ooooohhhhh (((Sept)))

I hate to say this, but I can see why you haven't had a response from your son. You did a great job of trying to be tactful but straightfoward, and there is a LOT of good advice in there. But, there are two things that are rubbing me wrong:

1) Word choice of "failed as a man and as a son". Regardless of what he intended, those words probably shot right through him and likely caused him to stop reading the rest of the letter. Maybe you could have said "I am disappointed" or something... but the word "fail" has a really harsh judgemental effect

2) This is not about the letter, but about what you keep saying about DIL... "I lovingly pointed out some serious character flaws that he's taken on from his wife". I am dealing with this myself from your son's perspective. I know that my dad hates my fiance, and he brings it up every chance he can. He blames my fiance for MY shortcomings... and that's not fair. I am an adult and only I am responsible and accountable for my actions. If I mess up, I don't blame my fiance for it, and my dad shouldn't either. It pains me greatly when my dad does it, and he's obviously trying to drive enough of a wedge between us in order to get me to leave him. Look, I know that he doesn't approve of my decision and that you don't approve of your son's, but until he decides he wants out, your criticism of his wife is just serving to alienate you from them. It's not HER fault... it's yours (I'm praying you don't hate me for saying that). Why would she want to be around you when you obviously dislike her so much? Why would she want to bring her kids to see someone who obviously doesn't respect Mommy? Why would your son want to spend time with someone who pushes him to leave the wife who he seems to love and spend the rest of his life as a single dad?

Sept -- you know that I respect you so much and consider you dear to me. I hope you're not mad at me for saying this, but I feel I can share a perspective which may help you see his point of view.

I mean, there is no excuse for him borrowing money and then not finishing the tile work. None. But don't blame the DIL, and I know how resentful you must feel, but try not to use the word 'fail'. It's one of the ugliest words a parent can say to their child.

Please tell me if you think I'm completely off-base and need to mind my own business. Your friendship means more to me than this one particular issue.