Hmm. Well, Chesterton was famous for engaging and debating with some of the highest profile atheists and “progressives” of his day. This would be men like George Bernard Shaw, H.G. Wells, Bertrand Russell, and Clarence Darrow. His disagreements with these men were deep and fundamental. Public debates would sell out and pack auditoriums. However, despite the disagreements, Chesterton was never mean-spirited or hostile. He treated his opponents with respect, humor, grace, and charity. He was actually quite humble (despite sounding bombastic at times), and willing to admit when he was wrong. For this reason, it’s difficult to find an interlocutor who disliked him. Some of his fiercest debate partners were close friends. For me, that’s an ideal I aspire to (and fall oh-so-short of), and the thing I most admire about Chesterton. He stood up for truth. He was not afraid to take unpopular positions (such as when he took the side of both the Boers and the Irish against British Imperialism). But he did it all winsomely… and was very, very funny.
Towards the end of his life, he had an exchange of letters with Wells. Wells wrote:
If after all my Atheology turns out wrong and your Theology right I feel I shall always be able to pass into Heaven (if I want to) as a friend of G.K.C.'s. Bless you.
To which Chesterton replied:
If I turn out to be right, you will triumph, not by being a friend of mine, but by being a friend of Man, by having done a thousand things for men like me in every way from imagination to criticism. The thought of the vast variety of that work, and how it ranges from towering visions to tiny pricks of humour, overwhelmed me suddenly in retrospect: and I felt we had none of us ever said enough. Also your words, apart from their generosity, please me as the first words I have heard for a long time of the old Agnosticism of my boyhood when my brother Cecil and my friend Bentley almost worshipped old Huxley like a god. I think I have nothing to complain of except the fact that the other side often forget that we began as free-thinkers as much as they did: and there was no earthly power but thinking to drive us on the way we went.
That exchange comes from the biography of Chesterton by family friend Maisie Ward, in a chapter called “The Soft Answer”. Truly, GKC was the master of the soft answer. We could use more of his sort in our world today.
Aside from his public exchanges, Chesterton’s kindness came out in other ways. Based on what I’ve read, he and his wife Frances were always opening their home to others. They could not have children themselves, but were always popular with the children around them. Chesterton was extremely famous in his day. I read somewhere that his conversion to Catholicism made front page news even in the US. But he seemed to never let it go to his head (there was no room for it in there anyway), and always had time for ordinary people.