All Too Swift

On Taylor Swift’s “All Too Well”…

M.G. Siegler
500ish
Published in
7 min readNov 20, 2021

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If you spent anytime on Twitter last week, you undoubtedly saw people tweeting non-stop about Taylor Swift. I find that this happens with good regularity regardless of whom you may follow. Any news around her tends to flood the social zones, and there’s often news about her. Much of it seems extremely smart on her part. And last week was no different as she lit Twitter aflame by releasing a re-recorded version of her 2012 album, Red.

Continuing her awesomely vindictive and extremely savvy plot to recreate all of the albums which she doesn’t fully own and have seen their rights traded like baseball cards amongst bidders who don’t care about baseball,¹ Red (Taylor’s Version) is clearly already a triumph. But one song on the album stands above both in terms of buzz and beauty. And it’s 10 minutes long.

Before diving into it, I should note that while I like Taylor Swift’s music in so far that any red-blooded consumer who hears it on the radio might,² I’m not like some diehard fan. I did very much like her album Folklore, which just seemed like perfect place, perfect time, perfect mood for the world wrapped in a pandemic. I never would have expected Taylor Swift and Bon Iver and The National to be a musical match, but I was wrong. Very wrong! Anyway, all of this is to say that I don’t think I had ever even heard the original version of “All Too Well”.³ If I have, it was in passing and I didn’t recall it. But as the internet blew up thanks to her performance of the again, 10 minute version on Saturday Night Live last week,⁴ I felt socially obligated to give it a listen.

And — shocker — it’s really good. But I like it in ways I didn’t fully expect.

First and foremost, you hear it (and watch the performance) and you think: wow, someone really broke this woman’s heart. But what’s unique about this song, at least as much as any other breakup song — of which Taylor Swift is the undisputed master, more on that in a bit — is that you can actually know the backstory here. If not the full thing in that you didn’t live it yourself, the high level of it since it played out in public. And while humorously neither party has full-on confirmed the background nature of the song, if it wasn’t obvious before, the 10-minute video Swift commissioned for the new version makes it even more clear. The bearded beanie guy that Dylan O’Brien is playing is his fellow actor Jake Gyllenhaal.⁵

Here’s where I’ll admit the sort of embarrassing rabbit hole I went down trying to figure out the backstory. Again, it’s not hard to figure out and there’s a lot of content on the topic, but the fact that I, as a 40-year-old man, was spending time on this is… not something I thought I would be doing as a 40-year-old man! But hey, the little one was down to sleep and my wife was out of town. Rabbit holes are dug for moments like this.

Anyway, as I read about the Swift/Gyllenhaal relationship, the first thing that struck me was how short it was. Seemingly just a few months. And that led to my initial reaction that this perhaps feels a bit unfair to Jake — especially since he’s now gotten dragged not once, but twice, through this mud. A decade apart! Most people move on, Taylor has not. Or, that’s not fair, perhaps she has, but for whatever reason — again, maybe it’s as simple as being savvy and knowing how well it would play, quite literally — she decided to also literally double down here, with twice the song.

But then I start thinking to myself: I obviously have no idea who these people are. I’m just a guy sitting here watching this performance and reading some blogs and trying to extrapolate meaning from this song. This is dangerous territory from which to draw any sort of conclusions.

Listening to the song a few more times, I’m again struck by how good it is. And regardless of my qualifications on the actual relationship in question, I think it conveys powerful aspects for more or less every relationship. Certainly those in the early days. And that’s why I think it resonates so well. Even as a ten minute song about a three month relationship re-released a decade later.

To put it more directly: I think this may be the single best encapsulation of the early stages of a love affair that I’ve ever heard. It’s only with hindsight that you can have the perspective that maybe this wasn’t the greatest thing in the world, or meant to be. But in the moment, and especially right after the moment, the world stops. And this song captures that halt.

