H. R. P. Dickson was one of six children of John Dickson, a diplomat in the Levant from 1872–1906, and Edith Wills. He was born in Beirut, Lebanon and was taken at a young age to Damascus, Syria where his father was Consul. There his mother's milk failed and Shaikh Mijwal al Mazrab, the husband of Lady Jane Digby, provided the young child with a wet nurse from the 'Anizah tribe. Islamic law lays out the permanent family-like relationships that are created by wet nursing, and this "blood affinity" between Dickson and the 'Anizah meant he was treated as a member of the tribe. He stated that this blood tie 'in later life has been of assistance to me in my dealings with the Badawin of the high desert and around Kuwait'. Following the death of Lady Jane Digby, the Dickson family rented her house in Damascus, and Dickson recalled that he 'spent my childhood days rambling about the lovely garden that had once been [her pride and happiness.'.