How could we take responsibility but avoid self-destructive shame?

I knew from the beginning that it was a bad idea to date Megan. It was three years ago. I had casually known her since she was an 18-year-old working at a fast food restaurant where I used to go.

By the time she got in touch with me and wanted to talk, she was 25. We met for dinner one night and she told me she had always been interested in me. She wanted to know if I’d be interested in dating her.

Megan isn’t anyone I would have ever pursued. She’s attractive and sweet. She has a wonderful heart. But she’s not the brightest person and her interests were very different from mine, to put it as nicely as I know how. She had also grown up among uneducated country people, so her accent and grammar were like fingernails on a chalkboard to me.

But I had been desperately trying to get over a woman who I couldn’t have, so I welcomed the opportunity for a distraction. I knew it was a bad idea — destined to go nowhere — but I agreed to try it.

It lasted for four months and I spent half of that time trying to figure out how to tell her this wasn’t working. I’m not very good at ending relationships that need to end. Despite her best efforts, I was bored to tears. Dating her was not only failing to interest me in somebody new, but it was also reminding me of why I had wanted someone else instead.

It was miserable for me and it wasn’t fair to her.

I eventually broke things off, but I handled it poorly. I wasn’t mean, but I just didn’t communicate the situation as well as I could have. I didn’t really want to talk with her about it, because I was afraid that my guilty feelings would cause me to back down instead of ending things.

The details don’t really matter now, but I still feel guilty about it three years later. Every few months, something will come up to remind me of her and I feel awful. I constantly think about how I could have handled it better. I know now — and really knew then, I suppose — how to handle it well. I just messed up. And I feel terribly guilty that I hurt her.

For the last few days, I’ve been thinking a lot about my feelings of guilt. I’m trying to figure out — not for the first time — how to strike a balance between two extremes.

Some people hurt others and never deal with their actions. In all sorts of relationships — friendships, family, romantic relationships, co-workers — they walk all over people and think nothing of it. Narcissists and various other dysfunctional people are in this category.

Others internalize guilt and allow it to turn into shame. I’ve always been one of those who experiences a lot of shame for things I feel guilty about. (I know why my childhood programming made me that way, but I don’t want to go down that rabbit hole here.)

Everyone has some things he’s done in life that he’s not proud of, but how many people internalize shame about things from their childhood that nobody ever found out about? That doesn’t seem normal or healthy, but I can’t seem to help it.

When I was a little boy, I would sometimes steal coins from my grandfather’s dresser. I never told anybody and I was never caught. It was never much money. He would have gladly given me the change. But for several years, I secretly skimmed his change when I could get away with it. There was a piece of art in their living room that had a hollowed-out area underneath the felt bottom. I would peel that fabric back and hide my stolen coins there until I could sneak them out of the house.

I still feel horribly guilty about that. I have no idea why I did it.

When I was about 12, I was visiting a friend who lived somewhere else. He was a trusted helper for the local high school football team. I was visiting during the late summer when pre-season practice had already started. My friend knew a secret way to get into the locker room after it was locked and the team was practicing.

Several times while they were away, we went through the pockets of players and stole change. It wasn’t much. We didn’t clean anybody out. It was just a bit here and there. We took our stolen money and bought cheap firecrackers and bottle rockets.

I felt guilty about what we were doing then and I feel even more shame all these years later. How in the world can I take responsibility for something like that? There’s nothing to be done about it.

Even if I wanted to track down the people from whom I stole and ask forgiveness, I wouldn’t know where to start. And even if I could find them, they would look at me and say, “I don’t remember that. Why are you bringing up something from the distant past like this?”

That’s at the heart of what I’ve been thinking about for the last few days. I think it’s important to take responsibility for the mistakes I make, but at what point do you need to just forgive yourself and accept that you were a different person, an immature person? And if there was someone who you hurt in some way, how do you know when you owe the person an apology and when it’s best to leave an old mistake alone? When is it worse to bring up the past for someone? Isn’t there a point at which you’re not doing anything positive for the other person — when it’s all about your own feelings of guilt?

There’s a romantic relationship which I had about 10 years ago in which I hurt a woman. It wasn’t intentional, but I hurt her by not ending a relationship quickly, as I should have. I knew it wasn’t good for me — there was actually someone I knew I should be dating instead — but I allowed it to continue for several years off and on instead of cutting things off quickly and sticking to what I knew was right for both of us.

That relationship ended badly. I don’t appreciate how she acted at the end, but I think I understand now that she was so hurt from keeping her hopes up for so long that she eventually had to do what she did. I still think she was wrong, but at least I understand.

I’d like to go back and apologize to her. I feel bad about how I handled the relationship. I’d like to explain myself. I’d like to tell her that I understand that I screwed up. I’d like to apologize.

But I know her well enough to know that she wouldn’t want to open that up again. I know she wouldn’t want to hear from me. So even though I have guilt about how I handled things, I know that making such an apology or explanation would be selfish — because it would really be for me, not for her.

And this brings me back to Megan. I don’t really think she was invested in me deeply enough for it to be worth opening that can of worms three years later, even if it’s just to apologize. But I wonder sometimes whether I’m giving myself an excuse to avoid an apology which I owe her.

I don’t want to be one of those people who runs over others and hurts them without caring. I’ve known people like that and they’re not decent people. But I also don’t want to live with guilt and shame about everything I’ve ever done which I regret — and I don’t know the healthy place to draw the line between the two.

In so many ways, I’m two different people on this score. I suspect most of us are. There’s a part of me which desperately wants to do the right thing — to be a moral and responsible person. But there’s another part of me which wants to take the easy way — to make excuses for myself and ignore my mistakes and the ways in which I might have hurt people.

I suppose I’m destined to have those two parts of me fighting each other for control, because each one can lay out a beautiful case about why his way is the right one.

I’ll never be perfect. I can’t imagine me stealing pocket change from people today and I like to think I’m mature enough now to end romantic relationships more quickly — and with responsible explanations.

But I’ll never know when I’m right and when I’m just making excuses for myself. Maybe there’s no way to be sure. Maybe the only thing we can do is to listen to both our selfish ego and to our guilt-ridden inner prosecutor. Maybe finding compromises between them is the only way to resolve any of this.

That way of compromise is messy, but it seems to be better than either of the extremes.