllenhaal, Jake and the Melancholia star were together from 2002-2004, per L’Officiel. Their relationship moved fast, as they moved in with each other and even adopted a dog together before their breakup. However, in 2009, Kirsten told Allure that the two no longer remained in contact regularly.

Natalie Portman Jake Gyllenhaal
Natalie Portman and Jake Gyllenhaal (Matt Baron/BEI/Shutterstock)

Jake and the Black Swan star reportedly had a several month fling in both 2002 and 2006. They stayed friends after their split, and even co-starred in the movie Brothers together in 2009.

Reese Witherspoon Jake Gyllenhaal
Reese Witherspoon Jake Gllyenhaal (Sandro Pace/AP/Shutterstock)

The two met while on the set of the film Rendition, and had a close knit romance from 2007 to 2009. This was shortly after Reese divorced her first husband Ryan Philippe. Jake reportedly became very close to Reese’s two children during their relationship, making their breakup in 2009 very emotionally difficult. While the cause of the split isn’t completely known, a source told E! that the spark between the two simply began to fade. Jake still spoke fondly of the Walk The Line actress years later, telling Entertainment Weekly in 2016 that Reese was “one of the smartest, strongest people I’ve ever met.”

Taylor Swift
Taylor Swift (SplashNews)

Perhaps one of the most controversial romance’s in Jake’s personal life, he and Taylor Swift had a three month stint in 2010, via US Weekly. Jake is around 10 years Taylor’s senior, and fans have heavily speculated that she wrote the song “All Too Well” about him off her 2012 album Red. In 2021, Taylor released a 10 minute revamped version of the song, accompanied with a short film. The film depicts the struggles of a couple with a large age gap with an emotionally distant male partner, via Glamour. When asked how he felt about the re-recorded song and the film, Jake told Esquire that he had no hard feelings towards Taylor, and denied that the video had anything to do with him, despite striking similarities between their relationship and the song’s lyrics and plot of the film.

Jake Gyllenhaal Alyssa Miller
Jake Gyllenhaal and Alyssa Miller (SplashNews)

Jake reportedly met the model at a gym in New York City, resulting in a romance that lasted six months. The two split in 2014, because Jake was too busy filming his movie Southpaw, per The Daily Mail.

Jake Gyllenhaal Jeanie Cadieu
Jake Gyllenhaal and Jeanie Cadieu (Matt Baron/Shutterstock)

As for his current romance, Jake has been involved with model Jeanne Cadieu since 2018. The pair keep their relationship mostly out of the limelight, however, they made their first red carpet appearance together in September of 2021. They quarantined together during the pandemic, and the actor even mentioned on The Howard Stern Show in October 2021 that he is open to marrying Jeanne in the future, via People.

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