Taylor Swift’s Most Popular Songs About Jake Gyllenhaal


Like many of his other romances, both short and long, Taylor Swift has sung about actor Jake Gyllenhaal several times in the past. It is believed that there are quite a few songs about their dating, which lasted from late 2010 to early 2011.

Composite image of Taylor Swift and Jake Gyllenhaal
L: Taylor Swift in November 2010 | Andrew H. Walker / Getty Images for IMC, R: Jake Gyllenhaal in November 2010 | Jon Kopaloff / FilmMagic

Although the timeline is a bit confusing, and the two were very secretive about their relationship, fans of the singer (who are called Swifties) have identified which of her hits relate to Gyllenhaal. Here are five of them that were charted on the Billboard Hot 100.

‘We never never never get back together’

Swift’s first single from her 2012 album Red It was titled “We’ll Never Be Together Again”, the song was a massive hit, peaking at number 1 and spending 24 weeks on the Billboard Hot 100 chart. It was her first number 1 single and, what’s more, she ranked first during several weeks.

On the track, Swift sings about someone she broke up with and came back with a few times. She explained in a webcast (as reported by ABC) that she conceived the concept after sharing details of a recent relationship in 2011.

‘Red’

RELATED: Taylor Swift Fans Celebrate 7 Years of ‘Red’

The album’s title track was finally released as their fifth and final single. But before that, it entered country music radio and was available for purchase as a promotional single. “Red” spent 22 weeks on the Billboard chart, reaching number 6.

Swift didn’t go into much describing this song, he just told ABC Good morning america that she “wrote this song about the fact that some things are hard to forget because the emotions involved with them were so intense.” However, the track of the album notes was “SAG”, as in Screen Actors Guild, or Gyllenhaal’s astrological sign, Sagittarius.

‘State of grace’

Speaking of astrology, that was also the clue as to who the “State of Grace” is all about. On the first track in RedSwift sings about falling in love with someone new and his power. The letters “twin fire signs and four blue eyes” clearly indicate Gyllenhaal, as the exes have birthdays in mid-December.

“State of Grace” was released as the fourth promotional single and the fourth official single. Red. However, it didn’t perform as well as other singles, spending just a week on the chart at number 13.

‘All too well’

Is Red The track wasn’t one, but it has become a Swifties’ favorite over time. The artist performed “All Too Well” at the 2014 Grammy Awards, and played it on subsequent tours. Due to the fans’ love for the song, he managed to sneak onto the list for just a week, reaching number 80.

Again speaking to Good Morning America on ABC, Swift said it was “the hardest thing to write” on Red. This was because it was initially 10 minutes long, so it obviously had a lot to say. The track’s fall theme, along with the note track, all point directly to Gyllenhaal.

‘The moment I knew’

Finally, “The Moment I Knew” is a song from the deluxe version of Red. Due to this, it is a little less commented, although it was a promotional single. And Swifties managed to make the list for a week, landing at number 64 on the Billboard Hot 100.

Talking to Yahoo! Music, Swift said, “It was a song about my 21st birthday party, which was the worst experience of my life.” Swift sings that her partner did not attend the event, and it was then that she knew it was all over. She turned 21 in December 2010, which aligns with Gyllenhaal.