Taylor Swift’s boyfriends: Everything we know about her dating history | Joe Jonas, Taylor Lautner, John Mayer, Joe Alwyn, Travis Kelce and more


Take a deep breath, because this one’s a tough pill to swallow.

Taylor Swift and Jake Gyllenhaal met in 2010 and were quickly snapped walking through New York City and even attending Thanksgiving together. 

Shortly after this, the two split and Swift released the album Red, which featured a number of heartbreaking songs which were rumoured to be about the actor.

This speculation was all but confirmed on November 12, 2021 when she re-released the album with a ten minute version of All Too Well, which she reportedly wrote following their breakup in 2011. The song had been hidden in Swift’s vault all these years, with fans only hearing it for the first time now. 

Swift previously spoke about another track off the album, The Last Time –again said to be about Gyllenhaal. The singer explained it was about an “experience I had with someone who was kind of this unreliable guy. You never know when he’s going to leave, you never know when he’s going to come back, but he always does come back,” she said in an interview with NPR in 2012.

Similarly, in the bonus the track Would’ve, Could’ve, Should’ve off Midnights, the line:

“Give me back my girlhood, it was mine first.”

is also speculated to be about Gyllenhaal, with whom she shared a nine-year age gap with.


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