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A passage from Gertrude Stein's Miss Furr & Miss Skeene (1922) is possibly the first traceable published use of the word to refer to a homosexual relationship.
According to Linda Wagner-Martin (Favored Strangers: Gertrude Stein and her Family (1995)) the portrait "featured the sly repetition of the word gay, used with sexual intent for one of the first times in linguistic history," and Edmund Wilson (1951, quoted by James Mellow in Charmed Circle (1974)) agreed.
Pepper's Lonely Hearts Club Band album in the British daily newspaper The Times stated, "The Beatles revive hopes of progress in pop music with their gay new LP".
Ostensibly about schoolboy envy, the song also operated as an in-joke, as related in Jon Savage's "The Kinks: The Official Biography", because the song took its name from a homosexual promoter they'd encountered who'd had romantic designs on songwriter Ray Davies' teenage brother; and the lines "he is so gay and fancy free" attest to the ambiguity of the word's meaning at that time, with the second meaning evident only for those in the know.
Gay is a term that primarily refers to a homosexual person or the trait of being homosexual.
The term was originally used to mean "carefree", "happy", or "bright and showy".
The application to homosexuality was also an extension of the word's sexualized connotation of "carefree and uninhibited", which implied a willingness to disregard conventional or respectable sexual mores. Mac Dermott's music hall song of the 1880s, "Charlie Dilke Upset the Milk" – "Master Dilke upset the milk/When taking it home to Chelsea;/ The papers say that Charlie's gay/Rather a wilful wag!
Such usage, documented as early as the 1920s, was likely present before the 20th century, or in the title of the book and film The Gay Falcon (1941), which concerns a womanizing detective whose first name is "Gay". " – referred to Sir Charles Dilke's alleged heterosexual impropriety.
Far from implying homosexuality, it referred to her free-wheeling lifestyle with plenty of boyfriends (while also punning on Lady Jane Grey).When another character asks about his robe, he responds, "Because I just went gay all of a sudden!