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. According to Michael, the vocals were recorded in a cappella in one take. "Kissing a Fool" was the working-title for the album, which later was renamed to Faith.

Aside from Michael's vocals, the song employs piano, guitar, bass, drums, and a brass section. It was the seventh and final single to be released from the album Faith. It was also the least successful, making number 18 on the UK Singles Chart and becoming the first single in five not to make 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, remaining a fan favourite and being regarded critically as one of his most accessible and honest recordings.

"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 number 29 on the Billboard Adult Contemporary chart.

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