What If We Had Separated? The Question I Still Ask Myself After 29 Years

This content is shared for storytelling, educational, and entertainment purposes only and is not a substitute for professional counseling or therapy.

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I want to start this post by saying something that not a lot of people have the courage to admit out loud: even after almost three decades with the same person, I still sometimes ask myself — did I make the right decision?

I am not saying that because I am unhappy. I am not saying that because I am planning to walk away. I am saying it because I am a human being, a thinker, and a woman who has never stopped being honest with herself — even when that honesty is uncomfortable.

And I think you deserve that same honesty.

Approaching 29 years together, I applaud Kalif and myself. I really do. Because sustaining a relationship for nearly three decades is not easy. It is not a fairytale. It is a daily choice that sometimes feels clear and sometimes feels like the hardest thing you have ever done. Every day is not great. There are seasons of confusion. There are moments I sit with a quiet question that never fully goes away:

What would my life have looked like if we had taken a different path?

This post is for every woman who has ever asked herself that same question — whether you are in year two or year twenty-two. Whether you stayed. Whether you left. Whether you are still standing at the crossroads, unsure which direction to go.

This is not a post about failure. This is a post about honesty, about the weight of real choices, and about why — no matter which path you choose — you are not less than.

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Let Me Be Honest: The ‘What If’ Is Real

I have shared pieces of our story before. I have written about the twenty-five-year mark, the twenty-eight-year mark. I have talked about the trials — including infidelity — and how we moved through them. But what I have not said as plainly as I am about to say it right now is this:

There were moments when separation felt close. Not distant. Not hypothetical. Close. Real enough that I sat with the actual weight of what walking away would mean — not just emotionally, but practically. Logistically. As a mother. As a woman. As an individual who had built an entire life inside of this relationship.

If you have read my post How to Make a Relationship Work Even After a Heartbreak, you know that we went through something significant around years sixteen and seventeen. What I want to add to that story now — from the woman’s seat, from my seat — is what was happening inside of me during that time. The questions I was quietly carrying.

Because the truth is, I did not just ask myself, do I still love him? Love was there. Love was never the question. Love is rarely the question.

The real questions were harder than that.

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The Questions I Actually Asked Myself

I am a practical thinker. A deep thinker. And when I was sitting with the possibility of a different life, I did not get lost in the romance of what starting over might feel like. I got real with myself. The way I always do.

These are the actual questions that crossed my mind:

If I leave, the next person I meet — will they come with their own set of baggage that I now have to accept?

Because here is what people do not tell you when they say leave and find someone better: everyone has a history. Everyone has wounds. Everyone has something they are carrying. You are not trading in a complicated situation for a simple one. You are potentially trading one set of complexities for another. And that truth deserves to sit with you for a moment.

The second question I asked myself:

How will someone new treat my children? Will they see my kids the way they deserve to be seen?

I have never introduced another man to my children. The only person they have ever known in that role is their father. And as a mother, that matters to me deeply. Not just for their stability, but for how they grow up understanding what relationships look like, what they model, what they normalize.

I thought about that. A lot.

The third question:

How much time would I need before I could even enter a new relationship in a healthy state of mind?

Because healing is not a weekend. It is not a few months. When you leave a nearly two-decade relationship — or longer — you do not just pack your bags and walk into the next chapter ready. You carry grief. You carry identity questions. You carry the version of yourself that was built inside that relationship, and you have to figure out who you are outside of it. That takes time. Real time.

And I was honest enough with myself to know that I needed to factor that in. Not just who I might become. But how long the becoming would take.

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Did the Kids Play a Role? Yes. But They Were Not the Only Reason

I want to address this directly because I think a lot of women carry guilt around this — the idea that they stayed in a relationship primarily for their children, and whether that was the right or wrong thing to do.

My children played a role in my decision. I will not pretend otherwise. As a mother, I have always asked myself: how do my kids see me? What are they watching? What relationship template are they being handed?

And one thing I am clear on: my children have only ever known their father as the man in our home. That consistency meant something to me.

But I also want to be clear — they were not the only reason I stayed. Staying purely for the children, without any personal conviction, without love, without a genuine belief that the relationship could be rebuilt, is its own kind of slow damage. Children do not just need two parents under one roof. They need to see two people who are choosing each other with intention — or two people who have chosen, with maturity and love, to parent separately.

I stayed because when I stripped everything away — the kids, the house, the years, the history — I still loved this man. I still believed in what we could build. That was my reason. The children reinforced it. They did not create it.

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The Daydream I Am Not Ashamed Of

Here is the part I want every woman to hear, because I think it will give you permission to breathe:

Even now, at forty-three years old, approaching twenty-nine years with the same person, I still sometimes let myself wonder. What would my life have looked like? Who would I have become? Where would I be?

I am a bit of a daydreamer. And in those quiet moments, I do not think there is anything wrong with sitting in the ‘what if.’ It does not mean I love him less. It does not mean I am about to make a move. It does not mean the relationship is in trouble.

It means I am human.

Asking ‘what if’ does not make you disloyal. It makes you honest.

And I believe deeply that the women who are most at peace in their relationships — whether they stayed or left — are the ones who were honest with themselves about what they wanted, what they feared, and what they were choosing. Not the ones who suppressed the question, but the ones who held it, examined it, and then made a conscious decision from that place of clarity.

So if you are somewhere sitting with your own version of ‘what if’ — whether you are three years in or thirty — I want you to know that the question is not the problem. What matters is what you do with it.

