"Kissing a Fool" is a song written and performed by English singer and songwriter George Michael, released by Columbia Records in November 1988 as the seventh and final single from his debut studio album, Faith (1987). It was also the least successful, 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 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.
"Kissing a Fool" was Michael's last single for almost two years in the United Kingdom. It was later covered by Michael Bublé on his self-titled album and released as a single in the United States and reached No. 29 on the Billboard Adult Contemporary chart.
In an interview published in the December 1987 issue of International Musician and Recording World magazine, Michael remembers writing "Kissing a Fool" en route to Japan for Wham!'s 1984 tour (referring to the Big Tour) in early 1985. However, much like other songs Michael was writing at the time, it couldn't be used for Wham! due to certain restrictions in the duo's image; a solo album would be the best chance to use it (which, in that case, turned out to be the Faith album more than two years later).
Michael elaborated on the writing of "Kissing a Fool":
A ballad with minimal instrumentation and a jazz feel, "Kissing a Fool" features arrangement by English film composer John Altman. Aside from Michael's vocals, the song employs piano, guitar, bass, drums and a brass section. According to Michael, the vocals were recorded a cappella in one take.
Personnel taken from Faith liner notes.