"Kissing a Fool" is a song written and performed by English singer and songwriter George Michael, released on 21 November 1988 by Columbia Records and Epic Records as the seventh and final single from his debut studio album, Faith (1987). It was the least successful single from the album, reaching number 18 on the UK singles chart and becoming the first single in five not to reach number one on the Billboard Hot 100 in the US. However, it reached number one on the Hot Adult Contemporary Tracks chart and became a number 5 hit on the Billboard Hot 100, being regarded critically as one of his most vulnerable recordings and one of his best ballads. In 2021, BBC Radio 2 listeners voted "Kissing a Fool" as number 15 in their top 40 George Michael songs.