All Taylor Swift Songs About Jake Gyllenhaal (Or Rumored To Be)

If you’ve paid attention to Taylor Swift over the years, you probably know that towards the end of 2010, she was in a relationship with Jake Gyllenhaal until the beginning of 2011. She is known to write tracks about her ex-boyfriends and relationships, so when they broke up, she wrote material about him, specifically, on her Red album.

We’re going to tell you all Taylor Swift songs about Jake Gyllenhaal, or at least tracks rumored to be about him, so keep reading to learn more about those songs!

1. All Too Well 

The first song on our list rumored to be about Gyllenhaal that Swift wrote is All Too Well. This was originally released in 2012 on Red, and out of all of the tracks on our list, it is quite easily the biggest song from this album.

When you look at the lyrics of the track, you can tell that it’s a song detailing her time with him such as “And you call me up again, Just to break me like a promise, So casually cruel in the name of being honest.”

The lyrics are gut-wrenching and seem to go into detail about her life after the breakup with him, including putting in enough events to make it a story. She herself said All Too Well was the hardest track for her to write, not only because it’s so personal, but because there was so much she wanted to say but had trouble cutting down the song to be short enough for an album. 

February 9, 2012 – Jake Gyllenhaal at the 62nd Berlin International Film Festival. Image source: Siebbi, CC BY 3.0, via Wikimedia Commons

She would eventually say that the initial version of the track was around 10 minutes long, as opposed to the five minutes on the album version, and it was much more detailed and lyrically explicit. While this particular song was never released as a single, it’s the biggest hit from the album since it details the devastating breakup between her and him and goes into realizing those good times are long gone, and it tore her up more than any other relationship she’d had before.

2. All Too Well (10 minute version) 

Taylor Swift - All Too Well: The Short Film

In 2021, Swift released All Too Well (Taylor’s Version), which was the extended release of All Too Well, and we finally get the original 10-minute version of the song she initially wrote to begin with. In this extended track, we get to hear all of the lyrics that were cut from the original album version, and there’s no doubt in this one that it’s about Gyllenhaal.

The 10-minute song goes into even more detail about what happened between her and him, so there is no doubt who this track was really about. There is mention of her 21st birthday in the song and the fact that he didn’t show up to the party, with her dad noticing she was watching the door waiting for him to walk in and he never showed up.

The lyric “You said if we had been close in age, maybe it would have been fine,” and a little later, she reveals that the guy broke up with her because of her age, which is what happened with him since he thought the age gap was too much. 

The age gap between her and the guy is mentioned more than once in the song, which he used as his excuse to break up with her, but he dated other women after her that was her age or close to it, so it hurt her even more.

February 9, 2017 – Maggie Gyllenhaal at Berlinale. Image source: Maximilian Bühn, CC-BY-SA 4.0, CC BY-SA 4.0, via Wikimedia Commons

In this 10-minute version, a sister is also mentioned, so it’s obvious that she is Maggie Gyllenhaal. There were also parts of the music video that made it clear the track was about him because reenactments of situations between them were a part of the music video, such as when the paparazzi happened to film certain moments between the two of them. 

The actors from the music video are also about the age of Swift and Gyllenhaal at the time, with him being nearly 30 and her not yet 21 when they started dating. This 10-minute version leaves no doubt at all that the guy she’s talking about is him, and this song will be the track that she is remembered for when she dies because it’s that deep and that personal. It was so personal to her that it took her years to finally openly and publicly sing about it and put him on blast. 

3. The Moment I Knew 

Taylor Swift - The Moment I Knew (Taylor's Version) (Lyric Video)

The Moment I Knew stands out as being definitely about Gyllenhaal because that same birthday part is mentioned once again. The lyrics say “And there in the bathroom, I try not to fall apart, And the sinking feeling starts.” When you read that and know the story of him not coming to her 21st birthday party, then it’s easy to figure out it’s about him. 

Her birthday is December 13, so in the song when she mentions the door being decorated with Christmas lights, you get another confirmation she’s talking about her birthday party since it’s so close to Christmas.

June 5, 2010 – Taylor Swift performing during her concert in Foxboro, Massachusetts, as part of her Fearless Tour. Image source: Mealtedheadaches, CC BY-SA 2.0, via Wikimedia Commons

This track details her knowing the moment it was over between her and him, which is when he missed her 21st birthday party, and how she kept waiting for him to show up but he never did. The party incident is one of the most telling, and this is something she has brought up more than once, which shows just how much that particular situation hurt her at the time. 

They did split up in December, and while we don’t know the date specifically, it’s clear that she broke up with the person in the song in December given the title is The Moment I Knew. When you hear the ending to the track where the ex is calling her trying to apologize for not being at the party, and she cries in the bathroom because she knows it is over at that moment, it further hits home that this is all referencing him and that being what made her realize he was done with her.

4. I Bet You Think About Me

Taylor Swift ft. Chris Stapleton - I Bet You Think About Me (Taylor's Version) (Officia...

The next song we believe is about Gyllenhaal is Swift’s song I Bet You Think About Me, which features country music star Chris Stapleton. This track was not released on the original Red album since it was cut from it, but when she re-released Red (Taylor’s Version), she added this song as a bonus track, or from what she called “ From The Vault,” which were unreleased songs. 

