The first song that Swift wrote for Red, she penned the tune in 2011 with Liz Rose, one of her co-writers on her first three albums. The heart-rending break-up tune came after a six-month writing block that followed a particularly painful ending of a relationship. "There's a kind of bad that gets so overpowering you can't even write about it," she told USA Today of that time. "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."

Swift was asked by The Daily Beast if she ever felt guilty regarding writing about an ex. She replied: "I take these songs and these people who inspire these songs on a case-by-case basis. If there were someone who was a good person, I'm not going to write something bad about them. But if they handle a situation in a way that really messed up my life for a while, that's what I'm going to write about. For me, I've never changed the reason I write a song. Songs for me are like a message in a bottle. You send them out to the world and maybe the person who you feel that way about will hear about it someday."

Taylor is a noted fan of singer/songwriter Matt Nathanson of "Come On Get Higher" and "Run" fame, to the extent that she has been known to perform with the lyrics of his song "Modern Love" written on her arm. Fans have pointed out the similarity between a lyric in this song ("And I forget about you long enough to forget why I needed to"), and a line from Nathanson's 2003 tune "I Saw," ("And I'll forget about you long enough to forget why I need to").

Maybe Taylor wanted to pay homage to Nathanson or it may be simply unconscious plagiarism on her part. However, Nathanson seems to believe it to be plagiarism. According to the Gawker site, he posted a tweet after the rumors first surfaced that was subsequently deleted, in which he wrote, "She's definitely a fan, and now she's a thief."

"All Too Well" is said to be based on Taylor's relationship with actor Jake Gyllenhaal, whom she dated for three months in 2010. During the song, she sings:

Left my scarf there at your sister's house,
And you still got it in your drawer even now

When Jake's sister Maggie Gyllenhaal sat down with Andy Cohen on Watch What Happens Live, she was asked whether Taylor once left a scarf at her house. The actress looked bewildered and replied, "You know, I never understood why everybody asked me about this scarf. What is this? I am in the dark about the scarf."