Oct 23, 2026 · 6 min · 3 segments
*"Every time someone checks in on me since my divorce, I feel guilty for needing it. I keep saying 'I'm fine' even when I'm sitting on my kitchen floor crying five minutes earlier."* In this Hey…
This week's letter is one that I think a lot of you will recognize yourself in immediately.
It's that specific guilt of needing support and reflexively saying that you're fine instead.
Hey Olivia, every time someone checks in on me since my divorce, I feel so guilty for needing the support.
My sister texts most mornings just to say she's thinking of me, and every time, my first instinct is to make her stop worrying, not to actually answer honestly.
I keep saying I'm fine even when I'm sitting on my kitchen floor crying, because I don't want to be the friend who's always going through something, the one people brace themselves for before they call.
How do I let people actually show up for me? Oh man, I hear how disorienting this role reversal genuinely feels.
Being the one everyone came to for years, the steady one, the one with the answers, and then suddenly needing that same kind of support yourself, that is not a small adjustment to make, my friend.
It makes complete sense that some part of you doesn't quite know how to be on this particular side of it yet, even though you're clearly aware something needs to shift.
I'm fine isn't dishonesty in any real moral sense, and I don't want you carrying guilt about that phrase like it's a lie that you're telling.
It's protection, protection of your sister from worry, protection of yourself from feeling like a burden to the people you love.
Both of those impulses genuinely make sense given everything that you've described, but they're also quietly blocking the exact connection you're actually asking me how to find.
Here's the real cost of saying, I'm fine, every single time someone checks in.
If you consistently say you're okay, even the people who love you the most deeply will eventually believe you, and they'll step back.
Not because they stopped caring about you, but because you told them repeatedly that there was nothing left to stay close to.
Letting people actually show up for you doesn't mean giving every detail every time someone asks how you are.
There's real room between I'm fine and telling someone the entire story from start to finish.
This week's letter is one that I think a lot of you will recognize yourself in immediately.
It's that specific guilt of needing support and reflexively saying that you're fine instead.
Hey Olivia, every time someone checks in on me since my divorce, I feel so guilty for needing the support.
My sister texts most mornings just to say she's thinking of me, and every time, my first instinct is to make her stop worrying, not to actually answer honestly.
I keep saying I'm fine even when I'm sitting on my kitchen floor crying, because I don't want to be the friend who's always going through something, the one people brace themselves for before they call.
How do I let people actually show up for me? Oh man, I hear how disorienting this role reversal genuinely feels.
Being the one everyone came to for years, the steady one, the one with the answers, and then suddenly needing that same kind of support yourself, that is not a small adjustment to make, my friend.
It makes complete sense that some part of you doesn't quite know how to be on this particular side of it yet, even though you're clearly aware something needs to shift.
I'm fine isn't dishonesty in any real moral sense, and I don't want you carrying guilt about that phrase like it's a lie that you're telling.
It's protection, protection of your sister from worry, protection of yourself from feeling like a burden to the people you love.
Both of those impulses genuinely make sense given everything that you've described, but they're also quietly blocking the exact connection you're actually asking me how to find.
Here's the real cost of saying, I'm fine, every single time someone checks in.
If you consistently say you're okay, even the people who love you the most deeply will eventually believe you, and they'll step back.
Not because they stopped caring about you, but because you told them repeatedly that there was nothing left to stay close to.
Letting people actually show up for you doesn't mean giving every detail every time someone asks how you are.
There's real room between I'm fine and telling someone the entire story from start to finish.
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