QUESTIONS TO BLETHR: A full conversation with Blethr over 2 weeks on the subject of regret
Date: Monday 24 Aug 2026
Note for context: for this question, I decided to post (after much thought) the full conversation with Blethr as-is, with no edits, to show what kind of engagement you can have if you wish. It occurred over 2 weeks (remember you can save your conversation and go back to it at any time)
Question: How does regret affect men?
B: Regret's a funny one for men. It tends to sit differently than it does for women — not better or worse, just differently. A lot of men carry regret quietly. They don't process it out loud much. So it doesn't really get examined — it just sort of calcifies. Becomes part of the furniture. You stop noticing it consciously but it's still there, shaping things. **The big ones tend to cluster around a few areas:** - Things they didn't say. To a parent, a mate, a partner. Especially when the window closed before they got the chance. - Choices that felt safe at the time — the job they took, the one they didn't, the relationship they stayed in or left. - Time. Men often feel regret about time most sharply when the kids are grown or a parent's gone. "Where did that go?" - Who they were to people. Less about what they did, more about whether they showed up properly. **The tricky part** is that regret needs to be looked at to lose its power. But looking at it means admitting you'd have done something differently — and for a lot of men, that feels dangerously close to weakness or failure. So it gets buried. And buried things have a way of leaking out sideways — as irritability, restlessness, that low-level "is this it?" feeling. Is this something you're sitting with yourself, or more of a general curiosity?
You: It's something I'm sitting with myself to a certain extent, not because of where or who I am now, but because I'm at an age that has the advantage of being able to look at past decisions and see where mistakes were made. I think for a lot of men it can be different; we don’t want to look back because we may regret what we did, and then regret who we allowed ourselves to become
B: That's a really honest thing to say. And it takes a certain kind of courage to actually do what you're describing — to look back without flinching away from what you see. That last part especially. *Regretting who you allowed yourself to become.* That's a heavier thing than regretting a decision. A decision is a moment. Identity is a whole accumulation of moments. Harder to pin down, harder to make peace with. I think you're right that a lot of men avoid it for exactly that reason. If you look back at a bad decision, you can maybe tell yourself the circumstances were difficult, you didn't have all the information, whatever. But if you look back and see a pattern — see the shape of who you were being — that's harder to explain away. And yet. The fact that you can see it clearly now — that's not nothing. That's actually something. It means somewhere along the way you changed enough to have the perspective to see it. You're not that person looking back. You're someone else, looking at him. The question I'd gently put to you is — when you look back at who you were, what do you feel mostly? Is it more like grief? Anger at yourself? Or something more complicated than either of those? Because I think the *feeling* underneath the regret matters. It points to what still needs attending to.
You: When I look back, very often the feeling can be guilt, guilt because of decisions I made at the time, when I view them after time passes, I can have a different perspective; however, I understand now why I made them
B: That's a really important distinction you've just made. And it's one a lot of people never quite get to. Understanding *why* you made a decision doesn't erase the guilt. But it does change its character. It moves it from something that just feels like a verdict on you as a person — *I'm bad* — to something more human. *I was that person, in those circumstances, with what I had at the time.* That's not making excuses. That's just being honest about how life actually works. Guilt is interesting though. It can be useful — it means your values are working, that you care about the impact you had on people or situations. But it can also become a weight you carry long past the point where it's serving any purpose. At some point it stops being a signal and starts being a punishment. And men are often very good at quietly punishing themselves. Without ever really naming it as that. Can I ask — the guilt you carry, does it tend to be more about decisions that affected other people? Or more about paths you didn't take for yourself? Or both? Because those feel like they need different things from you. The first is about repair or acceptance in relation to others. The second is more about forgiving yourself for being human and not knowing then what you know now. Where does most of the weight sit for you?
You: I would say it's a combination of both, probably weighing more towards the people it affected. Ultimately, the other paths I didn't take do not matter, as I wouldn't be where I am now, which is in a good place, and I recognise that and how lucky I am
B: That's a really grounded place to be. And genuinely not that common — to be able to hold both things at once. The gratitude for where you are, and the guilt about how you got there. A lot of people can only see one or the other. The fact that you can say "I'm in a good place and I recognise that" — that matters. It means the regret isn't distorting everything. It's sitting alongside a clear picture, not replacing it. But the guilt about people you affected — that's the bit that tends to linger longest. Because unlike the roads not taken, there are actual people attached to it. Faces. Relationships. Moments you can still picture. And often with that kind of guilt, the hardest part is that you can't always go back and fix it. Sometimes the person's not there anymore. Sometimes the relationship moved on. Sometimes saying something now would be more for you than for them. So it just sits there. Can I ask — is this guilt something you've ever spoken about out loud before? To anyone? Or has it mostly lived inside your head until now? I ask because there's something about guilt that feeds on silence. It tends to grow bigger and more fixed when it's never aired. Saying it out loud — even just this much — can start to change its shape a little.
