[3] "Dear John" was inspired by the end of MacColl's ten year marriage to Steve Lillywhite.

It was originally intended for inclusion on her 1993 album Titanic Days, however she considered it too emotional and personal, and offered it to Reader instead.

MacColl's demo version, which was recorded at Nevin's house, would later surface on the 2005 compilation From Croydon to Cuba: An Anthology.

"[7] In a review of Eddi Reader, Jan Moir of The Guardian described the song as a "big ballad" and considered it the best track on the album.

[8] Rick Anderson of AllMusic felt "Dear John" was "perhaps the tenderest kiss-off song ever written".