The twosome were originally seen spending time together in October 2010 and dated for three months before going their separate ways. Two years later, Swift made headlines with her album Red, which included smash hits “All Too Well” and “We Are Never Ever Getting Back Together.”
Swifties were quick to to dig for clues within the lyrics, which not-so-subtly hinted at Swift and Gyllenhaal’s whirlwind relationship. While Swift didn’t specify which of her famous exes the tracks were about, she revealed that the subject of her songs instantly connected the dots.
“He was like, ‘I just listened to the album, and that was a really bittersweet experience for me. It was like going through a photo album.’ That was nice,” the Grammy winner recalled during an interview with New York magazine in November 2013 . “Nicer than, like, the ranting, crazy e-mails I got from this one dude.”
While fighting to win back ownership of her masters from her former record label, Big Machine, Swift decided to rerecord all of her past albums. As she looked back on her old songs, the Pennsylvania native offered a glimpse at what inspired her to write “All Too Well” in the first place.
“It was a day when I was just, like, a broken human, walking into rehearsal just feeling terrible about what was going on in my personal life,” she explained during an episode of Rolling Stone’s “500 Greatest Albums” podcast in 2020. “I ended up sort of just playing four chords over and over again, and the band started kicking in. … People just started playing along with me. I think they could tell I was really going through it. I just started singing and riffing and sort of ad-libbing this song that basically was ‘All Too Well.'”
The following year, Swift announced the return of the Red era with 30 tracks on her version of the now-iconic album, including a 10-minute rendition of “All Too Well.” The new-and-improved Red follows her rerelease of 2010’s Fearless, which featured a never-before-heard song titled “Mr. Perfectly Fine.”
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The lyrics for the April 2021 track read, “Hello, Mr. ‘Perfectly fine’ / How’s your heart after breaking mine? / Mr. ‘Always at the right place at the right time,’ baby / Hello Mr. ‘Casually cruel’ / Mr. ‘Everything revolves around you’ / I’ve been Miss ‘Misery’ since your goodbye and you’re Mr. ‘Perfectly fine.’”
While it’s unclear who she is describing, some listeners noticed Swift’s use of “casually cruel” in both “Mr. Perfectly Fine” and “All Too Well,” speculating that the Guilty actor was the man in question.
Scroll down to relive Swift’s relationship with Gyllenhaal — and to see how it impacted the writing on Red: