Songfacts®:

• The Head and the Heart contributed this song to Cameron Crowe's dramedy, Roadies. The group also ended up playing a role an opening band in the Showtime series.
• Co-frontman Jonathan Russell had already written parts of the song during the recording of The Head and the Heart's Let's Be Still album. Pianist Kenny Hensley explained to Radio.com: "The offer for Roadies came about and it was the kind of song that had been sitting and we hadn't finished so we took it as an opportunity to kind of hunker down in the studio for a couple days, finish something to offer them and see what comes out of it."
• Russell explained the song's meaning to Radio.com: "Everyone's gone through a relationship where things didn't work out… you try it again and it doesn't work out," he said. "That feeling of 'Why are we doing this to ourselves? We know it's not going to work out. We've tried it before. Just let it go.'"
• Russell's initial impetus for penning the song was the realization that he'd chosen the life of a musician over an amazing relationship. "What the hell are you doing?" he recalled asking himself. "That's where my head was at when I started that song."