I'm sure if the closeness is there he should know you well enough to understand where you're coming from. I'd just try to ignore the money thing and carry on as usual. (or as close as possible under the circumstances) If he needs an ear to vent into or discuss things you'll be there.

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As to marriage or celibacy, let a man take which course he will. He will be sure to repent - Socrates

Love is not looking in each other's eyes, but looking together in the same direction - Antoine De Saint-Exupery