The song's lyrics are based on love letters between American author F. Scott Fitzgerald and his wife Zelda. Gibbard's source was a book, Dear Scott, Dear Zelda, which contains all the correspondence between the pair throughout their lives. Gibbard explained to Consequence of Sound: "In that song, that's an important detail in knowing and understanding the song. I don't know who could have tied it all together. Who could have figured out what the song was about given the geographical locations and a very deep knowledge of F. Scott Fitzgerald's work, probably not many. I've been so fond of those letters that they wrote back and forth for a long time. There were so many beautiful stories within them, and I wanted to tie a little piece of them together to do a song."
The song finds Gibbard duetting with singer-songwriter Aimee Mann. He told Rolling Stone: "We've been friends for a while. She killed it, and she's also hilarious. The whole making of this record, we were laughing the whole time."