Taylor Swift’s Ex-Boyfriends and the Music They Inspired

Taylor Swift is one of the most iconic pop stars of our time - not just for her chart-topping hits, but also for her much-talked-about relationships. From teenage romances to high-profile celebrity flings, each of Taylor Swift’s ex-boyfriends has left a mark not only on her personal life but often in her music as well. If you’ve ever wondered who Taylor Swift dated or are curious about the inspirations behind her emotional lyrics, this list is for you.

In this article, we’ll explore the full timeline of Taylor Swift's boyfriends, spotlighting their relationship moments, rumored breakups, and the songs they inspired.

Joe Jonas (2008)

One of Taylor Swift’s first famous boyfriends, Joe Jonas of the Jonas Brothers, dated her in 2008. Their brief relationship ended when Joe reportedly broke up with her over a 27-second phone call - a detail Swift famously revealed during an interview.

Song Inspiration:

• “Forever & Always”

• “Last Kiss” (allegedly)

Taylor Lautner (2009)

Yes, Taylor dated another Taylor. Swift and Taylor Lautner, star of Twilight, met while filming Valentine’s Day and had a short-lived romance. The two have remained friendly over the years.

Song Inspiration:

• “Back to December” (a rare apology from Taylor in song)

John Mayer (2009–2010)

John Mayer and Taylor Swift's relationship was controversial due to their age difference and rumored emotional fallout. Their brief romance left a lasting impression, especially in Taylor’s songwriting.

Song Inspiration:

• “Dear John” (a scathing ballad about heartbreak)

Jake Gyllenhaal (2010)

Swift’s relationship with Jake Gyllenhaal is one of her most analyzed by fans. Though it lasted only a few months, it led to an emotional period in her life that heavily influenced her Red album.

Song Inspiration:

• “All Too Well”

• “We Are Never Ever Getting Back Together”

• “The Moment I Knew”

Conor Kennedy (2012)

In the summer of 2012, Taylor dated Conor Kennedy, grandson of Robert F. Kennedy. The relationship was short and sweet, with much media coverage due to her frequent visits to the Kennedy compound in Hyannis Port.

Song Inspiration:

• Though no direct songs were confirmed, Begin Again is thought to be loosely inspired by this relationship.

Harry Styles (2012–2013)

One of the most famous of Taylor Swift’s ex-boyfriends, Harry Styles and Taylor's whirlwind romance generated major fan frenzy. From New York strolls to a now-iconic snowmobile accident, the two pop stars had a media-fueled love affair.

Song Inspiration:

• “Style”

• “Out of the Woods”

• “I Knew You Were Trouble” (rumored)

Calvin Harris (2015–2016)

Taylor's longest relationship before Joe Alwyn was with Calvin Harris, a famous DJ and music producer. They dated for over a year and even collaborated on music under a pseudonym.

Song Inspiration:

• “This Is What You Came For” (written under the pseudonym Nils Sjöberg)

• “I Forgot That You Existed” (rumored reference)

Tom Hiddleston (2016)

Swift’s whirlwind romance with Tom Hiddleston began soon after her split from Harris. It was fast, passionate, and widely publicized—remember the “I ❤️ T.S.” tank top?

Song Inspiration:

• “Getaway Car”

Joe Alwyn (2016–2023)

Joe Alwyn and Taylor Swift kept their relationship under wraps for years. Their low-key romance spanned over six years, and many believed he could be “the one.” Unfortunately, the couple reportedly split in 2023.

Song Inspiration:

• “Lover”

• “Invisible String”

• “Peace”

• “Cornelia Street”

• “The Archer”

Matty Healy (2023)

Taylor briefly dated Matty Healy of The 1975 shortly after her breakup with Alwyn. Their fling was intense but short-lived, and sparked plenty of media attention and fan reactions.

Song Inspiration:

• While no direct songs have been confirmed, some fans speculate her Midnights (3am Edition) tracks hint at this era.

Travis Kelce (2023–Present)

Though not an “ex,” Travis Kelce is Taylor Swift’s current partner as of 2025. Their relationship became official in late 2023, and fans are eagerly watching every moment of this high-profile union between a pop icon and an NFL star.

Taylor Swift’s ex-boyfriends have undoubtedly influenced some of the most heartfelt and honest songs in pop history. Whether it’s a passionate love story or a heartbreaking goodbye, each relationship has played a role in shaping her narrative.

While it’s easy to focus on the drama, it’s also a testament to Taylor’s growth - as a woman, as an artist, and as a storyteller. From Joe Jonas to Joe Alwyn, and now possibly Travis Kelce, Taylor Swift continues to write her own story, both in love and music.