{"id":215346,"date":"2024-03-20T18:28:23","date_gmt":"2024-03-20T18:28:23","guid":{"rendered":"https:\/\/michigandigitalnews.com\/index.php\/2024\/03\/20\/his-dating-history-hollywood-life\/"},"modified":"2025-06-25T17:20:17","modified_gmt":"2025-06-25T17:20:17","slug":"his-dating-history-hollywood-life","status":"publish","type":"post","link":"https:\/\/michigandigitalnews.com\/index.php\/2024\/03\/20\/his-dating-history-hollywood-life\/","title":{"rendered":"His Dating History \u2013 Hollywood Life"},"content":{"rendered":"

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Image Credit: John Nacion\/Variety via Getty Images<\/figcaption><\/figure>\n

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While the talented actor<\/a> Jake Gyllenhaal<\/strong><\/a>\u2018s love life may be under the limelight due to Taylor Swift<\/strong><\/a> 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<\/em> star\u2019s dating history here. Most recently, he brought his girlfriend, Jeanne Cadieu<\/strong>, to the New York premiere of his 2024 action movie, Road House<\/em><\/a>.<\/p>\n

\"Jenny
Jenny Lewis and Jake Gyllenhaal
Premiere of the new film \u201cDonnie Darko\u201d held at the Egyptian Theater in Hollywood. (Bei\/Shutterstock)<\/figcaption><\/figure>\n

Jake and Jenny Lewis<\/strong>, who was the lead singer of indie rock band Rilo Kiely, were together briefly in 2001, per\u00a0Elite Daily<\/em><\/a>. However, the two remained friends after their split, and Jake even took Jenny to the Golden Globes ten years later.<\/p>\n

\"Kirsten
Kirsten Dunst and Jake Gyllenhaal (Scott Myers\/Shutterstock)<\/figcaption><\/figure>\n

Reportedly set up by Jake\u2019s sister Maggie Gyllenhaal<\/strong><\/a>, Jake and the Melancholia<\/em> star were together from 2002-2004, per L\u2019Officiel<\/a><\/em>. Their relationship moved fast, as they moved in with each other and even adopted a dog together before their breakup. However, in 2009, Kirsten\u00a0<\/strong><\/a>told\u00a0Allure\u00a0<\/em>that the two no longer remained in contact regularly.<\/p>\n

\"Natalie
Natalie Portman and Jake Gyllenhaal (Matt Baron\/BEI\/Shutterstock)<\/figcaption><\/figure>\n

Jake and the\u00a0Black Swan\u00a0<\/em>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\u00a0Brothers<\/em> together in 2009.<\/p>\n

\"Reese
Reese Witherspoon Jake Gllyenhaal (Sandro Pace\/AP\/Shutterstock)<\/figcaption><\/figure>\n

The two met while on the set of the film\u00a0Rendition<\/em>, and had a close knit romance from 2007 to 2009. This was shortly after Reese<\/strong><\/a> divorced her first husband Ryan Philippe<\/strong>. Jake reportedly became very close to Reese\u2019s two children during their relationship, making their breakup in 2009 very emotionally difficult. While the cause of the split isn\u2019t completely known, a source told\u00a0E!<\/em> that the spark between the two simply began to fade. Jake still spoke fondly of the\u00a0Walk The Line\u00a0<\/em>actress years later, telling\u00a0Entertainment Weekly<\/em> in 2016 that Reese was \u201cone of the smartest, strongest people I\u2019ve ever met.\u201d<\/p>\n

\"Taylor
Taylor Swift (SplashNews)<\/figcaption><\/figure>\n

Perhaps one of the most controversial romance\u2019s in Jake\u2019s personal life, he and\u00a0Taylor Swift\u00a0<\/strong><\/a>had a three month stint in 2010, via US Weekly<\/em><\/a>. Jake is around 10 years Taylor\u2019s senior, and fans have heavily speculated that she wrote the song \u201cAll Too Well\u201d about him off her 2012 album Red.<\/em> 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\u00a0Glamour<\/em><\/a>. When asked how he felt<\/a> about the re-recorded song and the film, Jake told\u00a0Esquire<\/em><\/a> that he had no hard feelings towards Taylor, and denied that the video had anything to do with him, despite striking similarities<\/a> between their relationship and the song\u2019s lyrics<\/a> and plot of the film.<\/p>\n

\"Jake
Jake Gyllenhaal and Alyssa Miller (SplashNews)<\/figcaption><\/figure>\n

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\u00a0Southpaw<\/em>, per\u00a0The Daily Mail<\/em><\/a>.<\/p>\n

\"Jake
Jake Gyllenhaal and Jeanie Cadieu (Matt Baron\/Shutterstock)<\/figcaption><\/figure>\n

As for his current romance, Jake has been involved with model Jeanne Cadieu<\/strong> since 2018. The pair keep their relationship mostly out of the limelight, however, they made their first red carpet<\/a> appearance together in September of 2021. They quarantined together during the pandemic, and the actor even mentioned on\u00a0The Howard Stern Show <\/em>in October 2021 that he is open to marrying Jeanne in the future, via\u00a0PEOPLE<\/em><\/a>.<\/p>\n

At the March 2024 premiere of Road House<\/em><\/a>, Jake brought Jeanne along for a rare red carpet appearance together.<\/p>\n<\/p><\/div>\n

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[ad_1] View gallery Image Credit: John Nacion\/Variety via Getty Images While the talented actor Jake Gyllenhaal\u2018s love life may be under the limelight due to<\/p>\n","protected":false},"author":1,"featured_media":215347,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"_monsterinsights_skip_tracking":false,"_monsterinsights_sitenote_active":false,"_monsterinsights_sitenote_note":"","_monsterinsights_sitenote_category":0,"_uf_show_specific_survey":0,"_uf_disable_surveys":false,"footnotes":""},"categories":[156],"tags":[],"_links":{"self":[{"href":"https:\/\/michigandigitalnews.com\/index.php\/wp-json\/wp\/v2\/posts\/215346"}],"collection":[{"href":"https:\/\/michigandigitalnews.com\/index.php\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/michigandigitalnews.com\/index.php\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/michigandigitalnews.com\/index.php\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/michigandigitalnews.com\/index.php\/wp-json\/wp\/v2\/comments?post=215346"}],"version-history":[{"count":3,"href":"https:\/\/michigandigitalnews.com\/index.php\/wp-json\/wp\/v2\/posts\/215346\/revisions"}],"predecessor-version":[{"id":335677,"href":"https:\/\/michigandigitalnews.com\/index.php\/wp-json\/wp\/v2\/posts\/215346\/revisions\/335677"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/michigandigitalnews.com\/index.php\/wp-json\/wp\/v2\/media\/215347"}],"wp:attachment":[{"href":"https:\/\/michigandigitalnews.com\/index.php\/wp-json\/wp\/v2\/media?parent=215346"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/michigandigitalnews.com\/index.php\/wp-json\/wp\/v2\/categories?post=215346"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/michigandigitalnews.com\/index.php\/wp-json\/wp\/v2\/tags?post=215346"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}