When: October 2010 — January 2011
Gyllenhaal and Swift began quietly dating and sharing maple lattes together in the fall of 2010, and per Marie Claire, it was rumored Gyllenhaal was so enchanted by her that he dropped $160,000 just so he could fly her in on a private jet for a date. Talk about getting bit by the love bug, huh?
By New Year's Eve, however, Gyllenhaal and Swift had gone their separate ways. Swift got all of her emotions about their relationship out in "All Too Well," with lyrics like, "Oh, your sweet disposition and my wide-eyed gaze / We're singing in the car, getting lost upstate / The autumn leaves falling down like pieces into place, and I can picture it after all these days."
In 2021, Swift released a 10-minute version of "All Too Well" along with a short film starring Sadie Sink that provided even more details about their relationship's emotional conclusion.
Neither Swift or Gyllenhaal have ever directly confirmed the song is about their romance, but after the long version's release, Swift's fans flocked to his social media to criticize him, so much that he had to turn off comments on his Instagram. "It has nothing to do with me. It's about her relationship with her fans," he told Esquire in February. "It is her expression. Artists tap into personal experiences for inspiration, and I don't begrudge anyone that."
