Saddest Taylor Swift Songs?

[Sneaky 7,655]

Exile is pretty tough

[Reject False Icons 2,821]

Seven  remembers me of my childhood best friend who moved unexpectedly and I haven’t had any contact since 

i wish her well and I wish she remembers me 

 

Edited September 22 by Reject False Icons

[PrinceOfTheStorm 5,831]

this is me trying is literally my mental health in a song. I didnt even realize it until I relistened to the album recently.

God too many lines in that hurt like a truth.

[alicefromabove 5,912]

Bad blood because she bullied Katy

[funkyhaus 6,925]

I find Seven quite sad 

“And I've been meaning to tell you
I think your house is haunted
Your dad is always mad and that must be why
And I think you should come live with
Me and we can be pirates
Then you won't have to cry
Or hide in the closet
And just like a folk song
Our love will be passed on”

[StrawberryBlond 10,481]

Not the biggest fan by any means but these ones get me:

Tim McGraw - I won't pretend I haven't amended parts of the chorus to suit a situation of mine.

Teardrops On My Guitar - Classic song for any teenage girl who ever had an un-reciprocated crush.

Dear John - If it is true that John Mayer is who she lost her virginity to, this might be her saddest song ever.

Begin Again - Even if you think Taylor dates too much, the way she sings "break and burn and end" run deep.

Safe & Sound - Sounds almost like a lullaby for someone who's about to die, a beautiful melancholy vibe to it.

Illicit Affairs - Not actually my favourite song on the album but the subject matter is just brutally executed.