"The Second Time Around" is a 1979 hit by Los Angeles–based group Shalamar. The song is the first single from their album, Big Fun. Released in December 1979, the single went to number one on the soul chart and was their most successful hit on the Hot 100 pop chart, reaching number eight in early 1980. "The Second Time Around" also went to number one on the disco/dance chart in January 1980. The song was produced by Leon Sylvers III, who cowrote the song with William Shelby. In 1980, the band made a promotion of "The Second Time Around" for the radio station KJR in Seattle, called "The Sonics Came to Play," dedicated to the Seattle SuperSonics who had won the NBA Championship the previous year.

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Missy Elliott interpolated it in her song "Is This Our Last Time?" from her This Is Not a Test! album.

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