Letting Go: Ending a 45-Year Friendship

Recently, a friend [for over 40 years] sent me several audio messages. He was seeking some guidance, a response, maybe just feedback — regarding a decision that he and his partner are in the process of making. Or perhaps have almost made but aren’t quite 100% sure about yet. They’re just looking for another point of view.

By the way, my friendship of over 40 years is deeply meaningful and profoundly impactful for both of us.

The story is this: the two of them have been friends with another couple for over 45 years. A long-standing friendship that has lasted through various stages of life, with all the expected ups and downs.

Sometimes they didn’t see each other for long periods, but the connection kept going. You know how it is — maybe you keep showing up for the friendship because there’s just so much history.

But now he and his partner are at a crossroads.

“We want to break up with them.” I heard him say. That’s the term he used. And it struck me: how do you do that? How do you break up with friends? How do you un-know someone?

I mean, is it even possible? Is there a respectful way to step away from people you’ve shared decades with — people who were once central to your lives? Or does it always come with guilt, with second-guessing, with the ghost of shared memories followed by the fact that you have not deleted them from your contact list?

They’re about to do it — to have “the talk.” And my friend just wanted to hear someone else’s thoughts before taking that final step.

And honestly, I get it. Because people I thought were my close friend have broken up with me. One outlier is that he wants to write them a letter—they live in the same neighborhood… more on that later.

CAVEAT: This blog is stitched from two threads. One speaks with reason, the other with feeling. The rational and the emotional wind their way through the text, weaving a tale that drifts between order and intuition— a tapestry of thought, if you please, out of sequence, yet deeply entwined, rooted in memory at the convergence of possible futures.

Literally Walked Away

People have literally walked away from friendships with me. I’ve never done that to anyone in my entire life. Yes, I have broken off with people, but they are more than friends - some even live-in girlfriends. But I have never-ever, broken it off with a friend.

Sure, I’ve experienced friendships that slowly dissolved—because of time, distance, or a fading connection. Those just kind of… trickled away. Like a dripping tap over a couple of years, and then one day, someone quietly turns it off. Not because of any big falling out, but because the flow just stopped. I have a few of those. They’re sad, but understandable.

But this—this has been different.

People have specifically said to me: Don’t call. Don’t write. Don’t text. This friendship is over. I don’t want to see you anymore. Goodbye. Click. Done. It’s a weird feeling to have that done to you—especially when you’re left wondering why. It puts you in a deep state of reflection. One of the deepest that I ever had, that’s for sure. 

The first time it happened to me, I felt like a child whose pet hadn’t come home one night. But the pain went deeper — more like someone had cut off my right arm and left leg. It was all so new and raw back then, and even after six years, its essence still lingers. My heart keeps threatening to reopen, called upon by a stubborn hope for reconciliation and a renewed connection.

Sometimes, sure, I know why. I get it. I can say, “Yeah, I know what I did,” and I feel remorse. I’ll own it. I’m sorry. And in those cases, maybe it’s for the best. Good for them. But many times, I’m left confused. Wait a minute… what? 

I thought we were friends. I thought we were good friends. 

I liked our friendship.

We shared our lives. 

We spent time together, cried together, laughed together, partied, grew up—and became adults. And I always thought our friendships would ebb and flow, the way friendships naturally do. I looked forward to growing old with some of these people. Yet one day they're with you, and the next, they're gone—abandoning the sphere, walking away from circles, and severing the connection.

Several of my male friends, in particular, have distanced themselves—and that’s been especially hard. In these later years, male companionship matters more 

than ever; it’s when you truly need each other. I was genuinely looking forward to that. 

Now I know who those men are. They’re a small group of individuals I deeply respect and have long turned to for counsel—and they, in turn, have looked to me. They’ve been a wonderful source of support and inspiration.

But the real sadness hits at that moment when I think, “Where is my best friend?” He’s not here. The only one who really mattered—was him. I love and respect others, of course.

But when your best pal chooses to walk away from your life and tells you to fuck off—that’s the bottom of the second bottle, right there.

That hurt cuts through the safety frequency of my almost-old-man life.

Does he not miss me? Does ever wonder how I’m doing— or if I’m out here thinking of him, just to feel that thread, that flicker of connection we once had?

But he deleted it.

Erased the line.

Like it never mattered.

That’s the source of the pain. I just realized I was delusional about the actual dynamic of our friendship—he saw me as a friend, but I saw him as a brother. Damn! How could I have gotten it so wrong?

The Need for Male Companionship

I need male companionship now more than I’ve ever, ever needed it. Not in a sexual way—just honest, real companionship. A buddy. A friend. I miss that deeply. I had that with someone for over 50 years.

