Taylor Swift and Her Break-up Songs

Taylor Swift's song "Dear John" - a spiteful message to her past romance with John Mayer

Taylor Swift photo by Eva Rinaldi, John Mayer photo by Steven Eckert, Licensed under CC By 2.0

After a brief 5-month romance with John Mayer (from November 2009 to February 2010) when she was only 19 years old, Taylor wrote “Dear John” in her smash-hit album “Speak Now” referencing to her heartbreak with John Mayer. Mayer felt humiliated by “Dear John”. He thought Taylor Swift hit him below the belt by mentioning about their age gap and how he “painted her a blue sky” then “turn it to rain”.

"You paint me a blue sky

And go back and turn it to rain"

Taylor expressed her regret for trusting John and even loving him blindly:

Well maybe it's me and my blind optimism to blame

Maybe it's you and you're sick need to give love and take it away

And you'll add my name to your long list of traitors who don't understand

And I'll look back and regret how I ignored when they said run as fast as you can

She described John Mayer as a careless heart-breaker with no compassion and remorse for others' feelings:

"All the girls that you've run dry have tired, lifeless eyes

Cause you burned them out"

But then Swift got out of that relationship with her head held high. She was not that young innocent 19-year-old girl who was buried in her heartbreak and couldn't find her way out of the misery:

"But I took your matches before fire could catch me

So don't look now

I'm shining like fireworks over your sad empty town..."