The email you’ve been dreading

Aug 12, 2026 • 2 min read

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Hello, last week I promised you the actual words to write in a reconnection email.

A week ago, we talked about the follow-up you’ve been dreading…

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The warm relationship gone cold.

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The ex-client you keep meaning to email.

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The intro you never chased.

Knowing that helps.

But it doesn’t write the email.

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The blank screen is still blank.

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The cursor still blinks.

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And somehow the words “Hi – it’s been a while” feel impossible to follow.

So today, let’s write the words.

Not a template to paste – those read like templates.

A structure that you can make your own in about four minutes.

There are three ways back into a cold relationship.

Pick the one that fits.

The first: their news.

Something happened on their end…

A promotion.

A raise.

A new role.

A milestone.

An award.

You saw it, and it’s a real reason to reach out that has nothing to do with you wanting something.

“Saw the news about [the round / the role / the move] – genuinely happy for you. It’s been too long. Would love to hear how it’s going when you have a minute.”

No pitch.
No “and while I have you.”
Just a real acknowledgment of their moment.

The work conversation comes later, on its own.

The second: a genuine question.

You don’t have their news, but you have something you’d actually value their view on.

People love being asked – it’s a compliment that costs them nothing to receive.

“Been thinking about [a real thing in their world], and you’re one of the few people whose take I’d trust on it. No agenda – just curious how you’re seeing it. And it’s been too long regardless.”

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The key word is real.

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If the question is a pretext, they’ll feel it.

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That single follow-up is one relationship.

If it’s genuine, you’ll probably get a longer reply than you expected – and a reopened door.

The third: the honest one.

No news.

No clever question.

Just the truth.

Which is disarming precisely because so few people use it.

“You’ve crossed my mind a few times lately and I realized I’d let too much time pass. No reason beyond that – just wanted to say hello and see how you’re doing.”

This one works far better than it has any right to.

The plain admission that you let time pass is the opposite of the polished pitch everyone else sends.

It reads as human.
Because it is.

A few things that sink the reconnection, whichever door you pick:

Don’t apologize for the silence at length.
One light line – “it’s been too long” – and move on.
A paragraph of guilt makes the reader carry your discomfort.

Don’t bundle the ask into the first message.
You reached out to reconnect.
Let that be the whole job.

The moment you attach “and I’d love to explore working together,” it stops being a reconnection and becomes a pitch.

And they can feel the difference instantly.

Don’t over-explain why you went quiet.

The whole thing takes four minutes. Choose the person – the one who came to mind just now – pick the door that fits them, and send it before the blank screen wins another week.

Oh, and one more thing.

I put all three scripts on a single page you can keep – plus a fourth door I didn’t have room for here. It’s the strongest of the four, and the one most founders never think to use: the one that reconnects by giving instead of asking. You arrive carrying something – an introduction, a lead, a name they’d want to know – which makes it impossible to read as self-serving, and almost impossible to ignore. The page has the exact words for it, plus what to do when someone doesn’t reply the first time.

Grab the one-page pdf here →

The research on this is consistent:

People underestimate how much others appreciate hearing from them – most of all when it’s been a long time.

The message you’re most nervous to send is the one they’ll be most glad to get.

All that’s left to do is the sending.

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The email you’ve been dreading

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