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Taylor Swift's Top 5 Breakup Songs and Who They're About!

Updated: Feb 14

By Zuber

According to Reddit Taylor Swift has written 29/83 heartache songs, equalling 34.93% of her songs. What more is that again thanks to Reddit we discovered that over 9 years Swift has had 15 (known) boyfriends, equalling 1.666.. boyfriends per year, and a break-up every 7.2 months! Wow, poor thing.


5. Out Of The Woods

Having only dated for a few months Harry Styles inspired this classic from Taylor’s 1989 album. Taylor described having constant feelings of anxiety throughout this relationship and conveys that in her song and how much better she felt after ending things.

4. Back To December

Featured in Swift’s Speak Now album (hopefully coming soon as TV), Back to December was written about Taylor Lautner – the only one of her exes who can happily claim to have a song written about them. Swift has admitted that this song is an apology to Lautner “who was incredible to me… and I was really careless with him”. So slay Lautner!

3. Better Than Revenge

Taylor goes all out in this track, taking digs at both her ex-Joe Jonas and his new girlfriend (at the time) Camilla Belle, who got together immediately after Taylor and Joe’s breakup. While Taylor has written a fair few songs aimed at Joe, they are currently friends, with Taylor singing about how “now I send their babies presents” – Invisible String, Folklore.

2. Dear John

Coming a very close second Dear John from Taylor’s Speak Now album calls out John Mayer and what a terrible boyfriend he was. With a 12 (and a bit) year age gap, Taylor and John dated when he was 32 and Taylor was just 19 and asks John in her song “Don't you think I was too young to be messed with?”. Thankfully this relationship didn’t last long, yet the effects of this relationship have still been felt by Taylor years later coming through her song Would’ve, Could’ve, Should’ve from her Midnights (3am edition) album. Lines including “I can't let this go..”, “the wound won’t close…”, and “I regret you all the time…” hint strongly that Taylor has still not healed from this terrible relationship. Plus did you know that John Mayer tried to sue Taylor over this song but lost HAH!

1. All too Well (10-Minute Version)

Not much explanation is needed with this song as the world has already gone through what Jake Gyllenhaal did to Taylor with her re-release of RED (TV). But, like most of RED (TV) Jake Gyllenhaal is once again the muse behind this amazing song (that continues to win award after award). Jake, the narcissistic and awful boyfriend was terrible to poor Taylor, so much so that the world literally turned against him upon the release of All Too Well (10-minute version) and he even turned off his Instagram comments and lowkey hid for months due to the hate he was receiving.

But don’t worry darlings Taylor has bae Joe Alwyn now (6 years and counting)!


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