Yeah. A 50-year friendship—gone, just like that. And not just him. A few other close friends I’d known for 10, 15, even 20 years… also gone. Just disappeared from my life. No big fight, no huge fallout—just silence.

Now I’m 61. And here I am.

Sure, I have some friends, but nothing local—no one I can just grab coffee with, go for a walk, or hang out with on a Saturday. There were a couple of guys I knew where I now live, but those were newer friendships. They didn’t feel fully rooted. More like friendly acquaintances from work or old connections through our families because we all had kids or we liked pints, 8 Ball, on TGIF night’s.

One of those guys—his marriage ended right before mine did. We stayed connected after that. We did the occasional dinner or BBQ or a bar from time to time, trying to keep the friendship going in a new context, post-marriage. But it didn’t stick. I never really knew what he wanted from our friendship. He always seemed a bit awkward around me, though I thought we had something good. That’s gone now too.

But I didn’t end it. I didn’t say, “Don’t call me anymore” or “Goodbye.” I just stopped reaching out. And he stopped texting. That was it. You wait. You wonder. Just be still and watch what happens. You hope something shifts. But it does or it does not. 

Back to the central story. A very Dear friend of over 40 years asked me

Recently, a friend confided in me that he’s considering ending a couple of long-term friendships. He asked for my perspective—knowing I’ve been on both sides of that experience. I felt honored that he invited me into something so deeply personal.

What struck me was how meaningful that moment was.

The longevity of those friendships—the weight of that shared history—isn’t something you discard lightly. There’s something profoundly human about wrestling with the story of a friendship that’s spanned decades. And perhaps even more human to invite someone else to bear witness to that struggle.

It’s an incredibly, incredibly long story. A friendship is about to come to an end—for a variety of reasons. But those details aren’t really important for this particular blog. The reasons behind the breakdown, the slow erosion, and ultimately the final dissolution of the relationship don't matter as much. 

That’s not meant to suggest that this issue isn’t serious or unworthy of being taken seriously. The fact that my friend asked me about it—and knowing who he is—I understand that it’s very important to him. It’s something that deserves thoughtful processing and shouldn’t be decided in isolation.

What really matters is the idea of taking action—making a decision like that, you know? So I want to share a few things I’ve been thinking about, and I’ll outline them here.

First Things No Always First

The first thing I suggested was this: it’s not about victim-blaming. It’s more about being accountable. If you’ve been in a toxic friendship for years—ten, twenty, thirty, even forty—and you’ve just gone along with it, never really calling out the hurtful things your friend may have said or done, then there’s something to examine there.

Maybe you brushed it off. Maybe you thought, Oh, that’s just how they are. Maybe there was too much wine at dinner parties or too much laughter masking real hurt. And over time, that dynamic becomes normalized—it turns into an acceptance of toxicity and possibly bullying bordering on intent to harm and patterns of abuse.

If you go along without ever saying, “Please don’t talk to me like that,” or “That really hurt”—without setting clear boundaries early on—the friendship can drift unchecked. Then, when things finally unravel and you say, “You did all these things,” your friend may genuinely be confused: What? You never said anything. From their perspective, it doesn’t feel entirely fair. Why didn’t you just tell me? they might ask.

Avoiding that outcome requires being conscious of—and owning—your part in how things turned out. That self-reflection is the hard part.

Reporting Abuse: I am not referring to abuse—if that is happening, go to the nearest hospital for immediate medical assistance and report the abuse to the authorities, regardless of what country you're in. Document everything—text messages, pictures of injuries, diaries of emotional abuse in the moment, and so on. Get help now!

I will say that I definitely regret not doing a better job of managing my own consent and boundaries. I had few boundaries, still don't have a lot these days too, and the ones I did have often seemed to cause more harm than good—mostly to myself. I think that's part of why I’ve become a loner. I can connect with people quite quickly and have a certain charm, but after spending time together—maybe a few hangouts, or even months or years of friendship—I seem to lose traction in the relationship.

Without any real connection, people just slip away. Then I get added to a group chat—maybe for a party. At first, I’m in the housewarming group, but before long, I find myself on the outer edge, then outside altogether. Eventually, the group is deleted. No more invites.

My solo life is a choice—not because I dislike people, but because I’m more drawn to one-on-one friendships than to groups. And those connections are rare and difficult to maintain, especially since most guys seem to prefer running in packs—a tribe. The "solo tribe" is a rare breed. The irony is inescapable.

I spend a lot of time enjoying my freedom while also trying to understand this paradox: craving companionship yet clinging to solitude.