In some ways, this may be the ultimate break-up song.⁶ Because most relationships are not long. And so this captures a sentiment not only that can resonate with pretty much everyone, but that can resonate multiple times in peoples’ own minds and memories. I’ve lived some version of this. We’ve all lived some version of this. Again, in hindsight it’s easy to say that these moments in time don’t matter, but they certainly do in the moment. They matter more than anything. This is what life is all about. The time we spend with others and that others spend with us. We all move on. Because we have to. But the time was spent. And we wonder…

Another element of the song that comes with multiple listens: the left-behind scarf is the (clever) hook in and lead out, but it’s the age element that is clearly what burns here. Swift makes it clear that the relationship ended because Gyllenhaal said they were just too far apart in age (roughly ten years). This allows her to get in the fantastic Dazed and Confused-style dig that she’d imagine that while she’ll get older, his girlfriends will stay the same age — which, amazingly, turned out to be true. I mean, again, this is probably unfair. But at least right now, she’s not wrong! Call your shot!

But beyond the individuals here, the discrepancy is also clearly a backbone of the song. And it’s actually not really about age so much as it’s about life asymmetry. The fact that Gyllenhaal was 30 and Swift was 20 matters less because of the gap in years and far more because of her actual age there. And I don’t mean the proximity to being a teenager, it’s just that she’s far closer to the massive changes in life that happen each and every year than he is. Put another way, there’s a reason why 17 year olds don’t hang out with 7 year olds. It would be weird because it is weird. Because you’re so far apart in life experience at those stages. That ten year gap is not the same at all ages. Someone who is 50 dating someone who is 40 is not weird. Same with 40 and 30. But again, Jake and Taylor veer too close to this line where it is weird. Not nefariously, but naturally.

She doesn’t hate him because of the scarf, she hates him because he ruined her 21st birthday. She undoubtedly feels like she was taken advantage of. Not in a scandalous way but in a way that is nonetheless upsetting.

Lastly, as alluded to above, Swift is clearly the master of breakup songs. To the point where, while I often think about what drives artists to be successful over long periods of time (which most can’t sustain), she seems to have this natural fuel that she can turn to again and again. Like Michael Jordan or Tom Brady using each and every slight to continue to fuel them even after they’ve reached the top of their games.

Perhaps part of this stigma is because her relationships are so public and break into the cultural zeitgeist because they often involve other celebrities. Some might view some of this as almost calculating, but I look at this from the opposite way. It may be that because so many of the relationships are public, the only way to truly give herself closure is to write these songs about them. We all have our tools, her’s just happens to be extremely popular music.

My god, I’ve just written over 1,500 words about this song. But it’s that good! It captures a hell of a lot more than one relatively short failed romance. And it’s the easiest ten-minute listen of all time because it’s so fantastic narratively. It was already like a short film before there was a short film to accompany it.

All that being said, I’m still left with the desire to hear Gyllenhaal’s side of the story. It only seems fair. Perhaps he can use his own tools of the trade to respond, not unlike Spike Jonze creating Her in response to Sofia Coppola’s Lost in Translation — a film which is also clearly referenced in “All Too Well”, no less.⁷

¹ I mean my god, beyond the amazing maneuver of fucking over the people who fucked you over, it’s a rather brilliant way to breathe new life into songs which people already know and love. This entire thing is smart on levels perhaps never seen nor heard before.

² And given that I don’t listen to the actual radio anymore, I would slot in something like “via algorithms on streaming services” or more likely “in pop culture”.

³ In hindsight in my “research” I know this is strange as it’s a hugely popular and awarded song. But I’m not lying. I wasn’t aware of it, which makes all of this all the more powerful!

⁴ Her seemingly selective use of looking directly at the camera in this performance is something else!

⁵ As a complete aside, kudos to Jake (and Maggie!) Gyllenhaal for not changing their names, Hollywood-style, despite them being nearly impossible to spell on first try no matter what you do — just remember, two ‘Ls’ to ‘As’!

⁶ I sort of can’t believe that the person who wrote this was in her early 20s. Then again, when you are young, they assume you know nothing…

⁷ This is another situation where neither side will acknowledge the obvious here. But the Scarlett Johansson element would not be denied.

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Writer turned investor turned investor who writes. General Partner at GV. I blog to think.