When Red (Taylor’s Version) re-hit the airwaves, we were all reminded of a short-lived romance with a long-term effect: Taylor Swift and Jake Gyllenhaal. With the release of a 10-minute “All Too Well" video, the drama and the scarf were repositioned to the front of celebrity discourse with major names hopping on the T-Swift wagon including the legend Dionne Warwick who tweeted, “If that young man has Taylor’s scarf he should return it. It does not belong to you. Box it up and I will pay the cost of postage, Jake.”
Despite the heat, Gyllenhaal finds himself in a new and distinct chapter: domesticated. In December 2018, Us broke the story that Gyllenhaal was serious with his girlfriend Jeanne Cadieu, a model nearly 15 years his junior.
The Nightcrawler actor has kept his long-term relationship with the French model quite private, but in October 2021, he spoke to Howard Stern about wanting to expand his role as husband and father.
"That's all I want is to be a good husband and a father," Gyllenhaal told Stern. "That really is what I want and now that I have fulfilled a lot of things in my career that I feel comfortable with, I can safely say that. I don't know if I could have said that before."
But for those who are concerned this may slow down his acting career, he pointed to his sister Maggie Gyllenhaal as inspiration. "Her life, her family, and her marriage has just deepened her work," he said, "I think there comes a point where you either start getting more shallow or you start getting more deep in your work, and I think you have to incorporate those things into your life in order for that to happen."
L'OFFICIEL does a deep dive into the celebrity's actress-filled dating history.
Jenny Lewis
The actor dated the Rilo Kiley frontwoman in the early 2000s; despite their romance fizzling out, the duo remains friends.
Kirsten Dunst
After a set-up by sister Maggie, teen-icon Kirsten Dunst and Gyllenhaal entered a two-year-long relationship from 2002-2004. They even ended up living together and adopting a German Shepherd, though they called it quits in December 2004.
Natalie Portman
Gyllenhaal briefly dated actress Natalie Portman in 2006. The actors went on to co-star in the 2009 movie Brothers, and remain good friends.
Reese Witherspoon
Witherspoon met Gyllenhaal while filming Rendition, where a slow burn of a crush turned into a relationship from 2007-2009. According to sources, the pair left one another on good terms.
Taylor Swift
In late 2010, the three-month tryst heard round the world, Swift and Gyllenhaal met, fell for another, and dissipated. Swift went on to write "All Too Well" and "We Are Never Ever Getting Back Together" about the star. We are waiting on the scarf to be returned.
Jessica Lowndes
At NYC's Greenwich Hotel in April 2011, it is rumored Gyllenhaal had a momentary blip with the 90210 actress.
Alyssa Miller
With two years of single life under his belt, Gyllenhaal began dating Sports Illustrated Swimsuit model Alyssa Miller after meeting at the gym in June 2013. Miller was later spotted at the Angel Ball and gushed about the romance saying Gyllenhaal was “the teacher.”
Jeanne Cadieu
The 25-year-old model and Gyllenhaal have been an item since 2018. Their relationship has been largely under wraps as both maintain a notable absence of one another on their respective social media.
