Gyllenhaal and Swift sparked dating rumours after attending "Saturday Night Live" together in October 2010 after reportedly meeting through actress Gwyneth Paltrow at a dinner that year. In November 2010, the two were spotted walking together in Brooklyn while smiling and embracing. They even spent the Thanksgiving holiday with Gyllenhaal's sister, Maggie Gyllenhaal.
The couple's relationship was short-lived, however. By December 2010, the two went their separate ways. Regarding their breakup, a source told Us Weekly, "Jake just told her it wasn't working out. Taylor is really upset and hurt. She feels really burned by him."
Two years later, Swift alluded to their relationship in her 2012 song "All Too Well." At one point in the song, Swift sings, "I left my scarf there at your sister's house / And you've still got it in your drawer even now." She continues, "But you keep my old scarf from that very first week / 'Cause it reminds you of innocence / And it smells like me." The infamous scarf Swift is referring to is believed to be the one she was pictured in while strolling with Gyllenhaal back in November 2010 while they spent Thanksgiving with Maggie.
Swift rereleased "All Too Well" in 2021 as part of her rerecorded album "Red (Taylor's Version)" and further detailed their three-month-long relationship. In the 10-minute version of the song, she sings, "They say all's well that ends well / But I'm in a new hell every time you double-cross my mind / You said if we had been closer in age maybe it would have been fine / And that made me want to die."