Carolyn: How does one re-establish a relationship in which both parties behaved very poorly, making so many mistakes that trusting one another is currently very difficult? Both people have grown such that they still love one another and feel terrible about the past screw-ups, but regaining trust seems impossible. When do you know that working on a relationship is a positive thing, and how do you know when you're basically flogging a dead horse?
A: Poor horse.
Whether your efforts will be productive or futile depends on where you're directing them. If you're both working to regain each other's trust, as you imply in your question, then I'm confident you're both doing your very best.
And, both wasting your time. We do not have it in our power to make someone else trust us. We can behave in a trustworthy manner -- or not -- and therefore deserve someone's trust -- or not. And you do at least suggest you're both tending to your own behavior, which is something.
But granting that, trust is always someone else's decision. So until you cease lobbying to get yourself off the hook and concentrate instead on letting the other person off, some beast is in for a flogging. Give trust vs. receiving, something that is in your power, always.
Think about it: Your partner screwed up, as you did. Either you believe your partner regrets that, as you do, and deserves to be trusted again, as you obviously feel you do -- or you need to acknowledge openly that your poor behavior was forgivable but the other person's wasn't. Meaning you either need to forgive and move on, or declare unforgivability and move on -- delighting horses, for sure, either way.
Don't gang up on friend
Carolyn: One of my closest friends is very judgmental. She spends a lot of time criticizing other people's actions but gets upset when people make comments about her that she thinks are critical and hateful. Several of our friends think we need to hold an intervention to make her aware how her comments hurt us. Any advice on how to do this?
A: First, all of you gather together, with her, at a neutral site. Then you talk about unrelated things. Then everybody goes home.
Then you speak for yourself only, on the spot, whenever your friend says a mean thing. Like, "I don't think you're being fair." Or, "Please don't be so quick to criticize." Or, "Back off, you biatch." OK maybe not that one.
If every one of you had the nerve to do this firmly, gently, consistently and with humor whenever you could, you wouldn't need to gang up on her at all, not even ostensibly for her own good.