![]() ![]() ![]() Still, in 2016, Gyllenhaal spoke glowingly of his ex, telling Entertainment Weekly that Witherspoon 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. But at the time, a source told E! that their spark simply “fizzled.” When they split in late 2009, fans were heartbroken. He reportedly spent a lot of time with Witherspoon’s kids, Ava and Deacon, and even accompanied the family up to Ojai on weekends where they’d stay on Witherspoon’s farm, be merry, and grow vegetables. 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. In October 2008, she told Vogue, "He's very supportive. After her divorce from Ryan Philippe, Witherspoon started dating Gyllenhaal in early 2007, and often spoke about their relationship to the press. Gyllenspoon’s love was really something special. She even nodded to the now-infamous scarf in her We Are Never Ever Getting Back. 2001: Jenny Lewisįrazer Harrison/Getty Images Entertainment/Getty Images Swift was seen donning a striped scarf while out with actor Jake Gyllenhaal, the song’s rumored subject. Read on for everything you need to know about Jake Gyllenhaal’s dating history. So sit back and allow Gyllenhaal’s dating history to take you on a journey - back to the early aughts, back to the Donnie Darko days, back to when he was little more than a scraggly mustache in an oversized blazer on the arm of then-girlfriend Jenny Lewis. Whether you’re a Swiftie doing your due diligence on Taylor’s exes or a Brokeback Mountain stan, it’s fun to take a trip down memory lane and remember all the names in Gyllenhaal’s little black book. Gyllenhaal, who’s nine years older than Swift, and whose current girlfriend is 15 years his junior, has faced a lash of scrutiny from Swifties who are, shall I say, skeptical of his dating habits. Taylor Swift’s 10-minute version of All Too Well, released with much fanfare earlier this month as part of the rerecorded reissue of her. While it’s not been outright confirmed by Swift herself, certain tracks on the album, especially breakup anthem “All Too Well,” are thought to be nods to her brief, three-month relationship with the actor. Gyllenhaal’s dating history has gone under the microscope lately in the wake of Taylor Swift’s 2021 re-release of her 2012 album Red. Over the years, the 41-year-old actor has had several notable romances - from fellow actors Kirsten Dunst and Reese Witherspoon to pop icon Taylor Swift - some of whom have been co-stars, musicians, or models. Long before there was Red (Taylor’s Version), Jake Gyllenhaal was busy breaking Gyllen-hearts left and right. ![]()
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