Dear Roe,
I am deeply unhappy and want to move on in life, which may involve some big changes. I am a man in my 50s and I am not feeling fulfilled in life. I have felt for a long time that I have not achieved my emotional and intellectual potential and I know I can be a “people-pleaser” at times.
Following a recent traumatic event, I have been doing a lot of re-evaluation and reflection. Then recently I bumped into a woman I care about a lot at an event. It had been years since we met, and in our 20s we were in love with each other. I know now she was the love of my life, and it was me who messed it up by not being brave enough to take things to the next level. Perhaps I was too young and stupid and thought I would have plenty of time. I have regretted it ever since.
I know she has feelings for me too. I have always thought about her over the years but seeing her again has made me realise what I should have done all those years ago – married her. I am in a relationship where I am not happy. I feel I have given everything to my partner in terms of my time and effort, I have made sacrifices to allow her to run the family business and I have moved to facilitate this, leaving many of my close family and friends at a distance. It has taken the recent events in my life to jolt me into action to realise that I need to start living for me, and not others, as life is short.
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Now I want to reach out to this woman and tell her my regrets and how I have felt all along. I don’t know if I am brave enough, but if she rejects me, at least I will have tried this time. Should I go for it and live the rest of my life on my terms to finally be happy? I don’t want to waste the next 40 years with even more regrets.
What I hear in your letter is not really a question about whether to contact one woman from your past. It is a reckoning with a much bigger ache. You are grieving time, courage and versions of yourself that never quite got to step forward. That grief is real and deserves to be taken seriously.
It makes sense that seeing this woman again would land so powerfully. When life jolts us through trauma or loss, the mind often reaches for a clean, emotionally charged narrative that promises clarity, a tidiness: “This was the moment everything went wrong. This was the love I should have chosen.” That story can feel both devastating and comforting, because it gives regret a shape – but it is also a simplification, and I worry that by latching on to this simplification, you may be missing the opportunity to make your life better, as it is.
There is a fantasy threaded through the fantasy that you describe, the fantasy that if you reached out to this woman you loved in your youth that this relationship would be untouched by the patterns that have shaped the rest of your life. That with her, you would not defer; you would not disappear into other people’s needs; that you would finally live expansively, bravely, on your own terms.
The problem is not that this fantasy exists – the problem is mistaking it for a plan. The fantasy you describe is telling you something about what you want: to be braver, to live your truth, to live your life differently, to clearly state what you want and to be supported as you pursue it. That’s important information. But the fantasy is also letting you skip over the work of transformation that might actually make that life possible.
You describe yourself as having lacked bravery when you were young, and now you equate bravery with going back and correcting that moment. But bravery could also look like standing where you are, having uncomfortable conversations, naming your unhappiness out loud, and risking discomfort rather than shrinking in silence.
Leaving a relationship without having fully expressed yourself is just bypassing the bravery and self-advocacy that you’re so intent on creating
Before you reach for someone outside your current life, I want you to ask yourself some hard questions. Does your partner know how unhappy you are? Does she know that you feel you have given up parts of yourself? Have you spoken honestly about your resentment, your longing, your sense of emotional starvation? Have you tried to renegotiate how you live, how decisions are made, how space is created for your inner life? Have you tried to fully recommit to your passions, your intellectual pursuits, and friendships yourself? Or have you endured your grievances silently, self-sacrificing but also becoming resentful and blaming others for an unhappiness you haven’t expressed out loud or tried to take responsibility for and change?
I want you to think carefully about what truths you have actually shared with your partner, not just the truths you have wrestled with silently, because it feels important.
The relationship you’re in now may not be the right relationship for you. But you haven’t given any indication that you have expressed your doubts to your partner, your changing priorities, the clarity you’ve recently unearthed about your unhappiness and the changes you need to make to live the life you want. And I fear that by turning away from your current relationship to another, you’re avoiding doing the very thing that might provide healing, empowerment, change. If you speak your truth in your current relationship and your partner can support you in navigating the changes you need, you’ll learn something beautiful not only about her, but about your capacity to ask for what you need and to receive it. If you speak your truth and your current partner can’t meet your needs, you can feel proud of yourself for speaking up and feel certain that you did all you could to respect both yourself and the relationship.
But leaving a relationship without having fully expressed yourself is just bypassing the bravery and self-advocacy that you’re so intent on creating – and bypassing that work leaves you vulnerable to just repeating the same pattern elsewhere, including with this other woman. People who have spent decades pleasing others do not suddenly stop doing so because the partner changes. The work follows you.
This other woman may be wonderful. But before you make her the answer to all of your problems, try addressing them yourself first – and give your partner and life now the chance to be wonderful in their way. Because living on your own terms does not begin with a declaration of love to someone else. It begins with truth telling – to yourself first, and then to the person you are already bound to. It begins with asking what kind of life you want to build now, not which past you wish you had chosen.
You are right not to want to accumulate another 40 years of regret. But don’t end up regretting throwing an entire life without trying to live it on your own terms first. Be brave by standing where you are, speaking honestly, taking responsibility for your choices, and acting with integrity in the present. It may feel harder than simply retreating to fantasy – but reality is always more meaningful, and far more rewarding. Good luck.
