Jake Gyllenhaal’s Dating History: From Kirsten Dunst to Taylor Swift

Hey, heartbreaker! Jake Gyllenhaal has had his fair share of high-profile relationships — and headline-worthy breakups — through the years. Early in his career, the California native struck a romance with Kirsten Dunst — and nearly starred opposite her in 2004's Spider-Man 2 amid concerns over Tobey Maguire's health. The pair dated for two years after being introduced by Jake's sister, Maggie Gyllenhaal, and even shared a home in the Hollywood Hills. Ultimately, the duo couldn't make it work and called it quits in 2004. Following his split from the On Becoming a God in Central Florida actress, the Oscar nominee was linked to major movie stars including Natalie Portman and Reese Witherspoon. One of his most unforgettable relationships, however, was his brief fling with Taylor Swift. The Nocturnal Animals actor and the "Gorgeous" singer began dating in late 2010 but their honeymoon phase didn't last long. When they split just before the start of the new year, a source told Us Weekly, "Jake just told her it wasn't working out." At the time, Swift was "really upset and hurt" and felt "really burned" by her ex. Two years after they called it quits, Swift released a scathing breakup anthem titled "All Too Well," which fans were quick to decode as a diss toward the Tony Award nominee. While the Pennsylvania native's love life didn't lose momentum after her 2010 split, her diehard fans have never forgiven Jake. In August 2020, the actor faced the wrath of Swifties on Instagram after sharing a throwback pic of himself wearing a pair of glasses. "U posted this pic and thought that the swifties would do nothing???? mistake," one fan teased in the comments. Others referred to lyrics from "All Too Well," writing, "You used to be a little kid with glasses in a twin-sized bed." The Miss Americana star went on to release Red (Taylor's Version) in November 2021, putting her brief romance with Gyllenhaal front and center again. Swift gifted her fans with a 10-minute version of "All Too Well" on the 30-track record, also creating a short film for the track starring Sadie Sink and Dylan O'Brien. Though he's faced a few ups and downs over the years, the Spider-Man: Far From Home actor found something solid with girlfriend Jeanne Cadieu. Us broke the news in December 2018 that the twosome, who boast a nearly 15-year age difference, began dating six months earlier and were getting "pretty serious." The City Slickers star has kept his romance with the France native under wraps, but in May 2020, he hinted that he was ready to settle down. "I definitely do [want kids]," he told British Vogue at the time. "I'm not someone who has ever existed in a space where I've really known what's coming next. But you do have to be open to it. ... [I'm] seeing life as something that is, you know, fleeting, and the world being as it is now, I've turned to my family, I've turned to my friends and I've turned to love." Scroll down for a closer look at Jake's love life: