"Darling It Hurts" was the second single by the Australian rock group Paul Kelly and the Coloured Girls released in September 1986 from their first, 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 1987 on A&M Records in the United States, 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."

After recording his solo album, Post in early 1985, Kelly established a full-time band in Sydney. It included Michael Armiger (bass guitar, rhythm guitar), Michael Barclay (drums, ex-Weddings, Parties, Anything) and Steve Connolly (lead guitar). Bass guitarist Jon Schofield and the keyboard player Peter Bull soon joined. Through a joke based on Lou Reed's song "Walk on the Wild Side", the band became known as Paul Kelly and the Coloured Girls. Armiger left and the Coloured Girls line-up stabilised in late 1985 as Barclay, Bull, Connolly and Schofield.

By May 1986, the band entered Trafalgar Studios and released their debut 24-track double LP, Gossip in September. It included remakes of four songs from Post.Gossip peaked at No. 15 on the Australian Kent Music Report Albums Chart. Singles from the album were "Before Too Long" which peaked at No. 15 on the related Singles Chart and "Darling It Hurts" which reached No. 25. The song was written by Kelly with lead guitarist, Steve Connolly.

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