7 Best Taylor Swift Songs About Jake Gyllenhaal

Jake Gyllenhaal is one of Taylor Swift’s most famous and infamous ex-boyfriends.

Although the relationship only lasted from October 2010 to the end of that year, it inspired Taylor to write many of the songs from her subsequent album Red about him. Here are those songs.

“I Bet You Think About Me,” featuring Chris Stapleton

Year: 2021

Taylor rarely comes out and specifically says whom a song is written about. Instead, she drops hints throughout a song’s lyrics, music videos, and album for her Swifties to find. As a result, we can never say 100% whom a song is about… but we can offer some pretty good guesses.

“I Bet You Think About Me” was released on Taylor’s version of the Red album in 2021, which Taylor re-recorded after her original Red recordings and much of her catalog, were sold out.

The album contained extra “vault” songs, songs that Taylor had wanted to add to the album originally but eventually had to cut. The bitter, country-inspired “I Bet You Think About Me” was one of these songs.

Because it’s on the Red re-release, it’s already safe to assume that “I Bet You Think About Me, just like most of the songs on the original album, is about Jake. But Taylor drops a few hints throughout the song that point to him as well.

Most significantly, she points out the differences between her upbringing and that of her ex. While Taylor downplays her childhood a little bit (yes, she did technically grow up on a farm, but it was a Christmas tree farm) and her family wasn’t exactly struggling, it was still a far cry from the life of the Gyllenhaals.

Jake grew up in Hollywood. His father is a director, his mother a screenwriter, and his sister, Maggie, is an award-winning actress, director, producer, and writer who has starred in acclaimed films like The Dark Knight and Crazy Heart.

“I Bet You Think of Me” details how Taylor never felt like she belonged in her ex’s upper-crust lifestyle and never really fit in with his friends.

While those differences were partially behind the breakup, Taylor goes on to say that those shallow reasons shouldn’t have overshadowed their true connection, and she knows her ex still wonders what could have been.

“The Moment I Knew”

Year: 2012, re-released 2021

“The Moment I Knew” is a heartbreaking, soul-filled ballad about the realization that a relationship has run its course. Taylor recalls the exact moment of no return: when her ex missed her birthday party.

Taylor creates vivid imagery in the song, recalling the Christmas lights that decorated the door she watched so carefully, waiting for her boyfriend to arrive.

That makes sense, as Taylor’s December 13th birthday is just a few weeks before Christmas. While we don’t know the exact date that Taylor and Jake called it quits, we do know that it was sometime in December as they broke up before the New Year.

To add insult to injury, Taylor’s birthday in 2010 would have been her 21st, a significant milestone. Instead of celebrating, she details how she spent the entire party waiting for her love to arrive and breaking down in tears in the bathroom when it was clear he wasn’t going to show up.

At the end of the song, Taylor tells us her ex called to apologize for missing the party, but at that point, she already had a sinking feeling the relationship was at its end. It was the moment she knew, and she and Jake would break up not long after.

“I Almost Do”

Year: 2012, re-released 2021

“I Almost Do” is another heartbreaking ballad from Red. With a slight throwback to Taylor’s country music days, the song takes place after the breakup has occurred and centers around fighting the urge to reach out to an ex for your sanity.

Taylor details how often she thinks about her ex and how much she wants to reach out, but despite this, she never does, knowing another attempt at the relationship would be just as messy as the first.

She apologizes for ignoring her ex’s attempts to reach out but acknowledges that she can’t emotionally handle having to say goodbye again.

While this song doesn’t offer as many clues about the muse as others on this list, it’s still a safe bet to assume it’s about Jake.

It precedes her hit single “We Are Never Ever Getting Back Together” on the Red album, showing the progression between missing her ex and the resolve to never reconcile.

Taylor also mentions that she can picture her ex staring out over the city; Jake has homes in both L.A. and New York City. 

“State of Grace”

Year: 2012, re-released 2021

“State of Grace” is the premier track on the Red album, and unlike the others on this list, it takes an optimistic view of love. It describes the thrilling, scary, and freeing feeling of tumbling head-first into love.

While the upbeat pop-rock melody details the overwhelming ecstasy of falling in love, there seem to be some “red” flags hiding beneath the surface.

