Verified by 
Dear Dr. Alasko: We have a relative who has a disturbing habit of always talking about the past and lamenting about all the things he should have done and how much better off he'd be if only he had done this or that. His constant harping on all his mistakes (and ours too) really bothers us. Why is he so stuck in the past? And how can we get him to be happy with what he has?
Dear Reader: Remorse and guilt, as one of my teachers said, is a total waste of time and energy. I've come to accept the wisdom of his words.
First, let's define remorse and guilt as patterns of thought that center around criticizing past events, assigning a conclusion of "wrongness" that remains permanent. By definition, in this way of thinking, it's not that you just made a mistake, you are a mistake.
I remember a male client who complained about how he should have married "Debbie." He believed his life would have been perfect if only he were with her. I challenged his assumption: "How can you be so convinced it would have been perfect?" He scoffed. "I just know it."
So from his position of "knowing it" he refused to seriously date anyone else because they could never compare to Debbie's fabulous (and, of course, imaginary) perfection.
Finally I said, "I believe you're being lazy and self-indulgent. You're indulging your fears about facing the future, so you just look backward, certain in how wrong you were, and still are. It's a coward's way to live." He didn't like that.
Remorse and guilt act like negative energy shields that protect you from taking risks. Living in the present takes courage. You have to meet new challenges directly, with your own energy and resources. You must also be prepared to learn from your new mistakes.
But when you're mired in remorse and guilt, there's no need to have any courage because you shy away from challenges.
So why is your relative stuck in the past? Because it's easier. It's a state in which everything is utterly predictable. He's being an emotional coward.
As for getting him to be happy with what he has? First, you can confront him, and you can also refuse to provide a forum for his negativity.
I suggest you take your relative aside and say, "I need to ask you a big favor. I want you to stop bringing up certain topics and how bad you feel about them. It's time for you to move on. I really hope you do. In the meantime, I'm really tired of hearing about the past."
Yes, you risk offending him. But you're also exhibiting emotional courage. You're doing something that’s difficult but needs to be done.
Finally, you might be doing him a big favor. It's possible he'll be shocked and run off and pout. But your words might sink in, and he'll possibly have an awakening.
What's certain is that if you do and say nothing, he'll keep on being stuck. And you'll continue to be irritated. Take a chance and do the right thing—for both of you.
