I have left Michael Oakeshott till last because his relationship with Iris was perhaps the most improbable of them all. A political philosopher of real stature, who had a short affair and a long friendship with Iris, Oakeshott carried on a vigorous correspondence with her from 1958 to 1963, though their friendship faded in later years. When John Bayley sold her working library in 2003, I wrote a piece about the marginalia. Nine years after their affair in 1950, Oakeshott gave her a book on philosophy “with very much love”, but his guide to the Derby, How to Pick a Winner, was unread. It was Oakeshott who, having broken off the affair, later became the emotionally needy one, as he poured out his woes over an unhappy relationship with a married woman. They were both romantics, although their politics at this stage were at opposite poles: he was becoming the leading conservative thinker of the day, while she was still firmly on the anti-Communist Left. “I suspect you are responsible, by reaction,” she teased him in 1958, “for a lot of my political ideas!” Soothingly, she added: “But my thoughts of you are not political at all.” What seems to have fascinated her about his thought was his critique of rationalism in politics, in favour of custom and experience.
In later years, Iris moved much further in Oakeshott’s direction. She was unimpressed by the radicalism of the 1960s and even more alarmed by the rise of Islamic radicalism after 1979.
Note: “To this period also belongs the book that Oakeshott co-authored with Guy Griffith, A Guide to the Classics (1936), which, to the disappointment of many an earnest student of political philosophy, turned out to be not about Plato and Aristotle but about the fine art of judging horseflesh and picking a Derby winner” (Introduction to A Companion to Michael Oakeshott, p. 3).