Benson was an intensely discreet homosexual.[8] At Cambridge, he fell in love with several fellow students, including Vincent Yorke (father of the novelist Henry Yorke), about whom he confided to his diary, "I feel perfectly mad about him just now... Ah, if only he knew, and yet I think he does."[9] In later life, Benson maintained friendships with a wide circle of homosexual men and shared a villa on the Italian island of Capri with John Ellingham Brooks;[10] before the First World War, the island had been popular with wealthy homosexual men.
Homoeroticism and a general homosexual sensibility suffuses his literary works, such as David Blaize (1916), and his most popular works are famed for their wry and dry camp humour and social observations.
Benson was a good athlete, and represented England at figure skating.
In London, Benson also lived at 395 Oxford Street, W1,[Note 2] where much of the action of Lucia in London occurs and where English Heritage placed a Blue Plaque during 1994.