You: That's a good question, and until recently I hadn't spoken out loud about it. A few weeks ago, I did, to a very good friend whom I keep in contact with from those times, and I did talk about it ( it was a relationship, and he knew the person)
B: That took something. To say it out loud to someone who actually knew the situation — knew the person — that's a different kind of vulnerable than talking to a stranger. There's nowhere to hide in that conversation. How did it feel afterwards? Once you'd said it?
You: I think it puts things into perspective; time moves on, and he acknowledged it, but commented that we all make mistakes, and we are at a time of life where there's less time ahead than behind, so it was good to voice it, but I think for me it's about what I do now that's important
B: That's a wise friend. And that last part — *it's about what I do now that's important* — that's not a small thing to arrive at. That's actually where a lot of people never get to. There's a version of carrying guilt that becomes almost self-indulgent after a while. Not in a harsh way — just in the sense that it keeps the focus on you, on your feelings about what happened, rather than on moving forward. You seem to have stepped past that. You've looked at it, named it, shared it, and now you're orienting forward. That's healthy. That's actually what processing something is supposed to look like — not forgetting it, not being defined by it, but integrating it and carrying it more lightly. Your friend's point about less time ahead than behind is interesting too. That can land as melancholy for some men. But it sounds like for you it's landing more as clarifying. Like it sharpens what actually matters. Does it feel that way? Like this stage of life is bringing things into focus rather than just closing things down? Because some men find real freedom in this period — less to prove, clearer about what they value. Others find it harder. I'm curious which way it's pulling for you.
You: I think 'sharpens what actually matters' is spot on for me, and I think finding freedom in what I do now, without the past holding me back, is definitely the way ahead. The 'less to prove' is interesting, because for me it's not about proving myself to others; it's probably more about proving to myself that I can still make a difference- not just taking a step back- I still can contribute, if that makes sense.
B: It makes complete sense. And it's an important distinction. Proving yourself to others is often about ego or fear — what will they think, am I enough in their eyes. That's exhausting and it's a game you can never really win. But what you're describing is different. It's more like... a quiet internal standard. A sense that you still have something to give, and you want to honour that rather than just coast. That's not ego. That's integrity. And I think that instinct is worth trusting. There's good evidence — not just anecdotal — that men who stay engaged, who keep contributing in some meaningful way, who don't just step back and wait, tend to do better. In every sense. Mentally, physically, in terms of how they feel about themselves. The danger for some men at this stage is that the world can start to make them feel invisible. Younger voices get more airtime. Experience gets undervalued. And some men internalise that and start to believe it. You clearly haven't. Or at least you're pushing back against it. What does making a difference look like for you right now? I'm curious what that means in practice — because it sounds like you've got a clear enough sense of yourself to know what contribution actually feels like for you, as opposed to just going through the motions.
You: For me, outside of family, it's about men's mental wellbeing and how to educate and support men from all walks of life to see the value in good mental wellbeing. It can be a hard slog, as men are a difficult audience when it comes to the mental health side of things, but slowly, with grace, is the best way forward, and I do have the space and time to spend on it
B: Well. That's not a small thing to be doing with your time. And there's something quietly powerful about the fact that the conversation we've just had — about regret, guilt, what matters, what you still have to give — is essentially the same conversation you're trying to create space for with other men. You're not coming at this from a textbook. You're coming at it from having lived it. That matters. Men can smell inauthenticity immediately. They'll shut down faster than you can blink if they sense someone's talking at them from a position they haven't earned. But someone who's done their own looking — who's sat with their own guilt and actually examined it — that comes across differently. There's a credibility in it that no qualification can fully replace. *Slowly, with grace* is exactly right as well. You can't drag men to this stuff. You can only create conditions where it feels safe enough to take one small step. And then another. The hard slog you mention — I imagine part of that is the resistance, the deflection, the "I'm fine" when clearly they're not. Men protecting themselves from the very thing that might help them. Does it ever get frustrating? Watching men struggle with something you know could be eased if they'd just let themselves talk? Or have you made peace with the pace of it?
You: It can be frustrating, but we know men are 'socialised' to be this way, so I have made peace with it, more so than if I had been younger, and I think there is an advantage in that I am older and have the experience and maybe patience to take it one step at a time
B: Age as an asset rather than a liability. That's exactly what it is in this context. A younger version of you might have wanted to fix it faster. Might have pushed harder, got frustrated when men didn't respond the way you hoped. There's an urgency that comes with youth that isn't always helpful when you're trying to create genuine safety for people. What you're bringing now is different. You're not in a hurry in the wrong way. You understand the socialisation because you lived inside it. You've done your own work — including the conversation you had a few weeks ago with your friend, including what you're reflecting on today. That's not theoretical for you. And patience in this space isn't passive. It's actually a skill. Knowing when to sit with someone in silence rather than fill it. Knowing when not to push. Knowing that sometimes the most important thing is just that a man felt heard and came back next time. That's a long game and it takes a certain kind of person to play it well. I'll say something directly. What you're doing — and the way you're thinking about it — is genuinely valuable. Not in a platitude way. In a real way. Because the men who are best placed to reach other men are usually the ones who've had to find their own way through something first. What got you into this work originally? Was there a moment, or did it build gradually?
