"Kissing a Fool" is a song written and performed by English singer and songwriter George Michael, released by Columbia Records in 1988.

A ballad with minimal instrumentation and a jazz feel, the song was written about Michael's insecurities as a soulmate and partner because of the baggage and reputation with which he came.

[citation needed] Aside from Michael's vocals, the song employs piano, guitar, bass, drums and a brass section.

[3][4] In 2021, BBC Radio 2 listeners voted "Kissing a Fool" as number 15 in their top 40 George Michael songs.

According to 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!