It’s no secret that Taylor Swift‘s love life has inspired her best songwriting and biggest hits! From elbow bumping with strangers and being Enchanted to meet them, to relationships tied by an Invisible String, let’s dial it back to the very beginning of her discography — and pick apart all the hidden meanings!

Drew Dunlap

Drew Dunlap was Tay Tay’s high school sweetheart, and according to her, they broke up after he left for college. She dedicated her smash hit Tim McGraw to him, which is the song that most Swifties claim as the first one they ever heard. A single that put her on the map!

Jacob Alford

Jacob Alford is the inspiration for one of Taylor’s angriest songs to date. Fans will know Picture To Burn is an iconic moment in her discography — one she ended up later changing the lyrics to because she wrote it in such a tempered frenzy! But was it justified? We mean, she says the guy left her for another girl… And then they ended up getting married! Oof!

Drew Hartwick

Drew Hartwick isn’t exactly an ex, but he held a special place in teenage Tay’s heart. She wrote her legendary song Teardrops on my Guitar after crushing on Drew for a while. Reports say he didn’t even know Taylor liked him until after the song came out, to which he ended up going over to her house and asking her on a date — but it was too little, too late. She declined him!

Sam Armstrong

Another early-life beau for Tay — and one she probably wants to forget. Sam Armstrong inspired the song Should’ve Said No, which the pop star wrote after he cheated on her. She got her revenge, though! In her CD booklet for her debut album Taylor Swift, she capitalized the letters S, A, and M in the lyrics. Ha!

Joe Jonas

Here’s where we get into the more famous exes of Taylor. Joe Jonas is an iconic one for all the wrong reasons — he broke up with her in that infamous 27 second phone call back in 2008! And even though these two are cool now, he inspired some of her biggest heartbreak ballads, including Forever & Always, Last Kiss, Mr. Perfectly Fine, and Holy Ground. It’s even rumored she wrote Better Than Revenge about his ex, Camila Belle! 

Taylor Lautner

Dubbed everyone’s “favorite” T-Swizzle ex, Taylor Lautner might’ve only been a part of her love life for three months in mid-2009, but was the inspiration behind what’s probably her most self-reflective song. Tay’s songs usually have a theme of her getting her heart broken, but this one was her breaking his heart. Back to December is a classic we have to listen to every December (and beyond)!

John Mayer

John Mayer is another infamous Taylor ex, who is remembered for all the wrong reasons after their four-month fling back in late 2009 and early 2010. Their age-gap relationship was messy and wild, and if you want to know ALL the details, just listen to these smash hits: Dear John, Ours, Superman, The Story Of Us, I Knew You Were Trouble, Would’ve Could’ve Should’ve.

Adam Young

While Owl City‘s singer Adam Young wasn’t an official boyfriend, we had to include him for inspiring Taylor’s gorgeous Speak Now song Enchanted. A staple in Swifties’ worlds, we’re so glad Adam was enchanting enough to give us this banger!

Jake Gyllenhaal

Jake Gyllenhaal is another one of those ex-boyfriends that fans would like to forget, but he sure did inspire some amazing songs after their three-month fling in late 2010! Hey, it may have been a short-lived romance but clearly it left an impact! A shooting star, if you will.

Some of Taylor’s most praised lyricism comes from songs that were inspired by the actor, including We Are Never Ever Getting Back Together, I Almost Do, State Of Grace, All Too Well, Red, The Moment I Knew, Better Man, Babe, and I Bet You Think About Me. Wow!

Years after their love story ended, as Taylor was reworking her catalogue with her own versions amid the war for her Masters, she released a 10-minute version of All Too Well. It was such a masterpiece she had to make a music video for it — and that she did, with herself as the director! Watch the short film starring Stranger Things‘ Sadie Sink and Dylan O’Brien (below):

 

Conor Kennedy

Conor Kennedy was a short-lived love story, but Tay still used him as a muse in one of her earlier songs. They only dated for four months in 2012 and were torn apart after his mother passed away. Begin Again is rumored to be about him, while his grandparents Ethel and Robert F. Kennedy are speculated to have inspired Starlight. 

Harry Styles

Harry Styles had Haylor shippers in a chokehold for so long, despite their relationship only lasting two months in December 2012 and January 2013. Some fans still reminisce on this iconic mid-00s relationship! But who can blame them when he gave us hit after hit, including Out of the Woods, I Know Places, Clean, Style, Is It Over Now?, and Wonderland?! 

Calvin Harris

Calvin Harris was a bleachella moment, that’s for sure. Taylor is rumored to have written Getaway Car, I Don’t Wanna Live Forever, and High Infidelity about her SUPER hot relationship with the producer. They dated from March 2015 to June 2016, making it about 15 months before calling it. 

 

Tom Hiddleston

Tom Hiddleston, just like the previous Calvin, is rumored to have partially inspired Getaway Car. He was rumored to be Tay’s ticket out of her relationship with the Scottish DJ, only staying with him for about four months in mid-2016.

Joe Alwyn

Nine years in a relationship with British heartthrob Joe Alwyn undoubtedly brought us some of Taylor’s most iconic songs. With the most songs on this entire list, the actor boasts being the muse for …Ready For It?, End Game, Delicate, King of my Heart, Dress, Call it What You Want, New Year’s Day, Lover, Cruel Summer, I Think He Knows, Paper Rings, Cornelia Street, London Boy, So Long, London, How Did it End, and the heartbreaking You’re Losing Me. September 2016 has some overlap with her fling with Tom, but these two made it all the way to 2023, near the beginning of The Eras Tour.

Matty Healy

Matty Healy might be Taylor’s most controversial ex of all time, but The 1975 frontman undoubtedly left a lasting mark on this Tortured Poet. She is rumored to have written Fresh Out The Slammer, But Daddy I Love Him, I Can Fix Him (No Really I Can), Down Bad, The Tortured Poets Department, The Smallest Man Who Ever Lived, Fortnight, and Guilty As Sin? about him. A LOT of songs for one month of dating… But their flirtatious history stretches back over a decade!

Travis Kelce

And here we are, with the man of the hour, Travis Kelce! Taylor’s fiancé will definitely have a lifetime of songs ahead of him as he becomes her permanent muse, but as of right now he’s got The Alchemy, So High School, The Fate of Ophelia, Wood, Honey, Opalite, Eldest Daughter, and Wi$h Li$t! Nice! From summer 2023 ’til death.

Were YOU surprised by any of these songs or their inspirations, Perezcious readers? Let us know (below)!

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