It is very possible that he knows that you do not really mean "it's over" literally. Using that repeatedly could desynthesize him to it – and it will not have the same effect after that.
Reminder appreciated. The thing is, I meant it. I wasn't flipping out or yelling. I just told him that if his life was so damned miserable, and the thought of a cold winter day was making his life hell - IN JULY - then he should go. If he had taken me up on it, then that would have been ok. too. I refuse to go back to a life where every time things aren't perfect, I have to hear about how everything sucks.
LOVE THE STORIES HERE!! Cheese, douches, keys ready to open a door, and calling him a little bitch - ah, ain't love grand?