Taylor Swift’s Boyfriend Timeline: 12 Relationships & Their Songs (2024)

• Taylor Swift’s Boyfriend Timeline: 12 Relationships & Their Songs

  

  As a country pop darling-turned-"Reputation"-slayer, Taylor Swift has certainly become known for writing songs about the ghosts of boyfriends past. So let's play a familiar game: Which song is about which of Taylor's ex's? We plowed through some of Swift's biggest hits and matched the lyrics to 13 of Swift's high-profile (reported) former relationships. It's all based on clues, speculation and a few rumors, so there's no guarantee we got 'em all right. But here are our guesses — look and listen.

• Joe Jonas (July 2008-October 2008)

  

  Before he broke up with her over a 27-second phone call, Joe Jonas and Taylor Swift seemed to be going strong. Her original reactions to the break-up — "Last Kiss" and "Forever and Always" — were a little more scathing, but her latest perspective on the Jonas Brother — "Holy Ground" — is a lot more positive. She seems to have gotten over Jonas and is looking back at all the things she loved about dating her fellow pop star.

• Lucas Till (March 2009-April 2009)

  

  Swift's "You Belong With Me" co-star Lucas Till won her heart on the set of the hit music video, but their relationship was short-lived. There didn't seem to be much drama, which is perhaps why Till seems to never have had a Swift song written about him. He later spoke out about their brief try at dating, saying that it "didn't work out" because he "really just liked her as a friend." Ouch.

• Taylor Lautner (August 2009-December 2009)

  

  On the Speak Now single "Back To December," Swift apologizes (when does she ever do that?) to an ex for a rough night, a night that very well could have been the one when she dumped actor Taylor Lautner. Why assume she's talking about the former teen wolf, who first caught Swift's eye on the set of their "Valentine's Day" flick? Well, she referenced his "tan skin" and "sweet smile." The guy's both of those for sure.

• John Mayer (December 2009-February 2010)

  

  What likely began as a sweet 2010 summer connection ended on a sour note and, of course, in song (or, more likely, several songs). At 19, Swift seemed to think that John should have treated the delicate country flower with a little bit more care. Shrewdly entitling the cut after Mr. Mayer's first name, she spewed out lines like, "Don't you think I was too young to be messed with? The girl in the dress cried the whole way home. I should've known." Geez, that's heavy.

• Cory Monteith (April 2010-May 2010)

  

  Swift explained to Yahoo that the "Speak Now" song "Mine" was about a guy, "that I just barely knew put his arm around me by the water, and I saw the entire relationship flash before my eyes." Neither Swift nor the late "Glee" star Cory Monteith ever confirmed that they were dating — although both turned bright red when Ellen DeGeneres breached the subject — but if not, she has an imagination great enough to dream up a solid song about what could have been.

• Jake Gyllenhaal (October 2010-January 2011)

  

  In an NPR interview, Swift explained that "The Last Time" is about an "experience I had with someone who was kind of this unreliable guy. You never know when he's going to leave, you never know when he's going to come back, but he always does come back." Between acting in flicks that take him all over the world and the bevy of gorgeous options Jake Gyllenhaal likely has, it's not too far of a stretch to think Swift is singing, "Put my name at the top of your list," about him.

• Eddie Redmayne (October 2011-January 2012)

  

  "My Week With Marilyn" star Eddie Redmayne was rumored to be dating Swift for a few months in 2011, but up until recently, the 31-year-old actor is still denying that the relationship ever happened. Whether or not they did have the reported three-month fling, Redmayne doesn't appear to have made enough of an impact to earn a song on the pop princess' latest release.

• Zac Efron (February 2012-March 2012)

  

  Taylor and Zac Efron reportedly started dating for a few months while promoting their movie "The Lorax" in the first part of 2011. Both deny the rumors, however, and it doesn't seem like Efron was attached to any of the songs on "Red." The pair did write a song about their relationship, denying the dating rumors through a parody of Foster the People's "Pumped Up Kicks" on Ellen DeGeneres' talk show.

• Conor Kennedy (July 2012-October 2012)

  

  During an interview with Ryan Seacrest, Taylor explained that her single "Begin Again" is about, "When you've gotten through a really bad relationship and you finally dust yourself off." Coincidentally, the then 22-year-old was enamored with 18-year-old Conor Kennedy. Seems like he was the reason she was singing lyrics like, "I think it's strange that you think I'm funny 'cause he never did."

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  Taylor's rocky, brief relationship with One Direction's Harry Styles was scrutinized by the media from the day the pair stepped out together. Before they were officially a couple — but months after they had a rumored fling in April 2012 — Swift wrote "I Knew You Were Trouble.,” from “Red,” about Styles. Once they broke up, all she had to tweet was a lyric from the song: "…'til you put me down," for fans to know it was over. Two years later, the “1989” highlight “Out Of The Woods” is widely assumed to be about Styles, with lyrical references to their December romance and snowmobile accident.

• Calvin Harris (February 2015-June 2016)

  

  This duo met through a mutual friend, Ellie Goulding, back in February of 2015 at The Brit Awards and immediately hit it off. As one of Swift's longest running relationships, the couple was a match made in music heaven, spending July 4 holidays together on the beach and celebrating their one year with a homemade cake (all documented on Instagram.) Of course, all good things come to an end, and when it got ugly, it got really ugly (via Twitter). In Swift's single music video for "Look What You Made Me Do", she lends an eery nod to Harris by crawling out of a graveyard next to a headstone reading "Nils Sjoberg," which was the psydenomthe singer used to conceal her identity on Harris and Rihanna'sh*t track, "This is What You Came For".

• Tom Hiddleston (June 2016-September 2016)

  

  Well, that was a hot flash in the pan! Mere days before her very public breakup with dance EDM artist Calvin Harris, Swift was seen dancing with actor Tom Hiddleston at The Met Gala in May of 2016. Then, a few days post-Harris breakup, Swift and Hiddleston are seen sitting on the beach kissing and cuddling. After three months of allegedly intense romance, "meeting the parents" and spending a different fourth of July with Swift's "Squad", the couple broke it off in early September. Also in the music video for "Look What You Made Me Do," Taylor has a group of male dancers wearing shirts with "I <3 TS" written on the front; a direct reference to the famous white tank Hiddleston wore (and got massively trolled for) during their public July 4 weekend.

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