Reconnecting with someone you have not spoken to in years

The thing you are worried about is not what they think

You are imagining that they will notice the gap and read the timing. In practice most people are pleased to hear from someone they liked working with, do not track the interval, and assume nothing about your motives unless the message tells them to.

What does read badly is a first message in years that consists entirely of a request. Not because asking is wrong, but because it says the relationship was storage.

A sequence that works

• Reopen with something specific you remember — a project, a decision, something they did that you have since used. Specific beats warm.
• Say what you are doing now, in two lines. They are curious and it saves them asking.
• Ask about them, and mean it. This is where the relationship actually restarts.
• Leave the ask for later — or, if the timing genuinely forces it, name the awkwardness plainly and briefly. Executives respect directness more than choreography.

A first message in three years that is only a request tells the other person what the relationship was for.

When you do have to ask straight away

Sometimes something is happening now and there is no time to rebuild slowly. Say so: that you are conscious it has been a while, that something specific has come up, and that you would rather ask honestly than manufacture a reason to be in touch. Most people find that more respectful than the alternative, because it is.

Who to reopen first

The honest limit

Some relationships have genuinely lapsed, and a warm message will not revive them. That is fine — the exercise is not to reanimate everyone, it is to find the ten that are still live and worth an hour each.