I Bet You Think About Me is a country-pop track that we can assume was about Gyllenhaal because it was cut from Red, which is all about him plus there are a couple of clues that key us into it is about him in the song. One of those clues is how she talks about the difference between her and her ex when it comes to their childhood and upbringing, with the Gyllenhaal family being more upper-class and her growing up on a farm and not having nearly the money or connections that his family did. 

October 22, 2015 – Jake Gyllenhaal at the Toronto International Film Festival. Image source: Gordon Correll, CC BY-SA 2.0, via Wikimedia Commons

She mentions in the track how she felt out of place around her ex’s family because of their different upbringing and how shallow it was that this all played into the breakup. She also never felt comfortable around his group of friends and that’s all mentioned in I Bet You Think Of Me. She talks about how she knows her ex still thinks about her, hence the title of the song, and how she knew he still wondered about what may have been between the two and what their life together would have been like had they not broken up.

5. State Of Grace 

Taylor Swift - State Of Grace (Taylor's Version) (Lyric Video)

The next song is State Of Grace, which appeared on the album Red, and this track is more about what it feels like when you first fall in love with someone. There are feelings of being scared, yet it’s thrilling, and you also feel free as you begin to realize the fact you’re in love. This song is thought to be about Gyllenhaal like almost all of the other tracks on Red, and there is an upbeat vibe to this song that conveys Swift’s feelings of this blossoming relationship. 

However, further into the track, she talks about how love makes her blind, and there were so many red flags that she ignored. She mentions how love is what makes her weak, and it’s this weakness that has caused her so much heartache. She begins describing trying to get herself back together after the breakup happens, which means trying to start over again, and the pain she feels during this experience. 

August 7, 2015 – Milky Way and Sagittarius seen from Mount Yakushi, Hida Mountains, Tateyama, Toyama, Japan. Image source: Alpsdake, CC BY-SA 4.0, via Wikimedia Commons

There is one lyric in particular that makes it almost clear she’s talking about Gyllenhaal, which is about how both of their eyes are blue and how they both share a zodiac sign. Her birthday is December 13 and his is December 19, so they both have the same sign, and they both have blue eyes as well. 

6. We Are Never Ever Getting Back Together 

Taylor Swift - We Are Never Ever Getting Back Together

We Are Never Ever Getting Back Together is one of the most popular songs from Red, and this track is definitely about Gyllenhaal when you look at the lyrics. There is talk in the lyrics about the guy loving indie music, and he is known to have quite the indie music collection. This person is also very snobby when it comes to his music, and he is known for that too.

Another indication that this is about him is that there is a scarf featured in the music video, which seems to be the same scarf that Swift talks about in her other hit song, All Too Well. There is a bracelet that he gave her that is seen in the video too, so it’s pretty easy to see this is about him. 

September 3, 2011 – Taylor Swift. Image source: Marcin Wichary from San Francisco, U.S.A., CC BY 2.0, via Wikimedia Commons

She said that this track was born when she happened to run into a friend who was a mutual friend of hers and the ex-boyfriend, and he said he heard they were getting back together. It shocked her because that was news to her, and this is where she got the idea for the song We Are Never Ever Getting Back Together.

Other indications this song is about him come from it talking about how the guy liked to promise things but then break his promises, picking fights with her, and just an overall feeling of volatility to the relationship, which fits her relationship with him. 

March 12, 2011 – Donnie Darko, or is it just me? Image source: Andrew Basterfield, CC BY-SA 2.0, via Wikimedia Commons

There is also the fact that there is a stuffed animal in the music video, a rabbit, and in the movie Donnie Darko, where he was the leading actor, there was a character named Frank The Rabbit, often referred to as just Frank. That one is one more sign that points in the direction of him without her specifically saying this is about him, and it’s hard to ignore all of these signs.

7. I Almost Do 

Taylor Swift - I Almost Do (Taylor's Version) (Lyric Video)

Another song from Red that everyone thinks is about Gyllenhaal, which was released before We Are Never Ever Getting Back Together, is I Almost Do. In this track, she talks about resisting the urge to contact her ex because she thinks about him, but knows it’s not a good idea to try to have a relationship with him again. Swift mentions how she was sorry that she ignored the attempts from the ex when he tried to reach out but says she just can’t emotionally deal with it going bad and going through that breakup again. 

While it’s not explicitly stating anywhere it’s about him, it’s not hard to figure out who she’s talking about since nearly the entire album is about him. There’s a part of her that misses him yet she is standing strong and not trying to get back with him. Another clue here is that she talks about her ex looking out and staring at the city, and we know he had homes in New York City and Los Angeles, so it would make sense. 

8. Maroon

Maroon is one song that is believed to be about Gyllenhaal because it’s similar to tracks from the Red album, even though this song was released on the new album Midnights. There are references in the track to wine that has been spilled on a shirt, which sort of is in line with the wine spilled on the dress she had talked about before. 

A lot of fans think it’s her more mature and adult view of her relationship with him since maroon is a darker color than red. The color could also be significant with her realizing that instead of being in pain and angry over him dumping her, this signifies growth on her end and realizing that this wasn’t the best relationship and looking at that time in her life differently. 

August 9, 2023 – Taylor Swift performing Vigilante Shit at the Eras Tour in Inglewood, California. Image source: Paolo V, CC BY 2.0, via Wikimedia Commons

Other lines from the song include how she talks about choosing him but eventually says “And I lost you,” and we know that she chose him and he was the one who ended it with her. When you look at All Too Well (Taylor’s Version), you can understand that, and it makes Maroon much more likely to be about him than anyone else.

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