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I agree with this. Find out if there was SO for the dinner because this doesnt make sense. They always allow the SO to the dinners…
That’s funny that you mentioned gambling because he blew $100k on it in one year
That's it. You can emotionally sand down the other rough edges, but this is an undeniable fact.
Has he noticed this was wrong? Has he taken steps to do better and not fall down into that hole again?
Nothing wrong with a little gambling but you need to be self-aware enough to realize it tickles you in the most vulnerable parts of your psyche, so you need to either be able to gamble responsibly (a separate can of worms entirely) or not at all.
100k is not responsible. If he has not, of his own volition, described that spending as wrong you need to get out and find somebody who is better aligned with your views on money management.