Hey, I like goal number 4 :-) I also need to start goal #1.
I wonder if your H is mentioning D everyday to test his waters. Since he is really so unsure about the whole thing (he is doing the D paperwork because OW pushed. Really, if he can have it his way, he will be cake eating all the way), he is testing your response to see if he is doing this right. But then, he will still interpret your response in anyway he wants to so in a sense, it does not really matter other than that it is annoying to you.