Taylor describes her love as her Achilles’ heel, meaning he creates a weakness in her. She also details how the relationship is teaching her to live with pain, causing her to pick up the pieces of her broken heart.

In one line, Taylor offers important clues as to whom she’s singing about, mentioning that she and her love are the same zodiac sign and both have blue eyes.

Jake’s birthday is on December 19th, less than a week after Taylor’s, making them both Sagittarius. He, like Taylor, has blue eyes.

“We Are Never Ever Getting Back Together”

Year: 2012, re-released in 2021

“We Are Never Ever Getting Back Together” is one of Taylor Swift’s biggest hits. The catchy single debuted on the U.S. Billboard Hot 100 at number 72 but jumped to number one by the following week, which was one of the biggest jumps in the chart’s history.

Guinness World Records named it the “Fastest Selling Single in Digital History” in 2012.

The upbeat song describes a volatile relationship, in which her ex liked to pick fights, make promises that he couldn’t keep, and try to string her along. In an interview with ABC, Taylor explains that the song came about after she ran into a mutual friend, who said he had heard that Taylor and her ex may be getting back together.

At the time, she was in the studio with two other songwriters, who asked her about the situation. As Taylor recounted her relationship with her ex, the idea for the song was born.

Within the song, the biggest hint that alludes to Jake is the ex’s snobbish love of indie music. Jake is known for preferring indie music, making the song’s ultra-pop vibes even more amusing.

More hints are found in the music video, which includes the infamous scarf mentioned in “All Too Well” and even shows Taylor wearing a bracelet that Jake gave her.

As perhaps a final nod to the relationship, the music video prominently displays a stuffed rabbit, perhaps an homage to the chaotic character Jake played in Donnie Darko.   

“All Too Well”

Year: 2012, re-released in 2021

“All Too Well” was never a single, but it is one of the most well-known songs from Red. Taylor’s lyrical talent truly shines in this song, with heart-wrenching and relatable lyrics accented by some marvelous musical choices.

The song details post-breakup heartbreak as Taylor remembers the good times before being hit with the reality that those times are gone. It is a sad song that shows that her ability to function after the breakup is very limited and that she’s struggling with her life.

Through “All Too Well,” Taylor manages to capture the absolute devastation of her breakup, something she only manages to top in our next pick.

“All Too Well (10 Minute Version)”

Year: 2021

When fans heard that the original “All Too Well” was ten minutes long and had to be cut, they begged for Taylor to release the full version.

Re-releasing Red was her chance, and while Swifties had been salivating for this version, they were by no means prepared for the gut punch that was the full ten-minute song.

The original dropped hints that she was referring to Jake, but the new lyrics make it impossible to ignore. She mentions her 21st birthday, which as we know, occurred while she and Jake were dating. She mentions a sister a few times, likely referring to Maggie Gyllenhaal.

The new lyrics are also scathing toward her ex, particularly when he mentions that one of the reasons he cited for the breakup was their age difference.

Despite this, he continued to date women who are the age Taylor was at the time. When they dated, Jake would have been just about to turn 30 while Taylor had yet to turn 21.

She took it to the next level with the All Too Well: The Short Film which starred Sadie Sink from Stranger Things and Dylan O’Brien from Teen Wolf and The Maze Runner.

The two actors have roughly the same age gap as Taylor and Jake.

Taylor, who wrote and directed the short film, also had them reenact moments between her and Jake that had been caught by the paparazzi, making it impossible to deny that the song was written about Jake. The short film went on to win the 2022 Grammy for Best Music Video

Top Taylor Swift Songs About Jake Gyllenhaal, Final Thoughts

Taylor’s never been shy about writing songs that detail her experiences, both elating and heartbreaking.

While Jake Gyllenhaal did a number on her (there’s a reason he was the most hated person on the internet for a while after the release of Taylor’s Version of Red), their relationship gave fans some of the most emotional and iconic songs in her collection.

Taylor Swift has cemented herself as an American music icon, and part of that is the way she took her tumultuous relationship with Jake Gyllenhaal and turned it into music history.

Next, why not check out Taylor Swift’s best songs?