Part of the longstanding drama around Taylor has been her relationships. With titles like “serial dater,” it’s no wonder Taylor has kept her now 3-year relationship with Joe Alwyn out of the spotlight – besides her very telling music, of course (cc: entire reputation album and songs released on Lover so far). The thing about Taylor that really separates her from her peers is that she actually writes her own music, so it’s always extremely personal. She’s been criticized and praised for this – the honesty is something to be admired, but it’s also very exposing not only for her, but also the public men she writes about. HOWEVER, we would be remiss to not review a few of her famous beau’s and our favorite songs that they’ve inspired (starting with Joe Jonas because the earlier men aren’t famous (e.g. Drew from Teardrops On My Guitar).

Joe Jonas

LOS ANGELES, CA – SEPTEMBER 07: Singers Taylor Swift and Joe Jonas at the 2008 MTV Video Music Awards at Paramount Pictures Studios on September 7, 2008 in Los Angeles, California. (Photo by Jeff Kravitz/FilmMagic) (via People.com)

Joe inspired the song “Forever & Always.” He broke up with her over a 27 second phone call, which she publicly complained about. She then convinced her record company to let her record a last minute song about him to put on Fearless. We’ll forgive Joe for this because it led to him being with Sophie Turner and we all know Jophie is OFD’s favorite couple. Joe also inspired two songs on Speak Now. “Last Kiss” and “Better Than Revenge” are about Joe’s ex-girlfriend Camila Belle, but “Forever & Always” off Fearless takes the cake for me.

Taylor Lautner

Taylor Squared in the 2010 movie “Valentines Day” (via CBS News)

Taylor and Taylor (referred to at the time as Taylor Squared) met on the set of the film “Valentines Day” (a great bad movie by the way). Rumor has it he was way more into her than she was into him and “Back to December” off Speak Now is suspected to be an apology song written for him. “So this is me swallowing my pride, standing in front of you saying sorry for that night” and “you gave me all your love and all I gave you was goodbye” are evidence in the lyrics to support this theory.

John Mayer

John Mayer and Taylor Swift perform during Z100’s Jingle Ball 2009 at Madison Square Garden in New York City. (Theo Wargo / WireImage / Getty Images) (via LA Times)

“Dear John” and “I Knew You Were Trouble” are rumored to be about John Mayer who she dated briefly after they collaborated together on his song “Half of My Heart.” We all know JMay has a tumultuous dating history as well so it only fits that the two of them dated and both got great songs out of it. I was very pro this relationship and breakup.

Jake Gyllenhaal

Jake Gyllenhaal and Taylor Swift take a stroll through Brooklyn on Thanksgiving Day in 2010. (Photo: Swarbrick/INFphoto.com) (via US Weekly)

Jake was special in that he had 4 full songs written about him on the Red album – the most ever (that we think we know of) until Joe on reputation. He inspired “We Are Never Ever Getting Back Together,” “State of Grace,” “The Moment I Knew” and “All Too Well.” There are a lot of rumors surrounding this relationship and why they broke up: that he was too old for her (he was 29, she was 21), that he was a playboy, that he couldn’t commit, and on and on. Their reported on-again-off-again relationship supposedly took a toll on Taylor and while I don’t know what’s true and what’s not, I do know that “All Too Well” is an extremely emotionally vulnerable song. If it is about him, which all signs point to, then he did inspire lyrics like “Maybe we got lost in translation, maybe I asked for too much / And maybe this thing was a masterpiece ’til you tore it all up / Running scared, I was there, I remember it all too well / Hey, you call me up again just to break me like a promise / So casually cruel in the name of being honest. / I’m a crumpled up piece of paper lying here / ‘Cause I remember it all, all, all too well.” I don’t know about you but that sounds like someone who has been gut punched by a relationship. Jake definitely wins my vote for best inspired song, for whatever that may be worth. 

Conor Kennedy

Taylor and Conor on the Kennedy’s boat in Hyannis Port, MA in 2012 (via Hollywood Life)

Off Red, “Begin Again” is supposedly about Conor Kennedy and “Starlight” is apparently about Conor’s grandparents Ethel and Robert F. Kennedy. This is probably Taylor’s weirdest celeb dating experience yet – Conor was only 18 when they dated and Taylor seemed way too happy to just be around the Kennedys. She really embraced the Hyannis summer vibe, which I guess I can’t blame her for – the Kennedy boat is really nice after all. Side note: This relationship was hilarious because Conor was in my year at a Northeastern boarding school that had dances with my high school. One of my friends kissed Conor when we were freshman in high school at a school dance and she’ll never let us forget that she and Taylor kissed the same guy. 

Harry Styles

 Taylor Swift and Harry Styles are seen walking around Central Park on December 02, 2012 in New York City. (Photo by David Krieger/Bauer-Griffin/GC Images) (via Teen Vogue)

“Out of the Woods” and “Style” on 1989 are reportedly about Harry Styles. When asked about the songs in a Billboard interview, Harry explained, “I’m lucky if everything [we went through] helped create those songs. That’s what hits your heart. That’s the stuff that’s hardest to say, and it’s the stuff I talk least about. That’s the part that’s about the two people. I’m never going to tell anybody everything.” I respect that – I’m also on record saying that I absolutely love the song style, so I’m all in on their relationship/break-up dynamics and apparently so is Harry! 

Calvin Harris (and Tom Hiddleston)

Calvin Harris (real name Adam Wiles) were together for over a year and unfortunately he didn’t get to make it into a sappy love song although they appeared quite in love on social media. A picture appeared on social where the two went on vacation and drew “TS + AW” in the sand.

TS + AW in 2016 (via E! News)

Instead, “I Did Something Bad” and “Getaway Car” were written about him on reputation. Plus, he has to share “Getaway Car” with Tom Hiddleston as the song refers to Taylor’s whirlwind rebound with Tom right after breaking up with Adam. There was also drama when Taylor sang background vocals on Calvin Harris’ song “This Is What You Came For” and for some reason no one was supposed to know. Taylor eventually came out and took credit for helping to write the song (which if it’s true, she deserves that credit) and people came after her for being selfish. This was a messy relationship that I honestly wish produced more songs. But “Getaway Car” is an all-timer. 

Hiddelston wearing an I <3 TS shirt at Taylor’s Rhode Island star-studded 4th of July bash in 2016 (via Mirror)

Winners (and Losers)

After recapping all of that drama, I’d like to address that my favorite songs to come out of those breakups are “All Too Well,” “Getaway Car” and “Forever & Always”… so thank you to Jake Gyllenhaal, Tom Hiddleston / Calvin Harris, and Joe Jonas for your contributions to Taylor Swift’s discography. 

Past, Present, Future: Joe Alwyn

Joe and Taylor at the BAFTAs in 2019. (via E! News)

I hope this article will forever end here. Taylor seems extremely happy with Joey (you say Joe rest of the time, but Joey here – does he go by both?) Alwyn, her bf of almost 3 years now. Joe was the inspiration for the majority of reputation other than the aforementioned songs and the ones she directs at the general public of haters. “Delicate”, “Dress”, “So It Goes…”, “King of My Heart”, “Call It What You Want”, “Gorgeous”, and “New Year’s Day” are all supposedly about Joe. We also only have 4 songs so far from Lover and two, “The Archer” and “Lover” are about Joe. Extremely happy that Taylor is happy and I’m looking forward to listening to the rest of Lover to hear more about this positive relationship..