When do you stop being a supportive friend?

You must extract yourself from the role of go-between. That is not a safe place to be. It is possible that you can salvage your relationship with one or both of these folks, but unfortunately it is not too likely. However, neither of them will thank you for advocating for the other, and you do not want to take sides. I was caught right there between my parents, at the age of 25, and finally said to them, “You got into this by yourselves and you are going to have to get out of it by yourselves.”

I’m sorry. It’s hard. But it’s necessary for your own well-being. You no longer have a friendship with them. You have either a courtroom or a therapy session.

This is a very difficult situation. I have to ask if you believe she is capable of harming the child? (or is he possibly trying to play you against her?) If you think she may be violent, then call your local Child Protective Services if the child’s father will not.

Beyond that, I agree that you have to wash your hands of it and walk away. They are co-dependently addicted to their drama, and only a clean break or intense counseling will change that.

You need to understand that as a friend, you need to learn when to stay out of the way.
The best advice may be to wait on the sidelines and offer help only when one of them comes to you.

Your first responsibility is to the child. If you think the child is in danger, contact the authorities. (Or, you can go to the couple and tell them what you are going to do.)

In relation to the couple, you have done what you can, but it sounds like your good intentions at support and counseling are falling on deaf ears. It sounds like they have some real problems possibly some substance abuse issues

Go over to their house some Sunday afternoon when things are calm and tell them you are done being in the middle. You love em both, but they are adults and need to resolve their struggles themselves. Tell them you will be waiting at the other end when they work through their issues, but until then, it is up to them to get through their problems themselves.

As Monty Python would say, “Run away, run away!”

Of course you can draw the line at having friends who engage in violence.

Tell your guy friend (if you want to keep him) that you hope for his sake it is over, but you want to wait a while to see.

I think your values are wonderful and quite admirable. Do as you suggested: make it clear that you are no longer interested in dealing with or hearing about their relationship problems. And stay away. If you find that they did break and sufficient time transpires to convince you of its permanency, consider re-establishing your friendship with that great friend….you have quite a few years and probably some pretty good times between you. See ya….Gary aka wtf

All three of you as adults have been participating in this dysfunctional dance of your own volition. The only true innocent is the child who wasn’t given a choice.

By extricating yourself and being frank with him you may be able to be a voice for this child. They are both so wrapped up in their narcissistic chaos that no consideration is given to what this is doing to this child.

He is the childs parent and it is his primary responsibility. The danger is not just the possibility of her doing physical harm to the child which they can easily dismiss as being far fetched. The plain fact is that even if neither ever lay a finger on him he is being irreparably damaged just by witnessing this constant verbal violence as well as the physical.

Someone needs to give this guy a wake up call as Dr. Phil would say. Perhaps that could be you. I’ll also shamelessly borrow another one of his most frequently uttered truths, the effects of which I have personally witnessesed numerous times during my time as an Elem. Teacher.

“when you fight in front of your children, you change who they are.”

That’s a very powerful statement and this guy, as the childs Father, needs to face up to his responsibilities in this regard. Hopefully as a long time friend you can drive this point home even as you are exiting the situation. Perhaps that will help open his eyes if a long time friend such as yourself has the guts to tell him the hard and painful truth. Obviously he hasn’t been willing to get out of this relationship for his own sake but perhaps seeing it through the eyes of his child will shift his priorities to get the help they so desperately need. And if he can no longer use you as a substitute for a therapist may get him to look for a competent therapist who can help to mitigate the emotional damage done to this child before it’s too late.

When there’s no longer mutual respect and communication becomes violent.

I grew up watching similar scenarios between my parents, but was never able to say anything to anyone, because I was too young. If possible maybe try talking to that child to see how they might be feeling and aside from that I agree with @Buttonstc, this man needs to summon up some strength from somewhere otherwise he does not deserve to be a father. Maybe you being straight with them is what it will take.