All the Taylor Swift Songs That Were Probably Inspired by Jake Gyllenhaal

This is the first song fans associate with Jake Gyllenhaal and what sparked an entire lore around a scarf. Many consider "All Too Well" to be Swift's best song, as it captures the heartbreak and naivety of falling in love in your early 20s. It is filled with Swift's iconic prose and relies heavily on imagery. Fans are certain it's about Gyllenhaal, although Swift has never confirmed this.

The telling lyrics: "You used to be a little kid with glasses in a twin-sized bed / And your mother's telling stories 'bout you on the tee-ball team"; "And I left my scarf there at your sister's house"; "After plaid shirt days and nights when you made me your own"

Why? The lyric regarding a little kid with glasses is believed to reference a now-deleted Instagram post by Gyllenhaal of himself as a young child with glasses. He also discussed on "The Ellen Degeneres Show" that he likes to bring new dates to meet his mom, so it's likely Swift met her and heard these stories about him as a child. Meanwhile, the scarf has become a symbol of the "Red" era, and fans believe the sister in question is Maggie Gyllenhaal, who's also a prominent celebrity. Finally, Gyllenhaal is known for wearing plaid shirts, and during this time, Swift was also often spotted wearing plaid.

Swift once mentioned that the initial lyrics of fan-favorite "All Too Well" were more than 10 minutes long. This spurred fans to call for the release of the full version, and Swift granted this request on "Red (Taylor's Version)," which came out at the end of 2021. This is technically a different song from "All Too Well" because it includes many additional lyrics that seem to reference Gyllenhaal.

The telling lyrics: "Sippin' coffee like you're on a late-night show"; "And he said, 'It's supposed to be fun turning 21'"; "I'll get older, but your lovers stay my age / From when your Brooklyn broke my skin and bones"

Why? Swift compares her lover meeting her father for coffee to how he'd act on a late-night show, which actors like Gyllenhaal often appear on. She references a disastrous 21st birthday party where her boyfriend never turned up, and Swift turned 21 during their relationship (her birthday is on Dec. 13, and they broke up sometime around New Year's). The age difference between Swift and Gyllenhaal (21 and 30) was often cited as a reason for the breakup, but his next partners were similarly young. Finally, Gyllenhaal notably lived in Brooklyn during their relationship, and the pair were often spotted out and about there. Most specifically, it was reported Swift celebrated Thanksgiving there with his family.

Released as a vault track on "Red (Taylor's Version)" in 2021, "I Bet You Think About Me" was accompanied by a music video directed by Swift's long-time BFF Blake Lively. The song sounds like a return to Swift's country roots and is a fun play on how she's always been labeled the obsessive one, as she ponders how often her ex-partner must think about her. Given that you can't escape Swift and her music anywhere you go in the world, he probably can't help but think about her a lot!

The telling lyrics: "You grew up in a silver-spoon gated community. Glamorous, shiny, bright Beverly Hills"; "Well, I tried to fit in with your upper-crust circles"; "At your cool indie music concerts every week"; "With your organic shoes and your million-dollar couch"

Why? Gyllenhaal grew up in Los Angeles, coming from a wealthy family deeply connected to the movie industry (his godmother is Jamie Lee Curtis). He was nine years older than Swift, so it's unsurprising that she felt out of place in his friend groups, especially given that she was a young pop star. Gyllenhaal has publicly cited his love for indie music, which Swift also mentions in songs like "We Are Never Getting Back Together." There aren't too many of Swift's exes who could afford a million-dollar couch, but a successful actor like Gyllenhaal most certainly could.

There's a moment in every failed relationship when you know with certainty that this isn't going to work, and that epiphany is what makes "The Moment I Knew" such a heartbreaking track on Swift's "Red" album. It covers that disastrous 21st birthday party, which Gyllenhaal seemingly did not attend, if her lyrics are anything to go by, and how this was a final straw in the relationship.

