Should You Leave a Boyfriend Who Isn’t Ready to Get Married?

Life lessons from a woman who stayed…and never became a wife

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When you are single and childless in middle age, you become something no one ever wants to be. Not just a cautionary tale, but the person people come to when they are trying to decide what to do about their indecisive boyfriends. Because if anyone would know what to do, it’s the women who’ve already been through all that.

I love my boyfriend, many women have lamented to me. I don’t want to leave him. But he keeps saying he’s not ready for marriage. Should I leave?

Should I leave? I know that question so well, it breaks my heart. It’s a question I asked myself dozens of times over the seven years I was with my indecisive boyfriend. It’s a question I answered with a yes many, many times, and somehow still found my way back into that relationship, back in the pain of his inability to take our relationship seriously or even define what he wanted from it.

So maybe it makes sense that so many have asked me the same question about their own experience. They know that what happened to me could easily happen to them — and that’s their worst nightmare.

But most people expect a simple yes or no in answer to this question. Like everything in life, we prefer a simple solution, an answer that proves there are only two choices: a right one and a wrong one.

I’ve learned a lot about life, love, and myself in the ten years since my relationship ended without ever making it down the aisle. And one of the most important lessons I’ve learned is that this is not a simple question and it doesn’t have a simple answer.

Not all relationships are the same. And not all relationships in a holding pattern will follow the same path.

For instance, there were a lot of circumstances at play in my relationship that kept me committed (for good or bad) and those circumstances will not be present in every relationship, nor will the presence of those circumstances necessarily play out in the same way.

My boyfriend was younger than I am, and because of that, I felt it wouldn’t be fair for me to rush him into such big commitments as marriage and parenthood.

Further, I had not yet done a deep dive into past trauma with the help of a therapist, and had not yet come to understand the ways abusive dynamics in relationships felt comfortable and familiar to me. Hell, I didn’t even know how to identify abusive dynamics in the first place.

I forgave my boyfriend for the first affair he had, without a second thought. I endured his moodiness, his coercive behavior, and the ways he constantly chipped away at my self-esteem.

None of that made me see him for who he really was until he ended our relationship in order to be with a 20-year-old he had been dating behind my back for months — and in the process, called me names, declared he had never loved or liked me, and tried to shirk every financial responsibility he had, claiming I deserved to take on all costs and penalty fees of our breakup because I apparently had wasted seven years of his life when he could’ve been happier with someone else.

So you see, my situation is — I hope — rather unusual. Rather extreme. I’m not sure the average indecisive boyfriend has two personalities, as mine did.

And because of who he was, it wouldn’t have mattered what I did or did not do. I understand now that it was always going to end in a way that was very different than what I had dreamed of.

While it’s important to know what we want in a relationship, I think it’s also important to know why we want it.

In my thirties, when I was with my indecisive boyfriend, I knew I wanted to get married. At the time, I felt that my desire to marry was solely because I wanted to have children, and I felt that a marriage was the safest way to create a family.

Today, when I look back at that time, I know now that I was also feeling an enormous amount of social pressure to get married. People frequently asked me when I was going to walk down the aisle or commented that it seemed odd that I was in my thirties and still didn’t have children. My younger siblings and almost all my friends were married, most of them with children at that time.

I don’t think I was willing to admit it then, but looking back, I know I felt shame at not having yet become a wife or mother by my mid-thirties.

As I’ve gotten older and further into perimenopause with no possibility of pregnancies in my future, the idea of marriage has become less and less appealing to me. I don’t need any legal protections for children I’ll never have, and now that I’m over 45, no one seems to care anymore that I’m not married. I’m a lost cause to society, and thank god for that — who needs the pressure?

I think it’s important for us to know that this might happen. Marriage might become less of a priority as we age. In fact, it might become something we actively don’t want — something that would not only fail to improve our circumstances but actively diminish our quality of life.

And again, it’s important to know why we want to get married in the first place. Is it an actual dealbreaker? Is it something you could live without?

Remember, though, there’s no wrong answer to these questions. Many times, we ask them with the expectation that we should challenge our needs and wants, that we should lean more into compromise.

But I think we should try leaning both ways and find out which feels right. After all, marriage was designed for the benefit of men, and has functioned that way for centuries, flourishing even in the absence of compromise on the male partner’s end. I think it’s entirely reasonable at this stage of the game for women to expect more and compromise less.

Maybe there is absolutely no logical reason why you want to get married. Maybe the cons of getting married actually outweigh the pros in your particular circumstances. But perhaps you want to get married anyways, just because it feels right. Just because you want the symbolism, the ceremony, the moment both of you have to fully opt in both legally and spiritually.

And that’s absolutely a good enough reason to question whether or not to leave a man who’s on the fence about it all.

