In mid-1891 poet Lionel Johnson introduced Oscar Wilde to Alfred Douglas, an undergraduate at Oxford at the time. Known to his family and friends as "Bosie", he was a handsome and spoilt young man. An intimate friendship sprang up between Wilde and Douglas, but it was not initially sexual, nor did the sexual activity progress far when it eventually took place. According to Douglas, speaking in his old age, "sodomy never took place between us, nor was it attempted or dreamed of. Wilde treated me as an older one does a younger one at school". After Wilde realised that Douglas only consented in order to please him, Wilde permanently ceased his physical attentions.

On the 18 February 1895 Lord Alfred's father, the marquess of Queensberry, left his calling card at Wilde's club, inscribed: "For Oscar Wilde, posing somdomite" [sic!].
Wilde was arrested for "gross indecency" and then imprisoned on remand at Holloway, where he received daily visits from Douglas.
His prosecution opened on the 26 April 1895. Wilde pleaded not guilty. He had already begged Douglas to leave London for Paris, but Douglas complained bitterly; however he was pressed to go and soon fled to the Hotel du Monde.
Under examination Wilde was at first hesitant, then spoke eloquently:
Charles Gill (prosecuting): What is "the love that dare not speak its name?"
Wilde: "The love that dare not speak its name" in this century is such a great affection of an elder for a younger man as there was between David and Jonathan, such as Plato made the very basis of his philosophy, and such as you find in the sonnets of Michelangelo and Shakespeare. It is that deep spiritual affection that is as pure as it is perfect. It dictates and pervades great works of art, like those of Shakespeare and Michelangelo, and those two letters of mine, such as they are. It is in this century misunderstood, so much misunderstood that it may be described as "the love that dare not speak its name," and on that account of it I am placed where I am now. It is beautiful, it is fine, it is the noblest form of affection. There is nothing unnatural about it.

Alfred "Bosie" Douglas

It is intellectual, and it repeatedly exists between an older and a younger man, when the older man has intellect, and the younger man has all the joy, hope and glamour of life before him. That it should be so, the world does not understand. The world mocks at it, and sometimes puts one in the pillory for it."
On 25 May 1895 Wilde was convicted of "gross indecency" and sentenced to two years' hard labour.
He was imprisoned first in Pentonville and then Wandsworth prisons in London. The regime at the time was tough; in November he was so weak from illness and hunger that he collapsed, bursting his right ear drum, an injury that would later contribute to his death. He spent two months in the infirmary. He was then transferred to HM's Prison, Reading, 30 miles west of London.
He was not, at first, even allowed paper and pen, but finally had access to books and writing materials. Wilde requested, among others, the Bible in French, Italian and German grammars, some Ancient Greek texts, Dante's poetry, En Route, Joris-Karl Huysmans's new French novel about Christian redemption and essays by St. Augustine.
Between January and March 1897 Wilde, disgusted by Douglas' insensibility, wrote the so called De profundis.