The telling lyrics: "And they're all standing around me, singing 'Happy birthday to you'"; "How you said you'd be here"; "Christmas lights glisten"

Why? Swift's birthday is in December, which explains the Christmas lights hanging, and it's been confirmed that she and Gyllenhaal dated during this period. Similarly, it draws upon the broken promises mentioned in other songs presumably about her relationship with him and how the relationship was coming to a close, as it did just weeks later.

This energetic pop-rock track opens the "Red" album and takes a fairly optimistic view of love — a contrast to the rest of this breakup album. It depicts the thrill and free-falling feeling of tumbling into a new relationship. However, it also sneaks in mentions of some red flags she's ignoring as she falls in love with this new partner.

The telling lyrics: "Just twin fire signs, four blue eyes"; "This is the golden age"; "You're my Achilles heel"

Why? Gyllenhaal is the only known ex of Swift to be a fellow Sagittarius, which the line "twin fire signs" is seemingly in reference to. He also has big baby blues, just like Swift! The "Golden Age" most commonly refers to a period in Hollywood that was known for its glamour but also covering up a lot of abuse of young stars. Gyllenhaal is also an actor, which may explain the reference to Hollywood. Throughout the song, Swift drops hints that there's trouble to come in the relationship, such as how he is her "Achilles heel," which means he's her greatest weakness and will eventually be her demise.

This might be one of Swift's biggest hits, and the one most non-fans can name or even sing along to. "We Are Never Getting Back Together" follows Swift through a tumultuous relationship, where she and her partner keep breaking up and getting back together. The accompanying music video is just as popular and was shot in one take!

The telling lyrics: "With some indie record that's much cooler than mine"

Why? Similarly to "I Bet You Think About Me," Swift seemingly references Gyllenhaal's known love for indie music and has spoken about how the relationship led her to feel like her music wasn't good enough. More presumed references to Gyllenhaal can be found in the iconic music video. There's a stuffed rabbit, which could symbolize his famous role in "Donnie Darko." Swift puts a scarf away, which might reference the scarf she was often photographed wearing when out with Gyllenhaal and the iconic scarf lyric in "All Too Well." Eagle-eyed fans also spotted a jar of apples on the TV, which might symbolize a famous apple-picking date that the pair went on in upstate New York.

Just when you think "Red" can't get any more heartbreaking, "I Almost Do" comes up. This song pulls upon Swift's country roots and covers the period following a breakup when you have the urge to reach out to your ex.

The telling lyrics: "Looking out at the city, and I bet"; "That I can't say hello to you and risk another goodbye"

Why? If this song is about Gyllenhaal, it has fewer direct references to him than some of the other songs on this list. But it follows similar themes as songs more obviously linked to him, like "We Are Never Getting Back Together" and "I Bet You Think About Me." Swift sings about looking out at the same city (both are known residents of New York and spent the majority of their relationship exploring the city together). Additionally, Swift mentions the risk of "another goodbye," and the pair were known to be on-again, off-again.

Finally, a Swift song presumed to be about Gyllenhaal that's not on the album "Red." However, this song's link to him revolves around its synonyms for the color red and how that album was seemingly mainly about him. Appearing on "Midnights," the song "Maroon" portrays a more grown-up love story, with more complexities and honesty than her previous songs.

The telling lyrics: "We were cleaning incense off your vinyl shelf"; "The one I was dancing with in New York, no shoes"; "The mark you left on my collarbone"

Why? Considering Gyllenhaal's interest in indie music, it isn't a huge leap to assume Swift is alluding to him when she references a "vinyl shelf." The majority of their romance took place in New York, and this is where Gyllenhaal still resides. Meanwhile, the mention of a mark on her collarbone may be a subtle reference to the iconic scarf in "All Too Well," which Swift has labeled a metaphor rather than an actual scarf. Throughout the song, there are synonyms for the color red, including maroon, scarlet, rust, blood, and burgundy. This likely refers to the album "Red," which is most commonly linked to Gyllenhaal, and the elaborate synonyms suggest she's looking at their romance with more maturity and wisdom.