He was a serious person, and not what Alec Waugh called 'the average boy'. He was not 'in the highest degree conventional', and he was suffering for it. For him there had to be a reason for everything; it had to make sense – and to make one sense, not two. But Sherborne was no help to him in this respect, except in making him more conscious of himself. To be independent he had to work his way through official and unofficial rules alike, and there were certainly no 'ready-made sentiments' for him. At Sherborne the two natural wonders of his life were 'Stinks' and 'Filth'.

If Nowell Smith sometimes had reservations about the public school system, no such doubts assailed Alan's form-master in the autumn of 1927, a certain A.H. Trelawny Ross. A man schooled at Sherborne, who had returned there immediately from Oxford in 1911, he learnt nothing and forgot nothing in his thirty years as a housemaster.18 A stern foe of 'slackness', he shared none of the headmaster's qualms about slavishness. His style of English also contrasted with that of Nowell Smith, his 1928 'house letter' commencing thus: I have a bone to pick with my Captain of the Dayroom (height 4' 11”). He has been telling people I am a woman-hater. This fib was started some years ago by a dame who did not find me gushing enough. My view actually is that a woman-hater has a mental kink, just as a female man-hater has, of whom there are plenty about. …

A narrow nationalist, who had not properly learnt the lesson of loyalty to school as well as to house, Ross was little interested in his form. However, he gave them the benefit of his knowledge and experience of life. He taught Latin translation for a week, Latin prose for a week, and English for a week, this consisting of spelling, 'how to start, write, and address a letter, ' 'how to make a précis, ' 'how a sonnet is built up, and by a typed summary of the main points, to show how to get good sensible, well-arranged written essays.'