How Many of Taylor Swift’s Surprising Exes Have You Forgotten?

by Bethany Lozier

How Many of Taylor Swift’s Surprising Exes Have You Forgotten?

Time to wipe those teardrops off of your guitar, because Taylor Swift is single again. Have you forgotten any of these former flames? Take a trip down memory lane with us.


Drew Dunlap



While his name may not be familiar to you, the song allegedly about him probably is! Swift’s first hit “Tim McGraw” is about her relationship with Dunlap. Though the two broke up after he left for college, Dunlap is a fan of the song and they remain friends.


Jordan Alford



Despite never establishing a formal relationship with him, Swift’s song “Picture to Burn” was inspired by her frustrating relationship with former classmate Jordan Alford. In the song, Swift refers to him as “redneck” who won’t let her drive his truck. Swift later lamented how she handled her teenage angst; but hey–it’s still one of our favorite songs.


Drew Hardwick



The hit that made Swift a household name is partially thanks to former classmate and unrequited love, Drew Hardwick. Hardwick only found about Swift’s romantic feelings towards him when the song “Teardrops on my Guitar” broke the charts — long after Swift healed her own broken heart.


Sam Armstrong



One of Swift’s most popular (and powerful) songs came to fruition after Swift discovered her beau at the time, Sam Armstrong, cheated on her. Swift wrote “Should’ve Said No” as a last minute addition to her titular debut album; the song details her heated confrontation with Armstrong.


Joe Jonas



Ah, the infamous 27-second phone call breakup, who could forget? Though this four-month relationship allegedly inspired a number of Swift’s songs, the former couple seems to be on good terms now, even after Jonas dated one of Swift’s loyal squad members, Gigi Hadid.


Taylor Lautner



Upon meeting on the Valentine’s Day set, these two were smitten. Their five-month relationship ended in late 2009 when Swift penned the heartfelt and apologetic ballad “Back to December”.


John Mayer



John Mayer and T Swift’s three-month relationship in 2010 may have been brief, but it spawned the spectacular song “Dear John”. Swift later confirmed Mayer’s link to the tune, which did not please the male crooner.


Jake Gyllenhaal



The famously talented and good-looking actor also had a notable fling with the singer. However, the two hit a rough patch and split after a few months. Swift’s famous single “We Are Never Ever Getting Back Together” nods at their former couple status.


Conor Kennedy



Yes he’s from THAT branch of the Kennedy clan. Swift’s summer 2012 romance with the politically-connected Conor was cut short, partly due to her busy schedule promoting her album, Red.


Harry Styles



Swift’s time with Styles garnered impressive media interest, even more so after the two split in 2013. The singer herself admitted the breakup was messy, and many assume the songs “Style” and “Out of the Woods” reference the ill-fated relationship.


Calvin Harris



Last but certainly not least, Calvin Harris is the latest to join swift’s squad of storied exes. Harris and Swift dated from March 2015 to June 2016, with Harris confirming the split via Twitter. He still has mad respect and love for Swift, though sources say he was ultimately intimidated by her success.