I’ve had this kind of conversation before. Every time it is the saddest imaginable conversation, because at the end, in spite of great affection, both parties will be dead to each other. Alive and walking around in the world, and doing acts of kindness, and trying to be the best they can be, and dead to each other.

We don’t come to this kind of final conversation lightly. First of all, we have to care enough about the other person to extend them the final chance to avoid our mutual deaths. The average jerk who acts like a jerk and hurts us in a jerky fashion does not get this kind of final discussion. We just write them off, smile when we see them and avoid anything of consequence with them. But with people we deeply care about, who have deeply hurt us, it sometimes comes to this final conversation.

Personally, I tend to avoid starting these conversations once I’m fully aware of the hideous terrain we are both stuck in. Once the other party insists that nothing you have said changes anything, you are pretty much done. Words at that point have no ability to change the emotional reality that makes it impossible for us to continue as friends. In fact, if you express yourself clearly you are only making the wound deeper by seeming to blame the other person for being heartless, clueless, unforgiving, unyielding, rigid, needy, childish, etc.

The outline of this talk is always the same. The person calling will say they love you, that they have taken about all that they can take, that they have tried their best to be your friend and give you what you need but nothing they have done has been enough for you. They will place it on you, pronouncing the final death.

After all the aggravation, the soul searching, the health threatening stress of trying to find a mutual solution with somebody who is unable to overcome their righteous anger, their inability to forgive, words are of limited use. That said, it is good to remain honest until the end.

Trust me, you will get no acknowledgment of your honesty, and truly it means nothing in that moment. But you remain true to yourself by not pretending that all of your hard work has produced any tangible result. It is time to put down the cadaver of an old friendship you were carrying, alone, in hopes of a miracle.

I find that at the very end of these talks sometimes a last precisely calibrated insult can be very helpful in allowing your dear friend to permanently write you out of their life. At that moment, it is the least you can do by way of mercy.