re: A good buddy called me asking for money yesterday. Update 6/12

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mean, you took the practical approach for both you and him. How he responds to that is on him. It sucks, but so does their situation.

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Meh

I think you can loan, or lend advice but discussing loaning while commenting on his lifestyle is a risky way to handle it.

“Hey I’m going through it too - we are cutting back here, sorry I can’t help. Have any expenses that you could shed too?”

Or

“Here’s some cash” and don’t truly expect it back

Are the only two answers for him. I would give you money if you weren’t such a frick up goes over terribly all the time.