6 Lessons I Learned Sitting Across from an Estranged Mom
- Chess
- Sep 27
- 3 min read
What happens when you sit across from a stranger and play the role of the child who cut them off?
That’s the experiment I joined when I was invited onto a podcast: me bringing the child’s perspective, and a woman named “JC” bringing the parent’s. The idea was that if we talked openly, maybe something would shift—for her, for me, or for anyone listening.
When the episode was finally released, I listened back for the first time. And what I noticed wasn’t just the conversation itself, but what it revealed about estrangement and what it really takes to move forward. Here are six lessons I took away.
1. Pain Is Real on Both Sides—but Unevenly Shared
JC spoke often about her unbearable pain. And I don’t doubt her. Estrangement can feel like grief without a funeral.
But here’s what I kept thinking: where is the space for the child’s pain? For the child who begged for love and was met with rejection, punishment, or silence. For the child who considered ending their life, only to be called “selfish.”
Estranged children know excruciating pain too—usually long before the cutoff.
2. Silence Can Sound Like Defensiveness
JC was gracious at times, open to feedback, even sincere about wanting real connections. But she was also vague, resistant to being seen, careful with details.
Is that self-protection? Or unwillingness to be fully honest? I still don’t know. But I do know this: when defensiveness shows up, healing stalls. It left the conversation feeling like a loose end.
3. Empathy Without Boundaries Is Just Old Conditioning
Listening back, I realized how much I tried to rescue JC. I wanted to soothe her. I even came close to contradicting her children—a moment I regret.
That’s my old training: people-pleasing, smoothing discomfort, keeping others calm. The lesson? Empathy has to be paired with self-protection. Otherwise, it’s just self-abandonment dressed up as care.
4. Sometimes You Won’t Get Closure—Only Questions
Was JC narcissistic? Was I naïve to take her at face value? Was I being used?

I can’t answer those questions even now. But maybe the point isn’t to land on a neat conclusion. Maybe the point is learning to hold the questions without betraying myself in the process.
5. Healing Requires Looking Beyond Estrangement
One of the most hopeful things JC said was that she’s learning her world is bigger than her kids who don’t speak to her.
That shift matters. Because estrangement can feel like a black hole that consumes everything.
Healing starts when you widen the lens and build support beyond that single relationship.
6. Reconciliation Isn’t a Reset Button
If reconciliation happens—and it doesn’t always—it cannot be a return to “what was.” That old version of the relationship is gone.
What’s possible is something new. Something built with honesty, boundaries, and vulnerability. Without those, reconciliation is just repetition.
Final Thoughts
Sitting across from an estranged mom left me with more questions than answers. But maybe that’s the point: estrangement isn’t neat. It’s raw, layered, and often unresolved.
If you’re estranged—on either side—please don’t go through this in isolation. Find support that doesn’t just fuel anger, but helps you heal. Therapy, community, and connection matter.
Estrangement is more common than most people realize. Mistakes don’t have to define you forever. And healing, whether together or apart, requires vulnerability, honesty, and courage.
Much love,
C xxx
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