From the beginning, fans speculated that the ballad was about Jake Gyllenhaal, whom Swift dated for three months beginning in October 2010, when he was 29 going on 30, and she was 20 going on 21. (Her 21st birthday, when her boyfriend is a no-show, is the crux of another Red track, “The Moment I Knew,” and is referenced in the new version of “All Too Well.”)
There are two key pieces of evidence tying the actor to this mythical song. First, in the paparazzi shots of Jake and Taylor heading to his sister Maggie’s house in Brooklyn, Taylor is wearing a striped scarf. “All Too Well” is held together by first Taylor leaving the scarf at her paramour’s sister’s house, and then said paramour holding onto it. Second, Swift is known for leaving hidden messages in her album’s notes—specifically, irregularly capitalized letters in the lyrics of each song that spell out messages. The one for “All Too Well,” was “MAPLE LATTES,” which Jake and Taylor were reported to have on their walk to Maggie Gyllenhaal’s house. (For what it’s worth, Maggie told Andy Cohen that, although everyone asks, she has no recollection of the scarf.)
When she announced that Red (Taylor’s Version) would be coming, Swift hinted that one of the songs would be 10 minutes long. Naturally, the fans went wild. “All Too Well” is a perfect breakup ballad, achingly sentimental and with one of Swift’s trademark song-making bridges holding it all together. Surrounded by my fellow Swift fans, it occurred to me that this trilogy—which made coupled-up people like me and Cameron briefly (and jokingly) long for the gut punch of a breakup—felt like a gift from Swift to all her lovesick fans, past or present, and permission to wallow.
Now onto Swift’s directorial debut: The short stars Sadie Sink, 19, as “her” and Dylan O’Brien, 30, as “him.” (Did you notice a pattern in their ages? Swift’s fans sure did.) After lingering on a quote from Pablo Neruda, “Love is so short, forgetting is so long,” we open on a beautiful autumnal road. Sink and O’Brien at the beginning of their relationship, walking into a cottage in the forest where Sink hangs up a red scarf. They montage through happy-couple activities: playing a card game, kissing in the forest, spontaneous piggy-backing. Then, part 2, titled “The First Break in the Glass.” O’Brien is hosting a dinner party where Sink is clearly uncomfortable. He drops her hand at dinner in front of his sophisticated, artsy friends. A fight ensues. Later, they break up. The film ends with a flash-forward to 13 years in the future. Sink is now Swift, reading an excerpt of her first novel All Too Well to a crowd of crying women. The camera goes outside, and we see O’Brien, wearing the red scarf Sink left at their cabin upstate. Fin.