Taylor Swift’s most famous songs are often seen as diss tracks about her ex-boyfriends. From high school breakups that inspired her early music to recent relationships with Joe Alwyn and Matty Healy, she’s known for turning her heartbreak into hit songs.
Jordan Alford
Taylor’s high school crush who dated her friend, Chelsea, leading to “Picture to Burn.”
Brandon Borello
A high school sweetheart who inspired “Our Song” and “Tim McGraw” after moving away for college.
Sam Armstrong
Cheated on Taylor, inspiring “Should’ve Said No.”
Joe Jonas
Famously broke up with her in a 27-second call, leading to “Forever and Always.”
Lucas Till
A brief romance during “Hannah Montana: The Movie,” but no breakup song ensued.
Taylor Lautner
Their short relationship inspired “Back to December.”
John Mayer
Their controversial romance led to “Dear John.”
Corey Monteith
Inspired “Mine” after a brief time together.
Jake Gyllenhaal
Their age-gap relationship inspired “We Are Never Ever Getting Back Together” and “All Too Well.”
Conor Kennedy
Their summer romance led to “Starlight” and “Begin Again.”
Harry Styles
Their month-long fling inspired “I Knew You Were Trouble” and “Style.”
Calvin Harris
A 15-month relationship that ended with “I Forgot That You Existed.”
Tom Hiddleston
A whirlwind romance that resulted in “Getaway Car.”
Each of these relationships contributed to Taylor’s repertoire of heartfelt and fiery breakup anthems.
