Taylor And Jake’s Rumored Relationship Timeline Is Pretty Intense
Let’s unpack those three months.
Based on the 10-minute version of “All Too Well,” it sounds like Taylor Swift and Jake Gyllenhaal weren’t together for a long time or a good time. While neither star has ever spoken publicly about their rumored relationship — or even confirmed that they really were together — their reportedly tense romance is widely assumed to be the inspiration for several songs on Red, including “All Too Well.”
Between the new lyrics and the corresponding short film, it appears that Swift is shedding new light on their former relationship. Throughout the searing track, Swift doesn’t paint her ex in the most flattering light. At one point in the song, she sings: “You said if we had been closer in age maybe it would have been fine / And that made me want to die / The idea you had of me, who was she? / A never-needy ever lovely jewel whose shine reflects on you.” Oof.
But what really went down between Swift and Gyllenhaal — if anything at all? A closer look at the timeline of the singer and The Guilty actor’s rumored relationship gives fans a sense of just how well art can imitate life. Their rumored romance was short-lived, but that doesn’t make it any less heartbreaking.
They Were First Spotted Together In October 2010
Swift and Gyllenhaal were first spotted together during a taping of Saturday Night Live in October 2010. (Does this feel full circle to anyone else — especially considering she recently performed her extended “All Too Well” on the SNL stage?)
At the time, a source told People, “They showed up together. They walked around together backstage, but they were careful not to be seen too close. It was hard to tell if they were together, but everyone was shocked that she brought him.”
They actually met before SNL. The duo was first set up by Gwyneth Paltrow, who hosted Swift and Gyllenhaal at a dinner party. In Dec. 2010, Paltrow told USA Today that she had taken on the role of matchmaker. “I've just known Jake for a long time and he's a great guy. And Chris [Martin] has a friendship with Taylor,” she explained.
They Reportedly Spent Thanksgiving Together In November 2010
Swift and Gyllenhaal’s relationship progressed pretty quickly after that. Only a month into their romance, he reportedly brought Swift to his sister Maggie Gyllenhaal’s house for Thanksgiving. At the time, an Us Weekly source claimed, “[Swift] loves his family and he loves hers.”
And this might be when that famous scarf went missing. During an interview with Andy Cohen on Watch What Happens Live in 2017, Maggie admitted that it was “possible” that she still had Swift’s scarf. “I am in the dark about the scarf. It’s totally possible. I don’t know.”
Swift Turned 21 On Dec. 13, 2010 (And Gyllenhaal Reportedly Missed It)
Swift and Gyllenhaal were reportedly still in a relationship when she turned 21, but if you take her lyrics as fact, things had turned slightly sour. In the 10-minute version of “All Too Well,” she describes a sad conversation with her dad on her birthday: “But then he watched me watch the front door all night, willing you to come / And he said, ‘It's supposed to be fun turning twenty-one.’” Was Gyllenhaal a no-show?
“The Moment I Knew,” another Red track, also describes her boyfriend missing her birthday party. On that track, Swift pinpoints that moment as the beginning of the end: “You called me later / And said, ‘I’m sorry, I didn’t make it’ / And I said, ‘I’m sorry, too’ / And that was the moment I knew.”
They Reportedly Broke Up In Jan. 2011
By the new year, Swift and Gyllenhaal’s romance had fizzled. “Jake reached out to her and started all of this, but now he’s not acting as interested,” a source claimed to Us at the time. “He said he wasn't feeling it anymore and was uncomfortable with all the attention they got.”
Apparently, their age difference played a role in their split. (When they met, Swift was 20 and Gyllenhaal was 29.) “He also said he could feel the age difference. Taylor is really upset. We told her not to move so fast with this but she didn't listen,” the source claimed. Oof.
The newly released “All Too Well” lyrics also point to an ill-fated age gap: “You said if we had been closer in age, maybe it would’ve been fine ... And I was never good at tellin’ jokes, but the punchline goes/I’ll get older, but your lovers stay my age.” (Jeanne Cadieu, Gyllenhaal’s girlfriend of three years, is 25.)
There Was A ~Maybe~ Reconciliation In March 2011
In “All Too Well,” Swift mentions a potential reconciliation with the ex who inspired the song. So if the song really is about Gyllenhaal (and basically every sign points to that), he may have returned to Swift three months after their split to say “I love you” for the first time and attempt a reconciliation.
In the 10-minute song, Swift sings, “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.” (Is anyone else thinking about “We Are Never Getting Back Together” RN?!)
Though Swift has yet to confirm if this conversation actually happened IRL, in 2013, she did tell Vulture in her ex reached out about the Red album. At the time, she explained, “I heard from the guy that most of Red is about. 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.’” Not exactly a love confession, but still.
Truth is, we’ll probably never know exactly what went down between Swift and Gyllenhaal — yes, even though Swift’s All Too Well: The Short Film seemingly broke down their relationship into seven convenient parts: An Upstate Escape, The First Crack In The Glass, Are You Real?, The Breaking Point, The Reeling, The Remembering, and Thirteen Years Gone By.
All in all, their relationship timeline prompts more questions than answers (like, seriously, where is the scarf, Maggie?). Still, Taylor’s Version of events is — at the very least — very catchy, even if it is mostly speculation for now.