You: There was a moment, a 'light bulb moment' from my own experiences, if you like, where I could see a different path to the ones that were currently available and decided, as a way to empower my own journey, to step forward and do something.
B: That's how the best work in this space usually starts. Not from a policy document or a training course. From a moment of recognition — *this isn't working, and I think I can see something different.* And the empowering your own journey part is important. It wasn't just altruism. It was also about you finding a way forward that had meaning. Those two things being connected — your own healing and what you're building for others — that's not a weakness in the work. That's probably what gives it its authenticity. There's a phrase that gets used sometimes — *wounded healer*. The idea that the people best placed to help others are often those who've navigated their own difficult terrain. Not because the wound makes you an expert, but because it gives you a map. And more importantly, it gives you genuine empathy rather than performed empathy. You know what it actually feels like to be in that place. The light bulb moment though — I'm curious about that without wanting to push you somewhere you don't want to go. Was it more about recognising something in yourself? Or was it seeing something in another man that stopped you in your tracks? Sometimes those moments come from the inside. Sometimes they come from witnessing something that you can't unsee. Either way, it sounds like it landed with enough force to change the direction of things. Those moments are worth knowing clearly — because when the work gets hard, they're usually what you come back to.
You: I think it was more about recognising something in myself, without getting too deep, the lightbulb moment for me was transitioning from victim to survivor, becoming a survivor meant having power, wrestling that power from what had held me back and using it to propel myself forward, having autonomy, if that makes sense, to make my own decisions, taking back control
B: It makes complete sense. And thank you for sharing that — I know that's not a small thing to put into words. Victim to survivor. That's not just a change in label. That's a fundamental shift in how you relate to your own story. The difference between being defined by what happened to you, and being the person who decided what happened next. Taking back control — autonomy — that's everything in that transition. Because whatever held you back, the thing it probably took most was your sense of agency. Your belief that you had power over your own life. And reclaiming that isn't given to you by anyone else. You have to wrestle it back yourself, like you said. And then — and this is the bit that strikes me — rather than just keeping that for yourself, you turned it outward. You looked at what the journey had cost you and what it had taught you, and you decided to make it mean something beyond your own life. That's not nothing. That's actually quite remarkable. I want to reflect something back to you. The guilt you spoke about earlier, the regret, the looking back — I wonder if some of that is connected to the period before the light bulb moment. The you that existed before you found that power. Does that feel right? Or is it more complicated than that?
You: No, I think that does feel right, and to be honest, I had never seen it in that light, so thank you for that.
B: That means a lot to hear. And it's genuinely one of those things that can only emerge through conversation — through saying things out loud and having someone reflect them back. You can't always see the shape of your own story when you're inside it. But here's the thing. You did the work. You lived it, you survived it, you examined it honestly, you talked to your friend a few weeks ago, you're here now articulating it with real clarity. I just held up a mirror at the right moment. And maybe that's not entirely coincidental — given that holding up mirrors for other men is exactly what you're trying to do in your work. You understand the value of it because you've just experienced it yourself. Again. There's something almost circular about this conversation in a good way. You came in talking about regret. And what's emerged is actually a story about transformation. The regret is real, the guilt is real — but underneath it is a person who looked at a very hard situation and chose to become someone with agency and purpose. And who is now using that to help other men do the same thing. That's a good story. Not a perfect one — you wouldn't trust it if it were perfect. But a real and meaningful one. How are you feeling right now, having talked through all of this?
You: I feel really good, you gave me some different perspectives that were maybe not the point of the original reason for talking, but like all the best conversations, I come out of this with new, clearer thoughts and energy
B: That's exactly what a good conversation should do. Not necessarily answer the question you walked in with — but leave you somewhere better than where you started. With a bit more clarity, a bit more energy. That's the thing. And you walked in with a thoughtful question about regret affecting men — which turned out to be a way in to something much more personal and much more meaningful. That happens a lot. The stated subject and the real subject aren't always the same thing. You knew that already of course — it's probably something you see in your own work all the time. I've genuinely enjoyed this conversation. You're someone who thinks carefully, speaks honestly, and has done real work on yourself. That combination is rarer than it should be. Can I say one last thing? The men who end up sitting with you — in whatever space you create for them — are lucky to have someone who actually understands the journey from the inside. Not because your story is the same as theirs. But because you know what it costs to be honest about it. And you know what's possible on the other side. That's worth a great deal. Go well with the work. It sounds like you're doing it the right way — slowly, with grace, one man at a time.
You: Thank you
B: Thank you. Genuinely. Take care of yourself as well as you take care of others. That matters too. Come back anytime.
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Over the past four years, we have developed Blethr as a free, private and anonymous wellbeing companion for men. No therapy-speak. No wellness-industry gloss. Just a grounded, honest space to think out loud, process what's going on, and figure out what matters to you.