I’m perfectly content to wander down to the local pub on a Saturday afternoon with one or two friends, share a few pints and some food, and then wobble home after four or more. But invite me to a "boys’ night out" in the back soi's of Bangkok—those infamous bars where the skin is soft and young and... well, you get the idea—and I’m out. That scene isn't for me. I stopped going to those nights a few years ago.

I went to a good friend’s stag once, in Bangkok, and it turned into a whole weekend of that kind of thing. I didn’t handle myself like a gentleman—not because I’m not one, but because that tribal energy is so far from my natural vibe that it creates friction and tension the whole time. The triggers are just too hard for me to resist. I’ve got my fingers on all of them, and I pull the trigger more times than is tolerated. Then I become the annoying voice of reason in the room—and just like that, we know I am not a fit - I’m out.

So, I decided: never again.

I don’t initiate or invite or organize things—I wait on the sidelines, fingers crossed, hoping to be invited into the inner circles. But the truth is, I have to create my own inner circle. And that’s a life skill I don’t yet possess. I do try to find solo indies...again, the irony.

Can I learn it? Probably.

Do I want to leave the sidelines to learn that skill?

That’s the real question?

The Parts of Friendship - Matter Most

It also raises another question: which parts of the friendship matter most to you? At any age or stage, regardless of the dynamic, if you find yourself thinking, maybe this friendship isn’t working, and you’re leaning toward ending it or letting it fade, you need to decide how you’ll do that.

Start by examining the relationship itself:

• Is there one specific aspect you dislike? Maybe it’s a single recurring issue that could be addressed with an honest conversation.

• Or has the friendship become too hard to enjoy? Sometimes the negatives accumulate over time—what was once tolerable, like an occasional personal remark, may now feel unacceptable.

  
  

You know, maybe you were a little critical of me—like when I smoked pot in front of you at MY cottage, or when it came to my decision to live overseas. It feels like you've forgotten the great times we had in high school, getting high together and listening to The Moody Blues. Now, your harsh judgment of my choices seems unfair, especially after all the years we spent together.

And honestly, I get it—those things can be hard to accept. But here's the thing: you're outspokenly homophobic, and yet in that same conversation, you are elegantly virtuous about social justice. The contradiction is hard to ignore. 

One time you blurted out…” all she needs is a real man, one night with me and she would not be a lesbian.” I heard that hard, and one of my roommates and later a lovely friend, is a lesbian - what an odd thing to say knowing that you know I have many gay and lesbian friends.

But if that’s all our relationship boiled down to, just those criticisms, then maybe it wasn’t enough to keep us connected. Because there were so many good moments, too. We spent time together, shared laughter, did things we loved. We had a real bond. But maybe, on a deeper level—whether emotionally or intellectually—we just didn’t quite fit.

When I think about the friend who ended our 50-year friendship, I realize he was definitely on a different level intellectually. He was smarter than me, no question. 

But I kept pushing myself academically. He never finished his undergrad and struggled in university. Meanwhile, I managed to get through two undergraduate degrees and one graduate and post degrees—and I did well. Even a USA Ivy league school was happy to have me on board for post graduate work.

But it wasn’t always like that. Back in high school, I barely got by. My first year of college was brutal—I was asked to leave. I hated school. I wasn’t good at it, and I felt lost. So yeah, maybe I wasn’t perfect. But I was trying. I was fighting my own battles in silence.

In Grade 12, my best friend’s mother took me in, so I had a reasonably safe place to live. It wasn’t easy being there—there was a lot of yelling and fighting between the brothers and their mother and each other. Most of it was harmless bantering, but the real fights… those were hard to forget. It was a loving but very loud house.

Later in life, in my mid to late 20s, I started getting better at understanding that I’m actually a good academic. I started approached learning a little differently. I approached it from an emotional state rather than an intellectual one, and that changed everything for me.

I am seeing clearly that one can possess information, approach life and solve problems and make decisions from several single and/or blended points of view (POV). Different approaches to thinking such as: Emotional POV, Dictatorial POV; Intellectual POV, Spiritual POV, Blended POV, Multi-Vision POV, and so on.

What is There? Be Still Inside

I think when you look at a friendship, it’s important to understand what is there, whether it’s really compounded, and to try to get to some of the deeper emotions that might be present. You don’t have to make a big drama or announcement about it. You can simply make it clear that you want to cultivate the parts of that friendship that matter to you, the parts that are still there, and let go of the rest. 

If I were a gay man and my best friend had been openly homophobic, it’s unlikely our relationship would have lasted—maybe. I’ll never really know. I’m fairly certain he had enough sense not to be that vocal around the gay community or my gay friends—one of whom was the second-best man at my wedding. 

