Jake Gyllenhaal’s dating history

Jake Gyllenhaal is a popular American actor who has been in the entertainment industry for more than 30 years. He started his acting career as a child actor and made his debut with the comedy film City Slickers in 1991. He is best known for his work in Brokeback Mountain (2005), Love & Other Drugs (2010), Everest (2015), Spider-Man: Far From Home (2019), Spider-Man: No Way Home (2021), etc.

Gyllenhaal has been nominated many times for major awards including an Academy Award, 3 BAFTA Awards, 3 Golden Globe Awards, 3 SAG Awards, and more. Over the years, along with his acting projects, his dating life has been in the spotlight many times. Let’s take a look at Jake Gyllenhaal’s dating life over the years.

Kirsten Dunst

Jake Gyllenhaal started dating Kirsten Dunst in September 2002. They were introduced to each other by Gyllenhaal’s sister, Maggie Gyllenhaal, who was Dunst’s co-star in the 2003 film Mona Lisa Smile. They had a serious relationship as they moved in together to a $1.7 million house in Los Angeles and adopted a German Shepherd, according to People. They ended their relationship in July 2004 but remained friends, and the reason for their breakup was not revealed.

Reese Witherspoon

Jake Gyllenhaal started dating Reese Witherspoon in 2007. They met on the sets of the 2007 film Rendition. They also went on vacations to Paris and Marrakech in 2008. In an interview with Vogue in 2008, Reese gave insights into her relationship with Gyllenhaal and shared, “He’s very supportive. Suffice it to say, I’m very happy in life, and I’m very lucky to have a lot of really supportive people around me who care very much for me, and, you know, that’s all you can hope for in life. I am very blessed in that way.”

After dating for almost 3 years, they ended their relationship in December 2009. In 2016, in The Jess Cagle Interview episode, Gyllenhaal shared that there are no hard feelings between them and said, “She is, as I would say about most of the women who I’m close friends with or had relationships in my life, one of the smartest, strongest people I’ve ever met.”

Taylor Swift

Jake Gyllenhaal started dating Taylor Swift in late 2010. The news of their dating came out when they were spotted by the paparazzi together in New York and later when they were spending Thanksgiving together. Their relationship was short-lived, as they ended it by the end of the year. Their relationship has been talked about a lot amongst Taylor Swift’s fans and the media. There is speculation that many songs on her album Red, which was released in 2012, were inspired by him, especially 'All Too Well.'

In 2022, Swift released a 10-minute version of the song 'All Too Well,' which made people speculate even more that the song was inspired by Gyllenhaal. In an interview with Esquire in 2022, Gyllenhaal addressed the speculation and said, “It has nothing to do with me. It's about her relationship with her fans. It is her expression. Artists tap into personal experiences for inspiration, and I don't begrudge anyone that."

Alyssa Miller

Jake Gyllenhaal and model Alyssa Miller started dating in June 2013. They were spotted together by the paparazzi in New York. They met each other for the first time in a gym in New York. In an interview with US, Miller shared details about her relationship with Gyllenhaal and said, “Things are good, I have people over all the time and we cook, he's the teacher." According to People, their relationship ended in 2014.

Jeanne Cadieu

Jake Gyllenhaal and French model Jeanne Cadieu started dating in 2018. They were spotted together spending time in New York and Paris. They kept their relationship private until 2021 when they made their red carpet debut as a couple at the screening of the film The Lost Daughter, directed by his sister Maggie Gyllenhaal. Since then, they have walked many red carpets together.

In an interview with Esquire in 2022, Gyllenhaal shared that the pandemic brought them even closer together. He said, “In a lot of ways, we're family. I'm in a relationship that is full of love and support. I feel so at ease." The couple has been dating for six years now.

Also read about: Jake Gyllenhaal's Net Worth