Ranking Taylor Swift’s Ex-Boyfriends Based On Songs Written About Them

9. Calvin Harris: Coming in last place is none other than the “boyfriend who’s older than us, he’s in the club doing I don’t know what.” Harris is Swift’s second longest relationship yet if you scan her discography for songs about him, all you get are crickets. He is alluded to in the storylines of “Gorgeous,” “King of My Heart,” and of course, “Getaway Car” but because he is not the main subject of those, I have no choice but to rank him last. Only Taylor Swift could have multiple albums about her many three-month relationships, but only two songs about her relationship of a year and a half. I am interested to see if the reputation (Taylor’s Version) vault will have more songs about their relationship, but at the very least, hopefully we can get This Is What You Came For (Taylor’s Version).

Songs about him: I Forgot That You Existed and High Infidelity

8. Taylor Lautner: As far as I know, “Back To December” is the only song that is confirmed to be about him, but I also think that “Midnight Rain” screams Taylor Lautner because she emphasizes wanting her own name (and if they got married, they would have had the exact same name) as well as the, “I broke his own heart ’cause he was nice” line. Nowadays, Taylor Lautner makes a career out of being the “one good ex” of Taylor’s. And it is honestly kind of annoying. What I will applaud Taylor Swift on is the fact that this was the first song where she admitted to being the problem as opposed to her normal “pointing fingers, I can do no wrong” mindset in her songs from her first three albums. And the strings in “Back To December” are stunning. Her performance of this song on the piano in Central Park lives in my head rent-free. However, due to the lack of content about him, I cannot rank him much higher.

Songs about him: Back To December and Midnight Rain

7. Tom Hiddleston: Nothing good starts in a getaway car. But it does not mean we can’t have some fun in it! Whether it was their PDA-filled Rome vacation or the “I Heart T Swift” shirt, this rebound of hers was insane. It also inspired the iconic “Getaway Car” trumping the sleepier tracks about Lautner and Harris. He is also rumored to be the muse of “Midnight Rain” and if that song is about him over Lautner? Tea.

Songs about him: I Did Something Bad and Getaway Car

6. Conor Kennedy: Conor Kennedy is a forgotten ex, but the songs she writes about him are some of my favorite ones to listen to when I feel hopeful about love. I rank him lower because everybody above him has more range and depth in terms of her songs, but he was a good muse. Without him, Red the album would be even more depressing than it already is. “All I know is we said hello so dust off your highest hopes,” is probably my all-time favorite Taylor Swift lyric so thank you to Conor for inspiring that. Everyone already knows how I feel about, “Begin Again,” so the only song that really brings down his average is “Starlight,” but it’s a cute song about his grandparents. I do not have much else to say about him other than thank you for some of Swift’s most hopeful songs in her entire discography.

Songs about him: Everything Has Changed, Starlight and Begin Again

5. John Mayer: If I had to make this ranking during the Red era, I would have probably ranked John Mayer as number one. For five whole years, “The Story of Us” was my all-time favorite Taylor Swift song. Ours is a classic off of Speak Now and “Treacherous” has been my favorite song off of Red since it came out. “All we are is skin and bone, trained to get along. Forever going with the flow, but you’re friction” makes me sick to my stomach at how good the lyricism is. The reason I ranked him a little lower, however, is because I am not a fan of the song “Dear John.” I know it is a good song lyrically, but it is nearly seven minutes long and is very dark. I mean, what good can come from a 32-year-old dating a 19-year-old? Anyways. I also think that “Superman” is not Swift’s best work. I like the song personally, but on an album like Speak Now, it is one of her worst songs off of the album.

Songs about him: Dear John, The Story of Us, Ours, Superman, Treacherous and I Knew You Were Trouble

4. Jake Gyllenhaal: Oh yes. The man who inspired “All Too Well.” Red is one of my favorite Taylor Swift albums of all time and it was her heartbreak because of him that inspired most of it. When she gives the speech before “All Too Well” on the Eras Tour, she talks about how Red changed the trajectory of her career. It was her first time writing about heartbreak as an adult and there is often the argument to be made that she was never the same after this album. I know that folklore and evermore get all of the attention for being her best lyricism, but Red has some of my favorite lyrics of her entire career. “We learn to live with the pain. Mosaic broken hearts” is one of the best lines she has ever written. Gyllenhaal also gets extra points for inspiring the negative parts of “Begin Again.” We do not stan him, but Taylor Swift writing about her first adult heartbreak led to some of her best lyrics.

