"If I Was Your Girlfriend" was the second single from American musician Prince's 1987 double album Sign o' the Times. The song was a hit in the United Kingdom but was only a minor hit in America. It was originally from the Camille project of 1986, which was to be released under the guise of Prince's alter ego named Camille. The song is delivered from an androgynous male perspective to a woman, wherein Prince explores the possibilities of a more intimate relationship if he were his lover's platonic girlfriend. Trouser Press names the song as one of the album's highlights, noting that it "redefines a relationship in a surprisingly mature way." It is believed that "If I Was Your Girlfriend" deals with the jealousy Prince felt at the close bond shared between then girlfriend/fiancée Susannah Melvoin with her sister Wendy.

Musically, the song features Prince's pitched-up, androgynous vocals over a sparse bass and drum machine pattern, punctuated by a keyboard line. The opening seconds include a sound collage that includes an orchestra tuning up, a salesman and a sample of Felix Mendelssohn's "Wedding March". According to engineer Susan Rogers, a rare technical error on her part led to distortion—albeit only on certain words. As recounted in Alex Hahn's book Possessed: The Rise and Fall of Prince, Rogers thought Prince "was going to rip my head off" for the mistake. Yet, after hearing the playback, Prince loved the effect, which is featured on the released version.

The song was released on May 6, 1987, and reached number 67 on the US Billboard Hot 100. It was more successful in the UK, reaching number 20 on the chart in that country.

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