if the x was a jerk and knows nothing about miles, and you set him or her up with all of them anyway and he or she really screwed up your life and you hate her and you feel she or he owes you and you have a chance to do this, I still say do it!
If it is a friend who has no time or inclination to work on a soon to expire account and you have been pushing him to do it but he still wont, and then you go in and use all the miles that are about to expire tomorrow and then send him a check for say, $500, then can he be mad at you?
Gee, I hope not!
There are morals, ethics and rules, but man, there's also discretion and human reality!
Take the miles.