I think you're right that "cynic" is a deliberate cover for and distancing from his actual feelings (which are very deep and painful), rather than any philosophical attitude he feels naturally. I'd suggest his so-called cynicism goes hand-in-hand with his continual inability to identify his feelings: this is a man who's been training himself for years upon years to not credit or notice any feeling beyond irritation.

Because it is very clear that this man feels things very deeply: he would not have taken his prior rejections so hard as to reject all friendships, otherwise. And of course there's all the everything with Ewen. The way Keith just loses his shit all over Loudoun... wow.

(And that driving need to get back to Ewen to explain himself! So that Ewen not think poorly of him! Or think himself betrayed!)

I'm uncomfortable with you re all these "womanish" descriptions of Greening. :-/

And yay, thank you for more historical write-up!