The Relationships
Taylor Swift’s music is deeply autobiographical, showing that fame doesn’t shield anyone from real emotions. That’s why her songs feel so relatable.
Swift has always said she never confirms who inspires her lyrics. Even when details seem connected to real life, we can’t know whether a song reflects one person or a blend of memories and feelings. The fans don’t even always agree on who is or is not an inspiration for a song, it’s all just feelings.
Still, understanding the relationship timelines can add another layer to her work.
Let’s dive in.
Joe Jonas
July - October 2008
Young Love
From July to October 2008, Taylor Swift (18) and Joe Jonas (19) had a brief, intense young romance that fueled several early autobiographical songs. Swift later told Ellen that the breakup came via a 30-second voicemail—classic teen drama, but real feelings.
In the years since, they’ve remained friendly. They’ve attended each other’s shows, and Swift reportedly sent a gift to Jonas and Sophie Turner when their first child was born in 2020, a moment echoed in folklore’s “Invisible String.”
Fearless (2009) -Fearless
Fearless (2009)- Forever & Always
Speak Now (2010) - Last Kiss
Fearless (Taylor’s Version) (2021) - You All Over Me
Fearless (Taylor’s Version) (2021) - Mr. Perfectly Fine
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Much Better - The Jonas Brothers (2009)
While the original lyrics reference “Now I'm done with superstars / And all the tears on her guitar” he’s later changed it to “Now I’m cool with superstars”
Adam Young
The Crush
When Taylor Swift met Adam Young of Owl City, she was immediately “enchanted,” and he later said he felt the same. She used the word “wonderstruck” in the lyrics as a personal nod to him and even highlighted A D A M in the album booklet—a rare confirmation of her lyrical inspiration.
In 2011, Owl City released a response cover of “Enchanted” with lyrics directed back at her. They never dated, but their brief connection inspired one of Swift’s most beloved songs.
Taylor Lautner
July - December 2009
Better off Friends
They met on the 2009 set of the movie, “Valentine’s Day” and had a quiet relationship for a few months. While the relationship was not long-lived, the friendship carries on.
In 2023 when Swift released Speak Now Taylor’s Version, the music video for the vault track “I Can See You” featured Lautner. Lautner also attended the ERAs concert where the video was premiered. Both Swift and Lautner talk about their friendship that continues long after they dated.
Speak Now (2010) - Back to December
Speak Now (2023) - I Can See You (Music Video)
John Mayer
July - December 2009
The Boy They Warned You About
In November 2009, John Mayer released his album Battle Studies in which he and Swift worked together on the song “Half of My Heart”. At the time, he was 32 and Swift was 19. While they were only dating a few months, less than a year later in October of 2010 when Speak Now was released, it seemed clear Mayer had a lasting impact on Swift.
Some worthwhile observations that may unlock the lyrics further. John Mayer has brown eyes, is a self-confessed womanizer, loves chess, has a gap in his teeth (now corrected), tattoos, and a distinctive sound on the guitar, which many say are echoed in Swift’s song “Dear John”. At the time of them dating, Mayer also lived in a renovated church.
Speak Now (2010) - Sparks Fly
"Sparks Fly" is about falling for someone who you maybe shouldn't fall for, but you can't stop yourself because there's such a connection and chemistry- Taylor Swift
Speak Now (2010) - Superman
Speak Now (2010) - Ours
Speak Now (2010) - The Story Of Us
"The Story of Us" is a song that I wrote about an awkward situation where, well…This is about one of those situations where the strange place that I ran into him was an awards show.” - Taylor Swift
The line “The battle’s in your hands now/but I would lay my armor down” seems like a call back to Mayer’s album Battle Studies where they met
Speak Now (2010) - Dear John
“You should’ve known better.”
Midnights (2022) - Would’ve, Could’ve, Should’ve
Swift was 32 when she wrote this song, the same age Mayer had been when they were dating. Note that lyrics contain “would’ve” and “could’ve” but they do not contain “should’ve” -a call back to “Dear John”. The line “Years of tearing down our banners…” could once again be a call back to Mayer’s album, Battle Studies. The track is also 19th on the album, perhaps a wink at the age Swift was when the relationship occurred.
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Paper Doll - John Mayer (2013)
The song's lyric "you're like 22 girls in one," have been seen as a reference to both Taylor Swift's song "22" and potentially a criticism of her changing image. The “Dear John” lyric: “you paint me a blue sky then go back and turn it to rain” is often linked with Mayer’s lyric, “and if those angel wings don’t fly, someone’s going to paint you another sky.” Mayer has since denied its about Swift.
It Shouldn’t Matter but it Does - John Mayer (2021)
It includes the lyric “I shouldn't leave you messages in every little song.” and has three titles of Swift songs included (Mean, Clean, and Both of Us). The lyrics point out over and over it “shouldn’t matter”, and Swift’s WCS’s opening includes, “..did it matter?” Swift and Mayer’s paths may have crossed around this time period, possibly triggering Mayer to reminisce.
Harry Styles
November 2012 - January 2013
Fast, Bright, Gone
Taylor Swift and Harry Styles met at the Kids’ Choice Awards in March 2012 and crossed paths throughout the year. They went public that November and split by January 2013.
When 1989 arrived in late 2014, many tracks reflected the excitement, tension, and imbalance of a relationship where one person was far more committed than the other—widely linked to their brief romance.
Further observations include the pair exchanged paper airplane necklaces and were also involved in a snow mobile accident that left Styles requiring 20 stitches.
1989 (2014) - Style
Swift described it as being about a relationship that "never really done" and involves people who float in and out of each other's lives. The title of the song and describing Styles' "long hair, slicked back, white t-shirt" is clear.
1989 (2014) - Out of the Woods
This track details the anxiety Swift felt in their high-profile relationship.
1989 (2014) - I Know Places
The lyrics express anxiety, a desire for privacy, and the struggle of a love under constant pressure, where the couple must run and hide together to protect their relationship.
1989 (2014) - Clean
“‘Clean’ I wrote as I was walking out of Liberty in London. Someone I used to date — it hit me that I’d been in the same city as him for two weeks and I hadn’t thought about it,” Swift shared. “When it did hit me, it was like, ‘Oh, I hope he’s doing well.’ And nothing else.”
1989 (2014) - Wonderland
The song includes references to green eyes and a "Cheshire cat," a nod to Styles' hometown of Holmes Chapel in Cheshire, England.
Midnights (2022) - Question?
This song samples "Out of the Woods" and starts with the lyric, “I remember..” echoing “Out of the Woods”. It also references a New Year's Eve kiss, alluding to Dick Clark’s Rocking New Year’s Eve 2013. Both Styles and Swift attended the 2021 Grammy’s, perhaps inspiring all the questions Swift asks in the song.
1989 (Taylor’s Version) (2023) - Now That We Don’t Talk
1989 (Taylor’s Version) (2023) - Is It Over Now?
The lyrics “Whеn you lost control / Red blood, white snow” references the snow mobile accident the two had. "Blue dress on a boat," a nod to an infamous Jan. 2013 photo of her leaving a vacation with Harry after their rumored breakup.
1989 (Taylor’s Version) (2023) -Say Don’t Go
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Two Ghosts - Harry Styles (2017)
It’s widely speculated to be about Taylor Swift, due to shared lyrical references like "same lips red, same eyes blue" and "same white shirt" like in Swift’s “Style”. While Styles has never directly confirmed the song is about Swift, his awkward response when asked about it and the coincidental lyrical connections have fueled this fan theory.