Swift and Gyllenhaal's romantic history dates back to when they were set up by actress and mutual friend Gwyneth Paltrow. In December 2010, Paltrow reluctantly told USA Today that she played matchmaker after a report surfaced indicating that Swift, just 20 years old at the time, and a 29-year-old Gyllenhaal, met at a dinner party at the London home Paltrow shared with then-husband Chris Martin.

"I've just known Jake for a long time, and he's a great guy," she said, "and Chris has a friendship with Taylor."

She added, "It's so weird. I wonder how people find out these things. It was a while ago, so I don't know why it would come out today."

Admitting she was "scared to say," the only timeline Paltrow gave for the dinner party was "a while ago." However, it was clear by October of that year that something was brewing between Swift and Gyllenhaal.

The cultural icon and her beau were first seen together backstage at a taping of Saturday Night Live in October 2010. A source told People they had shown up to the SNL taping together, and that "they walked around together backstage, but they were careful not to be seen too close. It was hard to tell if they were together, but everyone was shocked that she brought him."

The folklore singer-songwriter and Prisoners actor were first seen together backstage at a taping of Saturday Night Live in October 2010. A source told People they had shown up to the SNL taping together and that "they walked around together backstage, but they were careful not to be seen too close. It was hard to tell if they were together, but everyone was shocked that she brought him."

By 2011, the autumnal coffee dates and strolls were officially done after the pair reportedly spent the holiday apart. The Grammy Award-winning musician rang in the new year solo in Nashville, while the Ambulance star was in New York City, where he attended a closing party for Broadway's Fela! on January 2. A source confirmed the breakup to People in early January with an aptly succinct quote, telling the outlet, "They're over. It ended last month."

Though the source didn't give a reason for the split, the relationship (and, presumably, the breakup) appeared to provide fodder for one of Swift's most popular hits. It's now widely accepted that "All Too Well" from Swift's 2012 Red album was penned about her relationship with Gyllenhaal, with all of its references to the subject having once been "a little kid with glasses" and a scarf left at his sister's house (hi, Maggie Gyllenhaal).

The rumor that the song is about the actor was so widespread that Maggie was forced to publicly answer for the scarf's whereabouts in an interview on Watch What Happens Live with Andy Cohen in 2017. 

"I am in the dark about this scarf. It's totally possible [it's at my house]," she told the WWHL host. "I don't know. I have been asked this before, and I am like, 'What are you talking about?'"