I assume that only because I never heard him make any homophobic remarks—except during private conversations, just the two of us out on the deck. At those times, I know he’s aware that I have gay friends, and therefore he’s attuned to the fact that his comment is also a jab at me.

I have a friend who sometimes visits the city where I live. Sometimes he tells me when he’s here, and sometimes he doesn’t. I know this because he’s told me before. In my mind, I think, why didn’t you tell me you were here? I would have loved to see you.

But he explains that when he’s here on business, he just wants to come and go quietly. He doesn’t want to see anyone. Slip in and out anonymously and privately. I understand that feeling. Sometimes he just wants some solo time.

Other times, he comes with his crew, and they want to hit the nightlife — bars, staying out till 4:00 AM, basically having fun in their own way; they like to have arguments with the sidewalk and debate with the curb. If he’s here for that, I might see him briefly in the early evening, and then we catch up one-on-one.

Or sometimes I don’t see him at all because that’s not my scene, and I don’t want to be part of that game. That’s his thing, and I respect that. It was never about the high cost of a boy's night out in the bars— it's about the high cost of making enemies within a good friend’s tribe. That cannot happen.

It’s understood between us, and we really care about each other. I even went to see him in Laos once — it was a great visit, really nice, perfect. That’s the kind of friendship it is. And I like that part of our friendship. I like that we can see each other when we can, when we want, and it’s always a nice time. It’s kind of like seeing a brother, honestly.

When I went to see him, he was a tiny bit upset that I didn’t stay at his house. I know I didn’t hurt him, but he was like, “Why not?” Because that’s what we do. And thinking about the time when I invited him to Bangkok with his now wife—fiancé back then—I said “you could stay with us. But you said, “Oh no, it’s okay, we’ll stay in a hotel.” So, I thought you were fine with it, especially since I wanted to stay in a hotel with my fiancé-to-be. But he seemed a little offended.

Next time I go there, I’ll stay with him because that’s what he likes. It’s family that way, and I take that as a compliment. Alright, moving on from that—

Next Thing Next - the end of the whole friendship?

The next thing I was thinking about and advising my friend about is to figure out if it’s the end of the whole friendship or if it needs to be clear about what it is. If it’s a widespread, compounded effect, maybe it’s over. But maybe they’re just annoying you because they have a little bit of a problem—like maybe they’re a little bit racist, or a bit homophobic, or they say weird stuff sometimes. Like, if they believe in UFOs or say the Reptilian race are running the planet—that’s just goofy nonsense, right?

Don’t take the beliefs of alien forms too seriously. Issues like homophobia and racism should be examined carefully—if someone’s position is causing harm to you or to others, that’s your first signal to pause and reassess your own beliefs.

It’s like having one of those eccentric friendships—and that’s cool. I like friends like that. I enjoy having unusual people around, people with strange or different beliefs. I find it fascinating and exciting. I love it when someone doesn’t share my views, because to me, that makes for a vibrant, attractive kind of friendship.

How Do You Un-know Someone?

Honestly, I don’t think you really can. There’s no step-by-step guide to un-knowing someone. I’ve known people for an hour, and others for fifty years, and I still think about them. I still know them. They’re still part of my life—part of my story. Who they were is woven into the timeline of my life.

They existed, and that mattered. And I take that seriously. Maybe too seriously. I think a lot of people don’t live consciously. Most are just surviving—but not even aware that they’re in survival mode. It’s just the default setting: pay the bills. Until the next thing.

How do you un-know someone?

I don’t think you really can. 

There’s no real way to un-know someone. 

After death we do not know if we'll know or unknow - well, anything.

I don't know that either.

Postscript: here's a direct copy of the audio message that sent to my friend after I published this blog:

Hi—just a quick follow-up. This topic has really stirred up some powerful memories and thoughts for me. Honestly, it’s what I needed. I know what you’re going through is difficult, and I don’t want to come across as self-centered, but your story has reignited a part of my past that I’ve been avoiding for a long time.

I’m not trying to draw meaning from your pain—I hope it doesn’t come across that way. It’s just that something in what you shared unlocked something I’d tucked away because it was too painful to deal with. And now, I find myself feeling ready to face it, which brings a strange kind of gratitude.

I’ve been writing about it—it’s messy, a bit all over the place, and I’m still trying to piece everything together. It’s a bit of a ramble as I work through it. Once I finish the blog post, I’ll send you the link. Maybe it’ll resonate, maybe not—but I just wanted to share where I’m at.