Ranking Taylor Swift's Songs About Her Ex-Boyfriends

Ranking Travis Kelce’s wife Taylor Swift songs about her exes Jake Gyllenhaal, Joe Jonas, Taylor Lautner, and more (Image via X: Travis Kelce and Taylor Swift)

Why do Swifties love Taylor Swift so much? She speaks from her heart. She writes about what’s happening in her life. She’s authentic to the very core of authenticity. Travis Kelce’s global pop icon wife comes with “a long list of ex-lovers.” And she’s written a song about each one of them. It’s not easy to move on from a broken heart. But when someone turns that heartbreak into a song, it makes you feel like you’re not alone in this heartbroken world. First, her list of long ex-lovers. Then their corresponding songs. And how we’re ranking them!

Travis Kelce’s wife Taylor Swift has a long list of ex lovers from Jake Gyllenhaal, Joe Jonas to Taylor Lautner, Joe Alwyn

Name

Timeline

Key Corresponding Song[s]

Age Difference

Joe Jonas

July – Oct 2008

'Forever & Always', 'Mr. Perfectly Fine'

+4 months [Older]

Lucas Till

Mar – Apr 2009

'You Belong With Me' [co-star fling]

-10 months [Younger]

Taylor Lautner

Oct – Dec 2009

'Back to December'

-2 years, 2 months [Younger]

John Mayer

Dec 2009 – Feb 2010

'Dear John'

-2 years, 2 months [Younger]

Jake Gyllenhaal

Oct – Dec 2010

'All Too Well', 'We Are Never Ever Getting Back Together'

+9 years [Older]

Conor Kennedy

July – Sept 2012

'Begin Again', 'Starlight'

-4 years, 7 months [Younger]

Harry Styles

Nov 2012 – Jan 2013

'Style', 'Out of the Woods'

-4 years, 2 months [Younger]

Calvin Harris

Mar 2015 – May 2016

'I Did Something Bad', 'High Infidelity'

+5 years, 11 months [Older]

Tom Hiddleston

May – Sept 2016

'Getaway Car'

+8 years, 10 months [Older]

Joe Alwyn

May 2017 – April 2023

'Lover', 'Delicate', 'So Long, London'

+1 year, 2 months [Older]

Matty Healy

May – June 2023

'The Smallest Man Who Ever Lived', 'Fortnight'

+8 months [Older]

Ranking Taylor Swift’s songs for past boyfriends based on how strongly each song is related to specific romantic muse [PS some songs are fan theories]:

10. Midnight Rain – Tom Hiddleston

“He wanted a bride; I was making my own name” “He wanted it comfortable; I wanted that pain” “I was sunshine, I was midnight rain” “I broke his heart ‘cause he was nice” “Picture perfect, shiny family” “Holiday peppermint candy” “And he never thinks of me except when I’m on TV.”

9. Our Song – Drew Dunlap

Vulture reports the exact identity of Swift’s first high school boyfriend is unclear, but whether it was Drew Dunlap or Brandon Borello, the story is the same: He was a senior, and Taylor was a freshman. And like many high school couples, they broke up when he went away for college. The songs about Drew Dunlap/Brandon Borello are “Our Song” and “Fifteen” by Tim McGraw. Fifteen lyrics: “Back then I swore I was gonna marry him someday…But I realized some bigger dreams of mine.”

8. But Daddy I Love Him – Matty Healy

“He was chaos, he was revelry” “Sarahs and Hannahs in their Sunday best” “Clutchin’ their pearls sighing, ‘What a mess’” “No, I’m not coming to my senses” “I know it’s crazy, but he’s the one I want.”

7. I Knew You Were Trouble – Harry Styles

Taste of Country’s Megan Pacella reported in March 2013 that Harry Styles was definitely the trouble that walked into Taylor Swift’s life, leaving her head spinning. When she sang “I Knew You Were Trouble” at the 2013 Brit Awards, Swift was able to channel her anger into an impeccable performance, knowing that her ex-lover was standing in the wings watching. “It’s not hard to access that emotion when the person the song is about is standing by the side of the stage watching,” Swift said via the New York Daily News. “You’re balancing the analytical side of your brain, which is telling you where to go and how to go there, with the other side of your brain, which is saying, ‘Feel everything you’re singing and show it on your face. Feel everything exactly as you felt it when you wrote the song.’”

6. Teardrops On My Guitar – Drew Hardwick

“Drew looks at me I fake a smile, so he won’t see That I want and I’m needing Everything that we should be.” According to Taylor Swift Wiki Fandom, the song’s subject is Drew Hardwick. He was her high school crush. The unrequited love she felt for him inspired “Teardrops On My Guitar.”

5. I Can Do It With A Broken Heart – Joe Alwyn

ELLE’s Alyssa Bailey reported Swift addressed fans in the lyrics of the song “I Can Do It With A Broken Heart.” She shared what she was really feeling as she processed the end of her 6-year relationship with British actor Joe Alwyn. “I can show you lies ‘Cause I’m a real tough kid. I can handle my sh*t They said, ‘Babe, you gotta fake it ’til you make it,’ and I did ‘Lights, camera, b*tch, smile Even when you wanna die’ He said he’d love me all his life But that life was too short.” “You know you’re good when you can even do it with a broken heart You know you’re good And I’m good ‘Cause I’m miserable [haha] And nobody even knows Ah, try and come for my job.”

4. I Almost Do – Jake Gyllenhaal

Vulture reported the hidden message of “I Almost Do” is WROTE THIS INSTEAD OF CALLING. “Each time you reach out, there’s no reply.” Smart money’s on Jake Gyllenhaal.

3. High Infidelity – Calvin Harris

“High infidelity Put on your headphones and burn my city Your picket fence is sharp as knives I was dancing around, dancing around it.” “Do you really wanna know where I was April 29th? Do I really have to chart the constellations in his eyes?” StyleCaster’s Lea Veloso reported in Oct. 2022 that Calvin Harris released the song “This Is What You Came For” with Rihanna on April 26, 2016. Taylor Swift was the writer for the song under the pseudonym, Nils Sjoberg.

2. Back To December – Taylor Lautner

Twilight actor Taylor Lautner revealed during a Scream Queens Facebook Live video that Swift’s “Back To December” song was written about their 2009 Taylor-Taylor relationship. The lyrics go as: “I miss your tan skin, your sweet smile So good to me, so right,” and “Because the last time you saw me Is still burned in the back of your mind You gave me roses, and I left them there to die.” Scream Queens co-star Lea Michele joked about Swift writing a song about Lautner. “Didn’t she write a song about you?” “That’s what she does. She writes songs,” Lautner admitted. “It’s something about a hat, right?” Michele pushed. “It’s called ‘Back To December,’” Lautner said.

1. Last Kiss – Joe Jonas

As per POPSUGAR’s Kelsie Gibson, there are six Swift songs seemingly about Joe Jonas: “Forever & Always,” “Better Than Revenge,” “Last Kiss,” “Holy Ground,” “You All Over Me,” and “Mr. Perfectly Fine.” Last Kiss lines: “Never imagined we’d end like this Your name, forever on my lips Just like our last kiss.”