You saw them every weekday, then never again.
You used to speak almost every day without planning it.
Lunch at the same hour. The same running joke about the printer. A Slack thread that went off topic within four messages.
Then one of you changed jobs, and the conversation ended with the calendar.
You both said you would stay in touch. You meant it at the time.
You are eating lunch alone and you catch yourself thinking, they would have found this ridiculous. Their name has not been on your screen in three years.
With an old friend, you at least know you were friends. With a former coworker, the question underneath is quieter and slightly uncomfortable: were we actually close, or were we only close because a company put us in the same room?
So the hesitation stacks up. Will this look like networking. Is it too late. Do they remember it the way I do. Will they assume I want something.
That hesitation is normal. It usually says more about how much the person mattered than about whether the message is a good idea.
There is a real difference between missing the person, wanting one catch up, wanting a friendship back, wanting advice, and needing a favour.
Mixed motives are not a crime. Most reconnections have more than one reason behind them. The problem starts when the first message hides one of them.
Pick the honest reason and write from that. The rest can wait.
If the first message could have been sent to any useful contact, it probably does not feel personal enough.
One real detail fixes that faster than a paragraph of warmth. The lunch place. The project nobody wanted. Their habit of arriving with two coffees. The thing that actually brought them to mind this week.
Specific beats sincere-sounding. Specific is what makes them realise you remember them, not their job title.
If the first message could have been sent to any useful contact, it is not personal enough yet.
Do not open with a referral request. Do not lead with a career update nobody asked for. Do not write it as casual if you actually need something.
Do not make the old workplace the whole relationship, and do not ask five questions in one message. Do not propose a reunion before you have said hello.
And if it stays quiet, leave it quiet. Repeated follow-ups turn a kind message into pressure.
Answer what they actually said instead of moving to the next question. A reconnection that turns into an interview dies quickly.
Share something small about your own life so they are not the only one being asked. Suggest coffee when the exchange already feels easy, not in message two.
Something like this is usually enough: "It would be nice to catch up properly sometime. No pressure, but I would happily grab a coffee if you are ever nearby."
If you do have a work question, let the conversation restart first. A relationship that has just reopened can carry it a week later. It often cannot carry it on day one.
Silence is rarely a verdict. They are busy, the message landed on a bad week, they are unsure what to say, or they would rather leave that chapter closed.
All of those are allowed, and none of them tell you what you are worth. You sent something kind to someone you remember. That part already happened.
If you are still turning it over, the guide on people you used to be close to sits with the same feeling.
Reach out because you remember the person, not because you remember what they could do for you.
If that is true, the message will sound like it. If it is not, they will feel it before the second line.
Hey, you came to mind today. I realised it has been far too long. How have you been?
I walked past the place where we used to get lunch and immediately thought of you. Hope life has been treating you well.
Hi. This is slightly out of nowhere, but I was thinking about our time working together and wanted to say hello. How are things with you?
Hey, I know we have not spoken since the old work days, but you came to mind and I wanted to check in. Hope you are doing well.
I have genuinely wanted to catch up. I also have a work question I may ask later, but I did not want to pretend that was the only reason I reached out.
Sometimes the hard part is not knowing what to write. It is not knowing whether hearing from you would be welcome.
Boop lets you add someone you already know to your private list and send an anonymous Boop. If they Boop you too, names reveal and a private chat opens. If not, nothing is revealed.
Find out if the thought is mutual
No. Most people read it as a compliment rather than an intrusion. What makes it land oddly is length, not delay. A three-line hello after five years reads better than a five-paragraph explanation after five months.
Put one human reason in the first message and no request in it at all. If your opening line mentions your role, their role, or an industry, rewrite it. Anything that could be copied and pasted to another contact reads as outreach.
Say it plainly if you already know you will ask, because they will notice later anyway. If it is only a vague possibility, leave it out and let the conversation restart on its own. The rule is honesty about your intent, not a full agenda in message one.
That still counts. Shared hours build a real relationship even when it never left the building. Name the setting instead of pretending you were old friends, something like a specific project or a shared routine, and let them decide how much to pick up.
Use whatever the relationship already used. Slack humour usually translates to text. A purely professional relationship translates to email or LinkedIn. Do not go hunting for a number they never gave you, and do not send the same message on three channels at once.