“The man with the real sense of humor is the man who can put himself in the spectator's place and laugh at his own misfortune.”
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Conservative humor is frankly harder than liberal humor. You get points for just being liberal. You can get more points if you make fun of your own side sometimes.
Honest good humor is the oil and wine of a merry meeting, and there is no jovial companionship equal to that where the jokes are rather small and laughter abundant.
A little perspective, like a little humor, goes a long way.
There is also this benefit in brag, that the speaker is unconsciously expressing his own ideal. Humor him by all means, draw it all out, and hold him to it.