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At Forty-Three, Here Is What I Know About Relationships

Now more than ever, it is clear to me that relationships are extraordinarily hard to sustain. I do not say that to discourage you. I say it because I think the cultural narrative around long-term love does not prepare people for the reality of what staying actually requires.

It requires choosing someone on the days you do not like them. It requires doing your own healing work so you are not bleeding on someone who did not cut you. It requires the kind of communication that makes you uncomfortable. It requires forgiveness — not just once, but repeatedly, for different things, over many years.

And some people do all of that and still find themselves at a point where the relationship is no longer serving either person. And that is not failure. That is evolution.

I wrote about this in the companion post to this one — How to Make a Relationship Last: 6 Pillars Every Couple Needs — and one of the things Kalif and I discussed is that people grow. The version of you at twenty-two is not the version of you at forty-three. Sometimes people grow together. Sometimes they grow in different directions. Neither outcome is a moral failing.

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Separation Is Not Failure. Staying Is Not Weakness. Let Me Say That Again.

This is the core of what I need you to take with you today:

Your relationship — or the ending of it — does not define your worth.

If you choose to separate, you are not a failure. You are not less of a woman. You are not someone who gave up. You are someone who was honest enough with yourself to recognize that what you had was no longer working — and brave enough to choose something different.

If you choose to stay and fight for it, you are not weak. You are not in denial. You are not settling. You are someone who looked at what you had, weighed the complexity of it honestly, and chose to rebuild. That takes a different kind of courage.

Both choices are valid. Both choices are real. And neither one makes you more or less than the woman standing next to you who chose differently.

What I will say is this: be judgmental of neither. You do not know the personal battles that two people are fighting inside of a relationship. You do not know what conversations happened behind closed doors, what was tried and failed, what was sacrificed and held. So withhold the verdict. Trust that the people inside that relationship are trying to make the best decisions available to them in that moment.

And if you are someone who has already walked away — if you have navigated a separation or are in the middle of one right now — I want you to visit this post: How to Survive in a Relationship. Because surviving is not just something you do inside of love. Sometimes you have to survive the leaving of it, too. And that takes just as much strength.

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A Letter to the Woman Standing at the Crossroads Right Now

I see you.

You are standing in the middle of a decision that nobody else can make for you. You have probably been here for a while — going back and forth, weighing the love against the pain, the history against the hurt, the hope against the exhaustion. And maybe you have people around you with opinions. Maybe you have people telling you what you should do, what they would do, what you deserve.

But here is what I want to say to you directly:

• You are allowed to take your time with this decision. It does not need to be made in a moment of anger or in a moment of desperation.
• You are allowed to love someone and still choose to leave. Love alone is not always enough. And knowing that does not make you cold — it makes you honest.
• You are allowed to stay, even if others think you should go. This is your life, your relationship, your choice. Not theirs.
• You are allowed to ask ‘what if’ without it meaning you have already decided. The question is not the answer.
• You are allowed to grieve the relationship even if you are still in it. That grief is telling you something. Listen to it.
• You are allowed to put yourself first — not as an act of selfishness, but as an act of survival. A relationship cannot be sustained by one person running on empty.
• You are allowed to change your mind. Staying is not a permanent verdict. Neither is leaving.

Whatever you decide, I want you to decide it from a place of clarity, not fear. From honesty, not pressure. From love for yourself first — and then from whatever love you still have for the other person.

Because a relationship does not define you. Your choice does not define you. What defines you is how well you know yourself — and how willing you are to honor that, even when it is hard.

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Key Takeaways

• Asking ‘what if’ does not make you disloyal or ungrateful — it makes you honest. Honesty is where real decisions come from.
• Love is necessary but not always sufficient. The practical questions — about children, timing, healing, readiness — deserve to be asked alongside the emotional ones.
• Children can be a factor in your decision without being the only factor. Staying purely for the children, without personal conviction, is its own kind of slow damage.
• Separation is not failure. It is a recognition that two people have grown in directions that are no longer compatible. That takes clarity and courage.
• Staying is not weakness. It is a different kind of courage — the kind that chooses to rebuild something real rather than walk away from it.
• You do not have the full story of anyone else’s relationship. Withhold judgment. Trust that people are making the best decisions available to them in that moment.
• A relationship does not define your worth. Whether you stay or go, you are whole. You are enough. You are not less than.
• At forty-three, approaching three decades with the same person, I still ask myself ‘what if’ — and I have made peace with the fact that the question and the commitment can coexist.

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Listen to the Full Conversation

This post is the spin-off companion to the Real Talk Series episode where Kalief and I open up about what it actually takes to make a relationship last. Listen to the full episode on Sherley’s Show and hear both sides of the story — unfiltered.

Sherley’s Show offers three ways to connect with the conversations that matter:

• Real Talk Series — Sherley and her husband get raw and real about marriage, longevity, and the hard truths behind a nearly 30-year relationship.
• Conversations — Sherley and Kira dive deep into infidelity, heartbreak, healing, and what it really means to rebuild after crisis.
• Interviews — Expert guests and everyday women share knowledge, perspective, and lived experience on relationships, self-love, and everything in between.

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Let’s Keep the Conversation Going

Have you ever stood at that crossroads? Have you chosen to stay — or to go — and want to share what that decision felt like from the inside? Drop it in the comments. This is a judgment-free space, and your story might be exactly what another woman needs to read today.

Share this post with someone who is in the middle of that decision right now. Sometimes the most powerful thing we can do for each other is say: I see you, I have been there, and you are going to be okay — no matter what you choose.

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