I didn’t understand what healthy boundaries in relationships actually looked like until a woman called me out in a Trader Joe’s.
It sounds like the least consequential story imaginable. But it taught me something I hadn’t been able to learn any other way.
I was with the first woman I dated after I stopped drinking. She was everything to me at that point — I’ve written about her before. The relationship eventually broke my heart in ways that took years to work through. But before any of that, there was this ordinary afternoon where she got excited about going to Trader Joe’s and asked if I wanted to come along.
I didn’t want to go. I hadn’t made a list for that store. I didn’t really know what they carried. I probably didn’t have extra money to spend. None of it made sense for me that day.
I said yes anyway.
When we got there and she picked up on the fact that I had zero interest in being there — that I was just physically present while mentally somewhere else — she got upset. She looked at me and said, why didn’t you just tell me?
It was a fair question. And I didn’t have a good answer.
I said yes because I wanted her to be happy. Because I didn’t want to disappoint her. Because somewhere in me I believed that going along with what she wanted — even when it wasn’t what I wanted — was how you kept someone around.
That’s not love. That’s self-abandonment. And I didn’t know the difference yet.
I’ve been reading and re-reading Boundaries by Cloud and Townsend for years now. My brother recommended it as the first book in a two-man book club we started together. I picked it up expecting something practical and got something that fundamentally changed how I understood myself and my boundaries in relationships. This post is what I’ve learned — not from having it figured out, but from living on both sides of it.
1. What Boundaries in Relationships Actually Mean
The word “boundaries” gets misused constantly. People treat it like it means shutting others out, being cold, protecting yourself from connection. That’s not what boundaries in relationships are.
Cloud and Townsend define a boundary as a property line. It defines where you end and someone else begins. It’s not about keeping people away — it’s about being clear on who you are, what you need, and what you’re actually willing to do versus what you’re just agreeing to because you’re afraid of the alternative.
When I said yes to Trader Joe’s, I wasn’t being kind. I was being unclear. I was handing her a version of me that wasn’t real — agreeable, easygoing, no preferences of his own — and then resenting the situation from the inside while she had no idea anything was wrong.
That’s the invisible cost of no boundaries in relationships. The other person doesn’t get the real you. They get the performance. And eventually — in little moments or big ones — the gap between the performance and reality shows up. And it’s confusing for everyone involved.
A boundary isn’t “I don’t want to be around you.” A boundary is “here’s who I actually am.” The people worth keeping in your life will respect that. Some of them will find it more attractive than the version of you that just goes along with everything.
2. Some People Find Your Boundaries in Relationships Sexy — and That Tells You Everything
I was in Alaska when I learned this in the most direct way possible.
I was at a movie with a woman I was seeing up there. At some point she asked me to go get her a drink. I don’t drink — hadn’t in years — and I didn’t feel like getting up. More than that, I didn’t think it was my job to go get it. If she wanted a drink, she could go get one.
So I told her no.
Not harshly. Not coldly. Just — no, I’m good here, if you want one you can grab it.
She paused for a second and said: ohhh. a boundary. sexy. And got up and got her own drink.
I think about that moment more than it probably deserves. Because it flipped something in my understanding of boundaries in relationships. I had spent so much of my life treating my own preferences like inconveniences — things to hide or override so the other person would stay comfortable and keep liking me. And here was someone responding to a simple, honest no with genuine attraction.
The right people don’t leave because you have boundaries. They lean in.
The wrong people — the ones who need you to have no edges, no preferences, no pushback — those people were never going to work out anyway. Your boundaries in relationships are a filter. They show you early who you’re actually dealing with.
3. The Boundary You Don’t Set Is the One That Costs You the Most
This one is harder to write.
There was a woman in Savannah. I’ve thought about her more times than I can count. Looking back, she was exactly what I should have wanted — the kind of person who wanted to be there, who wanted to build something real. I wasn’t ready for what she was offering. And a big part of why I wasn’t ready came down to a boundary I failed to hold — not with her, but with myself.
I didn’t have a boundary around my own thinking. Around where I was letting my attention go, what I was entertaining internally, what I was prioritizing over what was actually in front of me. And that cost me the relationship. It cost me her. And it hurt then, and if I’m honest, it still does.
Cloud and Townsend write that boundaries in relationships aren’t just about what we say to other people — they’re about what we allow inside ourselves. The thoughts we entertain. The patterns we feed. The decisions we make before anyone else is even in the room.
I wasn’t grown enough for that relationship. I know that now. And the painful part isn’t that I lost her — it’s that I can see exactly what I would have needed to do differently and I didn’t do it. That’s a specific kind of regret that doesn’t go away fast.
I’m not sharing that to sit in it. I’m sharing it because if you have a relationship in your rearview mirror that you know you lost because of your own unresolved stuff — you’re not alone in that. And the only thing to do with it is learn from it and become someone different going forward. That’s the whole work.
4. When Someone Pulls Away — How Boundaries in Relationships Change Your Response
For most of my life, when I felt someone pulling away, I pushed harder. More texts. More effort. More trying to fix whatever I thought was broken. More performing the version of myself I thought they wanted.
It never worked. It made things worse. Because what I was really communicating with all that effort was: I don’t trust that I’m enough on my own, so I’m going to try to earn my way back in. And people can feel that energy. It’s not attractive. It’s desperate. And desperation confirms whatever doubt was already there.
I’ve done enough reading and enough real-life repetition to understand now what that pattern was rooted in. Abandonment fear. The deep, mostly unconscious belief that people leave — and that when they start to, the only option is to hold on tighter.
Boundaries talks about this directly — healthy boundaries in relationships mean understanding what you can and cannot control. You cannot control whether someone stays. You can only control whether you show up as yourself — clearly, honestly, without contorting yourself into whatever shape you think they need.
Now when someone pulls away, I might push once — I’m human, and I’m still working on this. But then I let it go. I sit with whatever that brings up — the wondering, the questioning, the old familiar spiral — and then I move forward. Because if someone is pulling away from the real me, holding on tighter doesn’t fix that. It just delays the inevitable while costing me my dignity in the process.
You can’t chase someone into choosing you. And you don’t want to.
5. The Most Important Boundary in Any Relationship Is the One With Yourself
Everything in this post points back to the same place.
The boundaries we struggle to set with other people are usually a reflection of the boundaries we haven’t set with ourselves. The inability to say no to Trader Joe’s wasn’t really about her — it was about me not knowing what I actually wanted, or not trusting that what I wanted was worth saying out loud.
Cloud and Townsend write that we are responsible for ourselves — our choices, our feelings, our responses. Not for managing other people’s emotions or keeping everyone comfortable at the expense of our own clarity.
That’s still a daily practice for me. I don’t have boundaries in relationships mastered. I still catch myself agreeing to things I don’t want, still feel the pull to perform the version of myself I think someone needs, still have moments where the abandonment fear shows up louder than the boundaries I’ve built.
But I’m more aware of it now than I’ve ever been. And awareness is where it starts.
You’re allowed to have preferences. You’re allowed to say no. You’re allowed to be someone with edges — someone whose yes actually means something because your no is real.
That’s not coldness. That’s self-respect.
And self-respect, it turns out, is one of the most attractive things you can bring into any relationship.
I’m still learning that. Still building it.
Still climbing.
Built on the Climb.
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