Inside Taylor Swift and Jake Gyllenhaal’s Short-Lived Romance

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Inside Taylor Swift and Jake Gyllenhaal’s Short-Lived Romance

A lasting impression. Taylor Swift and Jake Gyllenhaal’s relationship may have been brief, but its impact certainly hasn't been. 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.'" [jwplayer JR9BQ88D-zhNYySv2] 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." 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:

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The Whirlwind Romance

The duo initially sparked romance rumors after they attended Saturday Night Live together in October 2010 to support host Emma Stone. Shortly after their night out together, Swift appeared on The Ellen DeGeneres Show where she dodged questions about the Nightcrawler star, saying, "I'm always optimistic about love."

One month later, the couple went for a stroll through New York City while visiting his sister, Maggie Gyllenhaal, for Thanksgiving. In December 2020, the Crazy Heart star told Us Weekly that it was "great" having Swift over for dinner.

When, Swift and the Tony winner called it quits ahead of January 2011, a source told Us at the time, "Jake just told her it wasn't working out. Taylor is really upset and hurt. She feels really burned by him."

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The ‘Red’ Release

The original version of Red dropped in 2012, At the time, fans were convinced the songs were about the Nocturnal Animals star, specifically "All Too Well," as Swift sings about a road trip to upstate New York and losing a scarf.

"Left my scarf there at your sister's house / And you've still got it in your drawer even now," the lyrics read, which some connected to the accessory she wore while with Jake over Thanksgiving in 2010.

Swift also included the lyrics, "Now you mail back my things and I walk home alone, But you keep my old scarf from that very first week  / 'Cause it reminds you of innocence and it smells like me."

Through the years, the California native has been photographed wearing a scarf that looks identical to Swift's. During a 2017 appearance on Watch What Happens Live with Andy Cohen, his sister responded to the rumors that the "Bad Blood" singer's belongings may still be in her home, telling the host, “I never understood why everybody asked me about this scarf. I am in the dark about the scarf. It’s totally possible, I don’t know.”

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The Subtle Mentions

The exes have discussed their breakup and the subsequent shady songs over the years — but not in depth. Three years after the album's release, Jake was asked about the song "All Too Well" during an interview on The Howard Stern Show.

"Do I [have a song]? I don't know," the actor coyly replied in 2015, referring to Swift at the time as a "beautiful girl."

In March 2021, the Miss Americana star teased a new version of her “Wildest Dreams” track in the most unlikely of places — a trailer for Jake's movie Spirit Untamed.

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The Walk Down Memory Lane

"Musically and lyrically, Red resembled a heartbroken person. It was all over the place, a fractured mosaic of feelings that somehow all fit together in the end," the singer wrote via Instagram in June 2021, confirming that an updated version of Red was on the way. "Happy, free, confused, lonely, devastated, euphoric, wild, and tortured by memories past. Like trying on pieces of a new life, I went into the studio and experimented with different sounds and collaborators."

At the time, Swift teased that "All Too Well" would be released in its full 10-minute glory, later announcing a short film starring Sadie Sink and Dylan O'Brien to go along with it. Some fans were quick to point out that the Stranger Things star and the Teen Wolf alum's ages line up with how old Swift and Jake were during their relationship.

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The New Version

In November 2021, Swift released the full 10-minute version of her iconic breakup anthem "All Too Well," including more details about her split from Gyllenhaal than ever.

"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," she sings.

Later on, she confirms the romance was only a few months long, saying, "And I was thinking on the drive down / Any time now, he's gonna say it's love / You never called it what it was / Til we were dead and gone and buried / Check the pulse and come back / Swearing it's the same / After three months in the grave."

She even references an "unnamed actress" finding her crying at a party – and fans were convinced it was Jennifer Aniston, who reportedly offered Swift dating advice in 2011.

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Their Current Status

The actor simply replied no when Esquire asked him in February 2022 whether he had listened to Red (Taylor’s Version). He went on to open up about social media attention.

“At some point, I think it’s important when supporters get unruly that we feel a responsibility to have them be civil and not allow for cyberbullying in one’s name,” Gyllenhaal told the magazine. “That begs for a deeper philosophical question. Not about any individual, per se, but a conversation that allows us to examine how we can—or should, even—take responsibility for what we put into the world, our contributions into the world. How do we provoke a conversation? We see that in politics. There’s anger and divisiveness, and it’s literally life-threatening in the extreme.”

When it came to the song, specifically, however, he said he didn’t hold a grudge. “It has nothing to do with me. It’s about her relationship with her fans,” he said. “It is her expression. Artists tap into personal experiences for inspiration, and I don’t begrudge anyone that."