The Definitive Ranking Of Taylor Swift's Songs About Boyfriends

Whether you like Taylor Swift or not, you definitely know something about her illustrious dating history hell, she’s written some sweet hits using those heartbreaks.

Because the pop star’s dating history includes a roster of high-profile relationships AND her music catalogue just reappeared  on all streaming services, we’ve decided to make the ranking to end all Taylor Swift rankings:

These are the TSwift songs about boyfriends, RANKED:

1) “All Too Well” Jake Gyllenhaal

2) “Back To December”  Taylor Lautner

3) “Should’ve Said No” Sam Armstrong

4) “Style” Harry Styles

5) “Fifteen” Brandon Borello

6) “Forever & Always” Joe Jonas

7) “Dear John” John Mayer

8) “Out of the Woods” Harry Styles

9) “Holy Ground” Joe Jonas

10) “I Knew You Were Trouble” Harry Styles

11) “Better Than Revenge” Joe Jonas

12) “Our Song” Brandon Borello

13) “Tim McGraw” Tim McGraw (just kidding! Brandon Borello)

14) “We Are Never Ever Getting Back Together” Jake Gyllenhaal

15) “Last Kiss” Joe Jonas

16) “The Last Time” Jake Gyllenhaal

17) “Begin Again” Conor Kennedy

18) “Picture To Burn” Jordan Alford

CLEARLY, this list is evidence that: Jake Gyllenhaal was the Yoko Ono to Swift’s John Lennon. 

Honorable mentions include songs about rumored boyfriends/crushes: “Hey Stephen” Stephen Liles, “Teardrops On My Guitar”  Drew Hardwick, “Mine” Corey Monteith, and “Enchanted”  Adam Young.  

You’ll notice Calvin Harris and Tom Hiddleston are not on this list. That’s because those relationships (and subsequent breakups) were recent and Swift has not dropped any music with allusions to either in the interim. But ... we have every confidence that the Harris-as-Taylor’s-muse music will make this list change in one way or another.

Oh, and we put all these songs in a playlist for you to scream-sing with us: 

Keep writing songs about your love life, Tay. We’re here for it.

Muses for this piece: Abigail Williams, Melissa Radzimski, Samantha Tomaszewski, Kate Palmer, Jill Capewell, Travis Waldron, Christopher Mathias, Stephanie Marcus and Leigh Blickley.