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> I’ve seen where people answer it honestly, and when they walk away the person asking says something to the effect of, “god, I didn’t need his whole life story.”

I've definitely experienced the same. However ive realized that invariably, the person answering honestly is wayyy happier in general than the person being critical. Learning to have the freedom to express yourself, invite connection, and let failed invitations go, is a superpower for a happy life.