When does healthy love become nothing but unhealthy obsession?

I don’t know how to say goodbye to you
I’m not good at things that I don’t want to do
— Sam Phillips, “I Don’t Know How to Say Goodbye to You”

I have no regret about any of the times in my life when I’ve fallen in love. Each woman who I’ve loved has meant something to me at that time in my life — and for reasons that were about her alone — so I cherish and honor each woman in her own way.

But I do regret how some of these loves have ended. It’s not so much that I regret things I did that were damaging or hurtful to others, but rather that I have a history of holding onto love that needs to be allowed to die.

I know how to love in ways that are deep and honest and healthy. What I don’t know how to do is to walk away from my feelings for a woman when it’s no longer healthy to love her. I’m never sure where the line is between loving in a steadfast way and holding onto something which is already dead.

And all this is wrapped up in childhood trauma about the mother who abandoned me.

Relationships die every day. In fact, most relationships die. The vast majority of times when two people fall in love with each other, the relationship is destined to end. People change their minds. Sometimes, their character and values get in the way. And other times, one or the other partner is simply dishonest and betrays the other.

So if most relationships are destined to die — meaning most love doesn’t survive — why is it so hard for me to accept this and move on? And what does this have to do with my mother?

I’ve told you about my mother before. She left us when I was 5 years old. She was in and out of my life for a few years after that. Then she was gone for good. By the time she was gone, I needed my parents’ marriage to be over. It had been a chaotic and dysfunctional nightmare to live through. They had fought all the time — and my father had used us as pawns in his attempts to manipulate us. I felt constant stress.

I needed emotional peace and stability that I never found.

My interpretation of that experience was that my mother abandoned me. She later told me that she thought she was doing the best thing for all of us, because she knew my father would never let her leave with us — so she feared that someone would end up dead if she didn’t give us up.

Even though I now understand her reasons for leaving, at the time I simply felt abandoned. The hurt went so deep that I felt numb about her for many years.

As an adult, I tried to have a relationship with her, but it was never right. She always felt like the immature child who never grew up. No matter what I did, I couldn’t find a way to allow her to become the mother I had so desperately needed.

It took me a long time to realize that the trauma of losing my mother left me with a terrible fear of being abandoned by women who I loved.

I’ve considered all sorts of ways of looking at how this has affected my relationships with women. To what degree am I trying to rewrite the abandonment script as an adult? Am I trying to find just the right woman — who I can love completely — who won’t give up on me? Maybe. I can’t be sure.

I just know that something inside of me holds on to love — and to faith and hope — long past the time when a healthier man would have given up and moved on. There’s a part of me which still wants to believe that I can win the love of someone whose love has become completely unavailable.

When we fall in love, it’s inevitable that there will be bumps in relationships. There will be times when each person hurts the other in some way. It’s healthy to be able to hold on during such inevitable periods of trial — and for the relationship to come out stronger in the end.

All that is true, but it’s also true that you can hold on to something for too long — something which is already dead. You can be delusional enough to be in complete denial. You can be past the point of faithful love — when you slide into the zone of unhealthy obsession.

But where is the line between loving determination and unhealthy obsession? I’m not sure I know.

One of the things that I’ve learned most clearly during my psychological development is that every single one of us is dysfunctional and unhealthy in some way. Some of us don’t realize where our dysfunctions are. Others have started to suspect certain things in us aren’t quite right. And others of us have managed to map quite a bit of the emotional damage we’ve sustained over time.

Every woman who I’ve fallen in love with has had some form of emotional damage which matches my own or is complementary to what I’ve gone through in some way. In most of these women, the damage has been hidden at the start, but it’s slowly revealed itself over time.

Few people like to admit they’re damaged, but it’s normal. Accepting the damage and starting to repair it is a major part of the process. Some get to that point. Others never do. Some start down that path but give up and run away. A relative few accept changes they need to make and become very different people.

We all have different paths toward emotional heath and maturity. It’s true that some never even get started, but even those who do can take long and meandering paths to get there.

When I love someone — and it appears that the love needs to die — I want to believe that this woman and I are each on paths of our own. Paths that will bring us back together. My unconscious fantasy is that for this woman to love me would finally show that I can win the love which had abandoned me — that I could finally believe I wasn’t worth leaving.

And no matter how much my rational brain tells me that I need to give up on this love, something in my emotional programming tells me to hold on. Something forces me to believe — in spite of all evidence — that this will be the time when there will be a fairy tale ending for both of us.

When I’m in the midst of such a struggle, I can’t tell where the line is. Even if my rational side tells me clearly to run away and never look back, something in my heart says, “Maybe it will be different this time.”

And my heart is stubborn.

I know that I should give up on love long before I do. I accept that there’s something irrational about continuing to feel love where there is no reasonable hope of being loved again.

But maybe I just like being unreasonable. And maybe there will come a day when my stubborn faith will be rewarded. It’s unlikely, but holding fast to unreasonable faith seems to be the only way I know how to love.