Charles Robert Ashbee

Ashbee was born in 1863 in Isleworth, then just west of the Victorian sprawl of London and now a suburb. He was the first child and only son of businessman Henry Spencer Ashbee, the senior partner in the London branch of the firm of Charles Lavy & Co., and Elizabeth Jenny Lavi (1842–1919), daughter of his German business partner. His parents had married in Elizabeth's hometown of Hamburg, Germany on 27 June 1862. His mother's brother Charles Lavy (1842-1928) inherited the German firm and became a politician.

Charles Robert had three sisters Frances Mary (1866–1926), Agnes Jenny (1869–1926) and Elsa (1873–1944) Family life was not happy. As the father became more conservative, his family followed the progressive movement of the era. "The 'excessive education' of his daughters irritated him, his Jewish wife's pro-suffragism infuriated him, and he became estranged from his socialist homosexual son, Charles". Henry Spencer was, like his son after him, well travelled and a writer. He also became a notable erotic bibliophile.

Charles Robert Ashbee went to Wellington College and read History at King's College, Cambridge, from 1883 to 1886, and studied under the architect George Frederick Bodley.

Henry and Elisabeth separated in 1893.

Ashbee has been described as "half-Jewish, Anglican, bisexual, married, Socialist, conservationist, romantic, rebel, fop, and self-described 'practical idealist'".

Ashbee was homosexual at a time when sex between men was a criminal offence. He is thought to have been a member of the Order of Chaeronea, a secret society founded in 1897 by the poet and penal reformer George Ives for the cultivation of a homosexual ethos. He certainly belonged to groups that provided support and understanding to homosexuals.

In 1898, seemingly to cover his homosexuality, Ashbee married the daughter of a wealthy London stockbroker, Janet Elizabeth Forbes (1877–1961), to whom he admitted his sexual orientation soon after she accepted his proposal. During thirteen years of rocky marriage, which included a serious affair of his wife's, they had four children: Mary, Helen, Prudence, and Felicity. Mary Ashbee, later Ames-Lewis (1911–2004) was born at Chipping Campden; Jane Felicity Ashbee (1913–2008), Helen Christabel Ashbee, later Cristofanetti (1915–1998) and Prudence Margaret Ashbee (1917–1979) were all born at Broad Campden.

Ashbee was influenced in his life by the theories of homosexuality developed by Edward Carpenter.