One question I’ve often been asked is “Why did you stay with someone who didn’t want to get married?” And I always find it odd that anyone would assume that — because why would I?

The problem in this scenario is that, once again, it’s not quite so simple. I specifically chose to stay with my boyfriend because he insisted he did want to get married. He talked about it frequently. He said having a traditional family was part of his vision for his future.

And not only that, but he was literally the only man I ever dated at that point who wanted to get married and have children, at all. I thought I had won the lottery.

At that age (my early thirties), I never would have gotten serious with a man who said he didn’t want to get married.

So what was the problem? He began demonstrating commitment issues about seven months into our relationship. I wisely ended things because I knew what I wanted and figured we were just at different places in our lives.

But he came back after several months and begged me to take another go at it. He said he had grown up a lot in the past few months, that he now felt ready to move forward, that I was the one for him. He didn’t want to get married right away, he said, but soon.

So we got back together. And unsurprisingly the same thing played out. The next time he came back begging for another go, moving in together was suddenly on the table. This time his actions seemed to align with his words. He dove headfirst into the search for our home.

Once we had moved in together, however, everything changed. Over the course of the following six months, he became increasingly disengaged from our relationship. Months later, when I asked him why he hadn’t proposed yet, he dropped a bomb on me: He said my parents’ recent divorce had shaken him up and made him question if he was ready for marriage, after all. He needed more time, he said.

By then, I felt trapped. I’d invested so much into our relationship. Our finances were almost as intertwined as a married couple. And I’d started thinking of him as my forever partner.

I suspect that’s why a lot of women struggle with the Should I leave him? question. The more you invest in your relationship, the harder it is to leave. This is the sunk cost fallacy at work.

And even in the best of situations, this is where I think we get lost.

Here’s the problem with the question Should I leave? We’re asking it from the perspective of the future. We’re asking from the perspective of the opportunity cost.

The underlying narrative of this question is that we’ve chosen one of many options, which now limits the possibility of potential gain (especially in the area of marriage when it comes to an indecisive boyfriend). What we’re really asking is: Would I have a better chance at getting what I want if I choose something (someone) else?

That’s the flaw in the system. That’s why our approach to this issue often doesn’t work out.

If we ask ourselves that question, we must ask it from the vantage point of the present. Not Should I leave so I can find something that fits my needs and wants more?, but Should I leave because this relationship is less beneficial to me than just being on my own?

It might surprise many to hear that I don’t regret that all my many attempts to extricate myself from my past relationship failed. That I stayed for so long. After all, it became clearer and clearer over the years that my boyfriend’s words did not match his actions and there was no reason to believe they ever would. And that’s not even to mention how hard I worked to meet his stated expectations for a perfect wife, even though he kept moving that goalpost.

But when I debated whether I should stay or go, it was always from the perspective of whether or not I’d be able to meet another partner and have the family I wanted. And I see now that that approach would never have worked. I truly believe I’d have ended up in exactly the same place I’m in now if I had followed through with any of the decisions I made to leave.

At the time, what I lacked was the ability to simply choose myself. To even be able to discern whether or not I’d be better off on my own than I was in that relationship. I just couldn’t see it then and I believe I never would have if I hadn’t had this experience.

It’s not about love. It’s not about money. It’s not about our biological clocks.

It’s really not about anything that we think it’s about.

I think it’s about acknowledging hard truths, first of all. Like the fact that men are never indecisive about things that matter to them. And living with someone you aren’t married to but want to be can be as financially and even emotionally damaging as living with someone you are married to but don’t want to be.

Further, it’s about us. It’s about knowing what choosing ourselves looks like — and sometimes that does mean staying. It’s about taking a chance on ourselves in the present moment even without the promise of our dreams being fulfilled in the future — which again, sometimes might mean staying.

So yes, if I knew then what I know now, I would have absolutely committed to our first breakup, the one I initiated when I discovered he wasn’t ready to get serious.

Or at the very least, I would have stood firm in any of the other many breakups I initiated over the years. Not because I wanted to find someone to marry or have children with — but just because I would have been so much happier on my own than with an apathetic, controlling, immature boyfriend.

But I didn’t know until I lived it.

Because of that, I’ve never felt comfortable answering this question when other women ask me if they should leave. It’s really not for me to say. We are all unique, and our relationships are, too.

I can’t help but wonder, though, if there’s even more subtext to that question than what I’ve suggested here. Would we even ask it if we felt happy and fulfilled in the first place?

Maybe there is something simple about this after all.

© Y.L. Wolfe 2025

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Y.L. Wolfe is a writer and artist on a quest to wholeness in the transformative fires of middle age. You can find more of her work at ylwolfe.com. Love her writing? Leave a tip at Ko-fi.

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