First, happiness has nothing to do with his new life, if he doesn't find it inside then his new life is a bandaid on internal unhappiness.

Second, people get funny when it comes to money. With the history between you two, (him feeling you controlled the money and his spending), I wouldn't be surprised that once the vacations are over he starts questioning the "agreement".

Again, there is a chance he just wants to get it over with, but I wouldn't be surprised if this turns ugly since there is money involved.

M(53), W(54),D(19)
M-23, T-25 Bomb Drop - Dec.23, 2017
Ring and Piecing since March 2018