Songs about him: State of Grace, Red, All Too Well, I Almost Do, We Are Never Ever Getting Back Together and The Moment I Knew

3. Joe Jonas: If she had dated Joe Jonas for six years instead of Joe Alwyn, he would easily be number two. Though their relationship was short-lived, some of Taylor Swift’s classic songs that never get old no matter how long it has been, were written about him. Outside of Joe Alwyn, he is the only other ex whom she has written about on more than two albums. I don’t think I will ever get tired of “Forever & Always.” I have been obsessed with that song since the first time I heard it and it is the one song that Taylor Swift has specifically admitted on live television who inspired it. “If This Was A Movie” is the most slept-on track in Swift’s discography and it is a stunning song about yearning for the past. One of the reasons Jonas ranks so high is because of the range of songs about him. You’ve got cutesy, “I’m falling in love” songs like “Jump Then Fall” and “Today Was A Fairytale,” the heartbroken ones like “Forever & Always,” “If This Was A Movie” and “Last Kiss” and the ones that look back at their time together fondly like, “Holy Ground” and a few lines in “invisible string.”

Songs about him: Forever & Always, Jump Then Fall, The Other Side Of The Door, If This Was A Movie, Haunted, Last Kiss, Holy Ground and Mr. Perfectly Fine

2. Joe Alwyn: It almost seemed too obvious to put Joe Alwyn at the top of this list (put my name at the top of your list iykyk), but I ranked him below Harry Styles because I think some of Swift’s weakest albums were primarily inspired by him. reputation, Lover and Midnights are constantly at the bottom of people’s album rankings and he was the main muse for all three of those albums. However, Joe Alwyn inspired some of my favorite Taylor Swift songs as well: “Delicate,” “King Of My Heart,” “Cruel Summer,” “I Think He Knows,” “Cornelia Street,” “peace,” “Paris” and my all-time favorite Taylor Swift song of all time: “Hits Different.” I played that song over a thousand times in 2023. There was no way he was not going to be ranked high. Joe Alwyn is too inconsistent for me to make him the number one muse (high highs and low lows) whereas the number one boy is the sonically cohesive muse.

Songs about him: …Ready For It?, Delicate, Gorgeous, King Of My Heart, Dress, Call It What You Want, New Year’s Day, Cruel Summer, Lover, Paper Rings, I Think He Knows, Cornelia Street, London Boy, False God, invisible string, peace, willow, Lavender Haze, Paris and Hits Different

1. Harry Styles: Coming in at number one is Harry Edward Styles. He truly has that “James Dean Daydream, look in [his] eye.” Oh my. 1989 is often regarded as the best album of Taylor Swift’s career (because it is) and he was the muse that catapulted Swift’s career into super stardom. Before 1989 (Taylor’s Version) was released, I thought that Swift had given up on writing deep, meaningful lyrics, but when the vault tracks came out, I realized that she had been so hurt by what happened between her and Styles that she chose to leave off the tracks that detailed the depth of her pain. So far, the 1989 vault is the most iconic and I am honestly not surprised. “You’re not saying you’re in love with me, but you’re going to” and “In a world of boys, he’s a gentleman.” Swoon. Harry Styles, the man that you are. Sometimes there’s nothing left to do but fast forward to 300 takeout coffees later. And the gag on I Know Places (Taylor’s Version) is unreal. He is a difficult ex to dethrone.

Songs about him: Style, Out Of The Woods, All You Had To Do Was Stay, I Wish You Would, How You Get The Girl, I Know Places, Clean, “Slut!”, Say Don’t Go, Now That We Don’t Talk, Suburban Legends and Is It Over Now?