In 1898, whilst appearing at the Cambridge Footlights club, he met and had an affair with the then unknown Aleister Crowley. Crowley describes his lover:
'Pollitt was rather plain than otherwise. His face was made tragic by the terrible hunger of the eyes and the bitter sadness of the mouth. He possessed one physical beauty - his hair. This was very plentiful and he wore it rather long. It was what is called a shock. But its colour was pale gold, like spring sunshine, and its texture was of the finest gossamer.'

Pollitt was also a friend of Aubrey Beardsley, and was painted by James Whistler. He was an art collector. He was the original of the 'Babe' in E.F. Benson's 'The Babe, B.A.'.
Crowley immortalized Pollitt in The Scented Garden of Abdullah the Satirist
Pollitt did not share Crowley's spiritual quest, and Crowley ended the affair shortly after going down from Cambridge in 1898. He later recognized this as an 'imbecile' mistake, and he continued to regret it.
- Aleister Crowley, (ed John Symonds and Kenneth Grant). The Confessions of Aleister Crowley: An Autohagiography
. Bantam Books. 1971: 130-2,137-8.
- Susan Roberts. The Magician Of The Golden Dawn: The Story Of Aleister Crowley.
Contemporary Books, Inc. 1978: 34-5.
- John Symonds. The Great Beast: the Life and Magick of Aleister Crowley
. Mayflower. 1973: 177-8.
- “Pollitt, Herbert Charles Jerome, 1871-1942, collector. Photograph albums: Guide”. Harvard University Library. http://oasis.harvard.edu:10080/oasis/deliver/~hou01559.
- Alex Owen. "Aleister Crowley in the Desert". www.press.uchicago.edu/Misc/Chicago/642011.html.
Crowley (1875 - 1947) says that Pollitt was ten years older, and this has been repeated in many places, but the age difference was actually only four years.
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