As horrible as it is to see a man cry, it actually sounds like he is putting some pressure on himself now about this issue. It means he realizes there's something wrong, and feeling it.
I think your approach to this situation was perfect, and your responses to him were spot on. It leaves everything in his hands, so he has to make these choices from now on. I agree, if money ever goes missing again, then that's his way of choosing his own fate.
I'm proud of you, even if that pride is just from some random stranger on the internet
I hope you two can both find your feet together again.
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