The cost of expressing how you really feel

Can I borrow a feeling?

Two Saturdays ago, I was at a house party.

Halfway through the night, I spotted a close friend who I hadn't spoken to in a while.

Call it cosmic timing, given the theme of last week's newsletter or the medicinal courage of a third vodka soda, but I pulled him aside and said:

“I know this is me being crazy, but I feel like we’re drifting.”

He looked surprised. Said he'd been swamped at work. Not online as much. Feeling a bit burnt out.

We smiled. Changed the subject. Talked about something safer like, “When exactly was Harrison Ford at his hottest?”

But the thing I meant to say never really landed.

The connection I hoped to re-establish stayed just out of reach.

In Bronnie Ware's Top Five Regrets of the Dying, Regret #3 is:

"I wish I had the courage to express my feelings"

It's strange, isn't it? That this is a regret people name only when time is almost out. But in many ways, it's not surprising.

We learn early how to hide what we feel.

Babies quickly discover that smiles earn positive attention while tears are met with soothing, distraction, or bitchy looks from the gays trying to enjoy brunch.

So we start performing. We smile when we want to cry. We edit ourselves for the comfort of others.

By the time we hit school, boys in particular, are taught to "be strong" — which usually means "be quiet." Studies show that boys as young as six begin to suppress sadness and fear to meet the masculine ideal.

Emotional management for boys

For some of us, layering in a queer identity adds another mask. You learn to stay charming, but not confronting. Confident, but not too open. Accepted, as long as you stay in the bounds of what's acceptable.

I've been advised more than once — in very polite, professional language — to manage my emotions if I wanted to be taken seriously in straight, male-dominated boardrooms.

Years of journalling, therapy and Huberman Lab podcasts have helped me start unpicking that conditioning. But I'm still working on it. Clearly.

That night, in the Uber ride home, I replayed the conversation. The sentence I'd said — "I know this is me being crazy…" — was a built-in escape hatch. A way to back out if it didn't land well.

Kim Scott, author of Radical Candor, would call it ruinous empathy — caring enough to feel discomfort, but not enough to speak with clarity.

I tried to express a feeling while also discrediting it.

So, when I got home, I wrote the message I should have said the first time.

Lovely to see you tonight. I’ve missed you.
I’ve been wondering if we’re okay.
Are you free for dinner one night this week? I’m around Tues, Wed & Thurs.

No disclaimers. No self-editing. Just the truth. (Plus a few drunken typos, which I’ve edited out in this re-telling.)

Nine minutes later, he replied:

Great to see you too. Let’s do Wednesday.

Over dinner, I caught myself again and again wanting to say, "This might sound stupid…" "Sorry if this is too much…"

But each time, I cut it. And the conversation felt more real for it.

Here's what I'm learning:

• If you care, say so.

• If it hurts, name the hurt.

• If you need something, ask for it.

And do it while you still have time.

Bronnie Ware's hospice patients wished for the courage to express their feelings. The cost, it seems, is a single moment of risk.

Crazy isn't feeling too much. Crazy is letting the feeling die unheard.

If someone's been on your mind lately, try one honest message. No disclaimers.

I don't know if every relationship can be pulled back by a single text. But one of mine was. And right now, maybe that's enough proof.