"Darling It Hurts" was the second single by Australian rock group Paul Kelly and the Coloured Girls released in September 1986 from their debut double album, Gossip. The song, written by Kelly with lead guitarist, Steve Connolly, reached No. 25 on the Australian Kent Music Report Singles Chart in October. It was issued in the United States on A&M Records in 1987, where it reached No. 19 on the Billboard Mainstream Rock Chart. Due to possible racist connotations the band changed its name, for international releases, to Paul Kelly and the Messengers. According to Allmusic's Mike Gagne "Kelly's pain can be felt as he describes an ex-girlfriend of his who has turned to prostitution".