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Reaching someone from your past, done carefully.
Plain, careful writing on reaching someone from your past: what to say, when to stop, and how to make the first word safe for both of you.
Getting ready
How to reach out to someone after years of silence, without it being weird
You have thought about it for years. The message itself takes two minutes. The gap between those two facts is the real problem, and it can be closed.
5 min read · September 6, 2026
Is it too late to reach out to someone? The honest answer
Time does not close doors on its own. Reasons do. Here is how to tell whether yours is still open.
4 min read · September 6, 2026
Exes
Should I text my ex after 5 years? An honest answer
The question looks like a yes or no. It is really three questions about you, and only you can answer them.
4 min read · September 6, 2026
Do exes think about you? An honest answer
Yes, almost certainly, sometimes. That answer will not help you. A different question will.
3 min read · September 6, 2026
How to contact an ex who is married, and whether you should
This one is delicate, and the delicacy is the point. Start with their life as it is now, not with what you feel.
4 min read · September 6, 2026
What happens when you reach out to an ex after years: the real outcomes
You are imagining two endings, the wonderful one and the humiliating one. The real outcomes are three, and none of them is either.
4 min read · September 6, 2026
Reaching out to an ex after 10 years: what to expect and how to do it right
A decade is long enough for both of you to become strangers to the people you were. That is not a reason not to write. It is the reason to write differently.
5 min read · September 6, 2026
What to say
What to say when you reach out to an ex after years, with real examples
The message that works is not the one that says everything. It is the one that is easy to receive. Five examples, each in a different tone, with notes on why they land.
5 min read · September 6, 2026
How to break the silence with someone: the message that actually works
You do not need the perfect message. You need the one that makes replying easy. Four templates for four kinds of silence, and why each works.
4 min read · September 6, 2026
Old friends
Reaching out to an old friend after a long time: what actually works
Nobody broke up. Life just happened. That makes an old friend the easiest person to reach and, somehow, still hard to write to.
4 min read · September 6, 2026
Reconnecting with a childhood friend: why it is easier than you think
You knew each other before either of you had a résumé. That is a kind of intimacy no one else in your life has, and it is still there.
4 min read · September 6, 2026
Reaching out to an old colleague you lost touch with
You spent more waking hours with them than with most of your friends, and then a job change erased them. Here is how to say hello without it sounding like you need something.
4 min read · September 6, 2026