This is a track from the self-titled debut album by the Court Yard Hounds. The American Country duo were founded as a side project of the Dixie Chicks by sisters Emily Robison and Martie Maguire.
Emily Robison wrote this song and she explained the inspiration behind it during a web chat. "'Then Again' is an amalgamation of different people I've know through relationships, or just growing up with or have observed in my life," Emily disclosed. "I put them all in one person and went with experiences and stories that I've had in my head for the last few years and made this one person... It's more introspective, how I wish had spoken up."