Holding my boundaries is very tough at times. He said as he was leaving for work this morning "I don't know what to say or do that isn't going to make you angrier than you already are"
This is the 3rd or 4th time he has said something similar to this, I think. You may want to say next time "Look, I'm sorry and I'm trying to be civil here, but it's really not my job to make YOU feel better about the destructive choices you've been making lately. If this is awkward for you, that's your issue, not mine. In case you haven't noticed, this is very difficult on ALL of us, including the boys, so please don't ask me that again."