My DH would say.."oh skid said to say hi" and I wait expectantly for some sort of positive response. When I had first disengaged I used to try and discuss the matter with DH and it would end up going wrong. However, then I changed my response and it had a really good outcome. When DH would say "oh skids said to say hi" I would reply "oh that's nice...now I've been wanting to speak to you about ..holiday/bill/renovation" - basically anything I could think of to change the topic and conversation. I think now that he doesn't get a reaction, he doesn't even bother telling me anymore. 

How about "you're right, I don't want to hear it," next time he says that.

I don't think you should care if you look like a b!tch to either one of them. Tell DH to stop bringing up his son with you - you will let him know if you ever feel ready to have a relationship with him again. And if he starts again, put up your hand and walk away.

As for the skid, if he writes to you, tell him to stop contacting you.

Some people need to be hit over the head with a big fat NO to hear it. I think you are being too nice about it.

I like that idea of "That was nice, OH! By the way, have you heard from___/ seen the thing in the news about ___/ gotten our credit card bill?"

Acknowledge the comment but --DISTRACTION! lol 

Keeps you from being the bad guy.

You have let your husband know where you stand with his son. He knows that you don't give a rats ass that his son says, "Hi". You know what he is trying to do. Tell him to stop.

If he won't stop telling you that his son said, "Hi" (I mean, really, who cares?), either ignore or just say, "Whatever," or anything you want, really. Don't worry about who thinks you are a bitch. You have every right to decide who you want a relationship with, and who you don't.

If SS writes you, throw it in the trash. You are not obligated to reciprocate to letters, to greetings, or anything else.

My SD28 has been trying to get my DH to see her now husband in a different light than the drug addict, thieving, verbally abusive ass that he is. She tries to tell DH stuff about him that she thinks DH will like or respect, or that they have in common. He flat out ignores, refuses to show any interest in the guy who once took a crap in SD's bathtub, called her a whore (in a busy, public place), and treats her like crap. Yes, after all of that, she married him.

If that makes DH an asshole, so be it. He thinks his daughter deserves better and will not condone this guy's treatment of her.

You have made it clear that you do not want a relationship with SS (and have good reasons) and your husband needs to respect that.

You're not obligated to be involved with any aspect of your H's messy low rent baggage. You tried, which was kind of you, and have chosen not to subject yourself to it anymore.

Now it becomes a matter of retraining your H and getting him to accept that this is permanent. It's not uncommon for partners to test boundaries, especially at first. They may seek to persuade us, try to bully, or assume we're just mad and will calm down eventually. If you're feeling harassed, then you should do something about it. You know your man best, so you'll have to decide the best way to remind him of your boundary. Changing the subject, ignoring, walking away, or reminding him of the boundary are all options. So is flipping the script and asking your SO why he wants to subject you to further abuse/pain etc. Just lather, rinse, repeat while remaining calm and factual for as long as it takes to get him to accept your new norm.

I disengaged after 18 years of overfunctioning and doormatting. Because I had been so accommodating for so long, all the parties tried to pressure me back into line. My H thought I was just in a snit at first - you know, emotional woman, she'll get over it, yada yada. I had to become a big brick wall, strong and impenetrable. I had to train myself not to rise to the bait when he would want to tell me things about skids or SILs. And it took him about a year to get it through his thick skull that I was truly done. I retrained him.

Stay the course. Visualize that brick wall, and you building it brick by brick. Be factual, keep emotion out of it, and be consistent. If you backslide, start over. This is how you create a healthier new norm.

This is one they never stop trying to do for some odd reason. And, you know good and well they most likely never said a word and if they did it was to probe for additional marital information only.

I have stated why is she asking, she does not care how I am....her years of horriific behavior clearly defines how she feels about me, cares about me or wants to deal with me in the future.

Why this is a favorite go to phrase I will never know... And, even more twisted is why they would continue the passive aggressive contacts.  Like a random thank you card (now you have not recevied a thank you verbal or otherwise in 12 years), and the list goes on. Funny, if you stay away, they cannot stand it either.  So they want you around to insult you more? Oh yes, to only make certain if you are around you know you are fully excluded as "family."

It cannot get any more dysfunctional than that, my thinking.

Its interesting how skids flip flop from hating, shunning, to wanting to be stepmom's friend all of a sudden. I played this game for awhile but like many others on this board will only engage according to my own comfort level now.  DH will sometimes tell me that skid says "hi."  I don't get overly excited or feel special that skid included or thought of me, I'll just say, "Hi back" or "that's nice." It generally doesn't go further than nicieties anymore.  Even though I'm disengaged there's always these tentacles trying to draw me in just so they can toss me out again.  It only works for them if you engage.  I'm fairly certain that I'm thought of as a cold b*tch at times because of my faint interest in their lives and removal of myself and my wallet.  But I don't care anymore. It was spelled out very clearly that they didn't want me in their lives in the beginning. I got the message and they got their wish!  

Your boundaries may need to be very firm at this time. You may need to tell DH that SS has a mother and a father and he needs to focus on a relationship with his actual parents. You can be supportive of his relationship with his son without actually being involved.  You're in a space where you need to protect your personal energy so be firm and let DH know that ss and his relationship is to be kept separate from your marriage.