From calling out Joe Jonas on “Mr. Perfectly Fine” and “Forever and Always” to her Harry Styles nods in “Style,” Taylor Swift is known for not holding back on her breakup songs. The ex who has been in question the longest is probably Jake Gyllenhaal, with their shared past resurfacing by way of the 10-minute version of "All Too Well" on Swift's re-released version of Red. The rumors have swirled around this song for years, but after the release of the short film All Too Well and the way Swift stammered through an interview question at the Toronto International Film Festival, some long-standing fan theories about a certain scarf appear to be closer to truth than ever.
In the song, Swift mentions the scarf that fans have long obsessed over with speculation that it could metaphorically represent the singer losing her virginity to Gyllenhaal. Then, when the singer released her short film, said scarf became an even bigger part of the narrative. The female in the video for "All Too Well", portayed by Sadie Sink, leaves the scarf in the house of a man played by Dylan O’Brien, and when the scarf is shown again in the end, O’Brien’s character is wearing it while looking through a window at Sink’s character, after the two had broken up.
A few months after the short film's release, and a few weeks after its win at the VMA’s, Swift screened it at TIFF and then took part in a Q&A discussion about the making of it. When asked directly what the scarf stood for, the Grammy queen had a very awkward reaction.
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All these ums are not typical for a Swift answer. She is well-spoken and typically gives confident and well-worded responses. The fact that she fumbled quite a bit over her words to create an overall awkward answer seems to allude to the fact that this song is centered around a sensitive subject.
To shed some light on a possible reason for the awkward response: back in 2014, a source told Radar Online that Swift had lost her virginity to Gyllenhaal. Not long after, she celebrated her 21 birthday party, which the Donnie Darko actor did not attend, reportedly leaving her devastated. A party similar to this is depicted in the All Too Well short film, which made fans even more confident that the metaphor of the scarf is in fact about her losing her virginity.
It’s fairly obvious that the song is depicting Swift and Gyllenhaals’ relationship. Swift has admitted that Red is her “only true break-up album” and fans were quick to call out Gyllenhaal.
The two dated when Swift was 20 and Gyllenhaal was 29. As for the actors in the video the age gap matches. O’Brien is 31 and Sink is 20. Further confirmation about who the song is about came when Gyllenhaal commented on the video, saying he does not “begrudge” Swift for using her personal experience in her art.
Though the rumors continue to swirl, both the All Too Well singer and the Nightcrawler actor have moved on. Swift has been in a relationship with actor Joe Alwyn for years, and they’re still happily together, as seen when they were caught being cute at the VMA’s a few weeks ago. She also announced her new album Midnights and wrote an original song for Where The Crawdad’s Sing, as well as re-released her song “False God” for The Summer I Turned Pretty, which can be watched with an Amazon Prime subscription.
So, while things may not have been all too well back then, and may be all too awkward right now, fans' attention and speculation will likely shift, especially with Swift's new album coming out soon. Which will no doubt lead to new swaths of clue-seeking and detective work.
Riley Utley is a Weekend Editor at CinemaBlend. She spent many years working in local journalism across the country writing about art, news and sports. One of her favorite films is When Harry Met Sally and she walks around constantly quoting Ted Lasso.
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