Can We Grieve Someone Twice?

By Chess | The Scapegoat Club

When people say, “You’ll regret it when they die,” it sounds like wisdom. But what if it’s really a curse dressed up as compassion?

The Question That Won’t Let Go

If you’ve ever been estranged from a parent or family member, you’ve probably heard this:

“You’ll regret it when they die.”

It’s spoken like a prophecy — as though regret is the inevitable price for protecting ourselves. But I’ve started to wonder: Can we grieve someone twice?

Can we grieve the living and then grieve them again when they’re gone — and if so, what’s actually being mourned the second time?

If you’re new here, I’m Chess — a therapist, coach, and fellow survivor of the kind of families who were supposed to love us but maybe didn’t know how. This is personal terrain for me.

I’m not talking about something I once lived through. I’m still living it.

So let’s walk through this together.

1. Grieving the Living

I believe we can grieve someone once, twice, maybe many times — but the grief isn’t the same each round.

For many of us, the first grief comes while they’re still alive.

It begins quietly — that dawning realization that the parent you needed isn’t the one you got. That the love you hoped for was always conditional. That home never really felt safe.

“We grieve the fantasy — the version of them we had to believe in just to survive.”

We grieve the parent they refused to be. And we grieve the part of ourselves that kept believing they might change.

💭 If you pause here — who was the version of them you hoped would finally show up? What did you keep believing, long after the evidence said otherwise?

That hope was a survival mechanism. Letting it go can feel like letting go of oxygen. But mourning that fantasy is often the first breath of real freedom.

2. When They Die

If and when they pass away, another wave of grief can arrive — but this time it’s about finality.

There’s no more “maybe someday.” No more apology that might come. No more chance of change.

The last glimmer of hope goes out, and that’s its own heartbreak.

“It’s not always missing them — it’s missing the possibility that they might have become someone different.”

💭 If you imagine that day, what do you think you’d feel first — sadness, relief, confusion, peace? Maybe all of them at once.

3. Learning to Walk With a Limp

Grief isn’t about getting over it. It’s about integrating the loss — learning to live with the hole instead of trying to fill it.

“We don’t cover it up. We don’t pretend it’s fine. We learn to walk with a limp — and that’s still walking.”

Estrangement grief isn’t about what we had. It’s about what we hoped for. The dad who might have listened. The mom who might have stopped criticizing. The sibling who might have shown kindness.

We don’t grieve the people they were. We grieve who they couldn’t or wouldn’t become.

💭 If you could name what you most hoped for, what would it be? A kind word? Accountability? One moment of safety?

4. Relief and the End of the Threat

For some, death brings sadness. For others, relief. Because the threat is finally gone.

I don’t mean we wish them harm — only that we’ve spent years begging them to stop, reasoning, pleading, explaining — and they never did.

Sometimes, the only peace left comes when the danger ends, even if it ends in death.

“If you feel both sadness and relief, it doesn’t make you cruel. It makes you human.”

And sometimes, the grief isn’t even for the person — it’s for the explosion they leave behind. If they were the ringleader, what happens now? Will the others scatter, stay silent, or take the throne?

Feeling sadness and relief is natural when we are grieving a difficult relationship.

5. “You’ll Regret It When They Die”

People love to say this — as if regret is guaranteed. But in truth, what most people feel isn’t regret. It’s sadness that love was never safe, that we had to become our own parents just to breathe.

“Regret is often a stick people use to beat us back into contact. It’s not a prophecy — it’s a pressure tactic.”

💭 If you had to choose between a possible future grief and a known present harm — which one could you live with? Which one would destroy you?

We’ve already survived the unthinkable. And we know the alternative: staying in relationships that break us again and again. So when people try to scare us with future pain, we can remember — we already know what that pain feels like.

6. Signs You’re Healing

There’s no finish line to grief, but there are small signs — quiet shifts that tell us something’s changing.

You might notice you’re not waiting for their apology anymore. You stop replaying the arguments in your head. You can remember them without shrinking into shame. You can feel sadness without being undone by it.

That’s not weakness. That’s growth.

💭 What’s one small sign that your grief is softening — even slightly? Can you name it and give it credit?

“Grief doesn’t mean we’re broken. It means we’re telling the truth — about what was never going to be, and our choice to keep living anyway.”

7. The Courage to See Clearly

Yes, I believe we can grieve someone twice — or more. But each layer reveals a new truth.

Grieving doesn’t mean we were wrong to walk away. It means we were brave enough to see clearly, even when the truth hurt like hell.

And if relief comes when they’re gone, that doesn’t make you cold-hearted. It means your body finally believes it’s safe.

If this stirred something up in you, please know you’re not alone.

You’ve already survived so much. Grief doesn’t erase that — it proves it.

Take care of your heart,

Chess xx