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Things Worth Remembering: Taylor Swift’s Greatest Song
“A five-minute song for a six-week relationship? That struck me as verging on restrained,” writes Hadley Freeman. (Emma McIntyre/AMA2019/Getty Images for dcp)
She creates aural crack cocaine for people like me, whose favorite pastime is to drill sad songs into our brain on repeat.
By Hadley Freeman
10.05.25 — Things Worth Remembering
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Welcome to Things Worth Remembering, our weekly column in which writers share a few lines of poetry that all of us should commit to heart. This week we honor the most popular lyricist ever born (probably), Taylor Swift, whose new album landed on Friday. To mark the occasion, Hadley Freeman reflects on the greatest song Swift has ever written. Enjoy!

I think back on the first time I heard “All Too Well” with the kind of frisson that Luke Skywalker probably experiences when he remembers the first time he picked up his light saber—and if you’re thinking that movie reference suggests I’m definitely too old for a song about a 20-year-old whose heart has been broken, shut up.

It was 2012 and Red, Taylor Swift’s fourth album, had just been released. The fifth track, “All Too Well,” which wasn’t even released as a single (madness), tells the story of a love affair that ends with abrupt cruelty. But that really does not capture the cinematic magnificence of the song. The combination of that nostalgia-soaked tune and those Swiftian specific-yet-relatable lyrics—she left her scarf in his sister’s house! They danced round the kitchen to the refrigerator light!—instantly made it aural crack cocaine for people like me whose favorite pastime is to drill sad songs into our brain on repeat until we can no longer distinguish where the song ends and our actual life begins.


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“All Too Well” is like a mash-up of Bob Dylan’s “Visions of Johanna” with U2’s “With or Without You”—two canonical texts for us connoisseurs of sad songs—but with better lyrics than either. “And you call me up again just to break me like a promise / So casually cruel in the name of being honest”: I swear to God, the first time I heard that couplet—the concision! The precision!—my knees buckled. Do I need to add I was, at that time, heartbroken? We’ll get back to that.

So yes, I really liked the song. And when I found out the song was maybe-possibly-actually-yes-definitely about the actor Jake Gyllenhaal, who dumped Swift after about six weeks, I liked it even more. A five-minute song for a six-week relationship? That struck me as verging on restrained, although now is possibly the moment to mention that, at this point, I had recently moved from London to New York specifically to get over a relationship that had lasted—yes—six weeks.

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Hadley Freeman
Hadley Freeman is a columnist for The Sunday Times and author of Good Girls: A Story and Study of Anorexia. Follow her on X @HadleyFreeman.
Tags:
Taylor Swift
Love & Relationships
Music
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