Never on the Day You Leave

John Mayer has never been married but he has been romantically involved with several high-profile celebrities including Jennifer Love Hewitt, Jessica Simpson, Taylor Swift, Jennifer Aniston and Katy Perry. This song finds him singing about the heartbreak he went through with after breaking up with one of his former lovers. Mayer said: "That is just the saddest song I ever wrote. It’s about guys and how guys work in regret and it’s never on the day you leave and you can figure out the rest from the title."

In an interview with SiriusXm's Buzz Brainard on August 15, 2017, Mayer spoke about the difficult time he was going through while writing the song. "Not long ago, I ran into my ex," he said without naming any names. "It was very amicable. And I had this beautiful moment where I said, 'A lot of it's me.' A lot of it is in my head, you know. Like, something happened to me and it's just the way I work. It's the way my mind is and I took it really hard. And that took a long time to be able to admit." Mayer added that the song only took him 20 minutes to write, as he poured his emotions into the music.

Mayer said that there is a lyric in the song that is so painful to him, he is unable to perform it live. She'll fight for you like hell, then force herself to like some other man "There's a line in there that is so brutal because it's so true and I can't play the song live because I don't think I'd make it through it," He told Buzz Brainard explaining that in his experience women are totally committed to any relationship they are in but once that loyalty isn't returned they'll find someone else to make them happy. "Every time I sang that line, I would cry in the middle of that line," he added. "It took me days and days and days to be able to sing that line for the record, and get through it without crying."