“I Almost Do,” is a song that describes the internal conflict that goes on when reminiscing about a romance. Taylor commented on the song saying—

“I Almost Do'” is a song I wrote about the conflict that you feel when you want to take someone back, and you want to give it another try, but you know you can’t. And you can’t because you know it’s hurt you so deeply that you know that you couldn’t bear to go through that again. So you’re sitting there and wondering where they are and hope that they think about you and that you’re almost picking up the phone call, but you just can’t. I think I needed to write this song in order to not call that person actually. I think that writing the song was what I did instead of picking up the phone.

The same relationship she wrote this song about left her so emotional that she suffered six months of writing block prior to being able to begin writing Red, as she mentioned to USA Today.

There’s a kind of bad that gets so overpowering you can’t even write about it. When you feel pain that is so far past dysfunctional, that leaves you with so many emotions that you can’t filter them down to simple emotions to write about. That’s when you know you really need to get out.

The hidden message written in the album for “I Almost Do” reads, “Wrote this instead of calling.”