Why I’m still alone at 37

I started over at 35. I’m happy for the first time in my adult life. But I still can’t find the right person. Why?

This week, I lost someone I care about very much. He didn’t die, but breakups have a way of feeling like a death; you have an idea of yourself with that person, and the future you held so gently in your heart is suddenly gone.

I could rail about how unfair the situation was, how much I gave, how I didn’t get what I deserved at all. It doesn’t matter, though. Life isn’t fair, and anger and self-righteousness don’t help. The fact remains: I lost my partner, the man I loved. Someone I thought I had a future with.

But there’s this: Losing something we value deeply presents us with the opportunity to confront our ego. And it offers a chance to share those insights with others who might be struggling, too.

Over the past 72 hours I have looked closely at my own behaviour in relationships — the kind of painful examination where you turn over in your mind what kind of person and partner you are. Of course, I have faults — we all do — but I came away with precious little to beat myself up over. The person I’m hardest on is typically myself; I am much more forgiving of others faults than my own.

So what’s holding me back? Why does each relationship end in failure? Why am I 37 and alone?

It occurs to me that regardless of how much I have improved my self esteem and my own happiness, I am somehow still picking the wrong people. And this is negatively affecting my ability to create a positive reality for myself.

I don’t mean that I am necessarily picking bad people; I mean that I am choosing partners whose needs and wants aren’t aligned with mine. The bulk of this decision-making happens in the early stages of a relationship, in what I’ll call the “assessment phase.” It’s common, in this stage, for our judgment to be clouded by attraction and ego; I find I don’t apply the same decision-making skills that I would typically employ in less emotionally-loaded situations.

This assessment phase is where I strike out, again and again. It sounds so simple and so obvious, but I consistently fail to proactively seek information that would help me make better decisions. The most basic information being, “What do you want out of this relationship” and, further along, “What do you value about me?”

Naturally, some people can and do misrepresent themselves and their intentions, but consider that I’m not even asking the questions. I’m not looking for the information. I’m not proceeding analytically. When I like someone, I blindly barrel forward.


Part of it is social conditioning: the Disney idea of romance, being swept off one’s feet, legions of bad dating advice and misinformed attitudes about power dynamics in heterosexual relationships. Women are cautioned to hold back for fear of appearing needy, insecure, or overly eager for a relationship (heaven forbid). We’re instructed to let the man call the shots, to play hard to get.

There’s a whole other piece here about why “hard to get” is a misogynist construct, but suffice it to say: you are within your rights to seek information that will help you determine if your needs in a relationship will be met. Questions — provided they are reasonable and respectfully framed — should not lead to pushback. If they do, these are breakups that would have happened anyway. You’ve saved yourself time and frustration. It makes me incredibly sad when women feel they can’t communicate their needs to romantic partners without paying some price. It’s one more way women’s needs (and emotional health, in general) are shut down and erased.

Of course, it makes little sense to barrel into a situation demanding to know how a person feels about you after only a few dates. It takes time to get to know someone and to know how you feel about them, too. But, you can attempt to understand who they are, what they want from you, by asking questions, listening, and observing their behaviour carefully. And you can remain in this assessment mode — in a spirit of observation and fact-finding — until you know the answers, rather than falling into a relationship before you have the information to make the right decision.

The mindset is what’s important, here. It’s not getting swept off your feet. It’s staying firmly in your decision-making zone.

What else holds me back from choosing the right men? The other component is fear of failure. When I’m falling for someone, I desperately want it to work. I want to believe they love me for the reasons I want to be loved. I hear what I want to hear, and believe the patently unbelievable. And yet, I think most of us possess the ability to discern when we’re being manipulated or used — we’d just rather not face it. We possess intuition but we do not use it. We want the story we have told ourselves, the one with the happy ending.

For me, this extends to normalizing problematic behaviour as the narrative begins to unravel. With my ex, I refused to acknowledge glaring red flags that we were not aligned, that what he was seeking in the relationship was not what I wanted. Signs that you are normalizing include making excuses for negative behaviour, justifying, and projecting an unrealistic image of the relationship to your friends and family, while omitting unhappy details. In essence, ‘hear no evil, speak no evil, see no evil.’

By the end of this last relationship, I began to actually feel that he hated me, resented me deeply for some reason I could not identify. His words said one thing — he loved me, he wanted to to make it work — but his actions revealed something else. I was watching it fall apart before my eyes, seeing his behaviour manifest in my reality, but I could not acknowledge what was happening. It was as if I was viewing myself from behind glass. I responded by trying harder to have the loving partnership I’d envisioned, and felt hurt and abandoned when it was clear that he would or could not reciprocate.

Of course, there were gendered aspects to this all — ways that I felt the situation was unfair to me, in a way that women are often taken advantage of. Do I think he meant to treat me this way? Definitely not. Am I justified to feel hurt and angry? Yes, though I refuse to make anger my dominant narrative. I struggle to find a compassionate stance in all of this.

The question isn’t whether people who have hurt us are deserving of forgiveness. The question is what can be gained through hardness of heart.

Whenever I feel I’ve been wronged, there’s an urge to reduce myself to that denominator. To divide by the hand I’ve been dealt. Yes, I’ve picked the wrong partners, but I’m not to blame for their behaviour, either: I have reason to be legitimately disappointed with the garbage that men — even the ‘good’ ones — dish out. And that part isn’t on me.

We give up our power when we fail to maintain our own standards — our ideas of who we are and want to be — in the face of unpleasant realities. I found this out when I left a relationship, a job, and a life that was making me profoundly unhappy (I wrote about this in a post that went viral-ish, called Starting Over at 35). I knew it wouldn’t be easy. I knew I wasn’t going to get the life I wanted overnight.

It took a year to come back to myself, to find my own heart again. It took another six months to take those first wobbly steps toward another person. I was incredibly fragile. But I did it.

My task, now, is to minimize the negativity that comes into my life by learning to choose the people and things that align with my desires. Whether or not I encounter them when or how I’d like, regardless of the sometimes shitty math of being a woman, I have agency. We all do. It is the single most powerful aspect of our humanity. We have the power to create a positive reality within our own hearts and minds.


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