How to reconnect with an old colleague
Nobody is offended that you went quiet for five years. They're put off by a message that takes four paragraphs to say what it wants.
By Jerry Feng, Growth at Happenstance. Updated August 28, 2026.
The short version
Name the gap without apologizing for it, lead with one specific thing only the two of you remember, and say what you want by the fourth line. Long silences between colleagues are normal and rarely held against anyone. The message that fails is the vague catch-up, because it asks the reader to work out what you want.
Why the specific memory beats the catch-up
Writing to somebody after three years of silence feels like using them. It usually isn't, and there's research on exactly this. Work on dormant ties, the people you've not been in contact with for three years or more, found that when executives went back to them for advice on a real project, the answers were as valuable as those from their current connections, and more novel (MIT Sloan Management Review, 2011). They know things you don't precisely because you stopped talking.
The gap is not the problem. The message is. Two versions of it fail. A vague catch-up hands the reader nothing to answer, so they have to invent a reason to write back, and that gets postponed forever. A buried ask spends three friendly paragraphs and then asks for a referral in the last line, which reads as a tactic even when it was only nerves.
One specific memory fixes the vague version. The deployment that failed at midnight, the client who kept rescheduling, the person you both found difficult. A mail merge can't produce any of those, and they put the reader back in a room with you. Then say what you want, since being direct is what keeps the warm part from reading as a setup.
Doing this with Happenstance
Most of the difficulty here is memory. You know twenty people from two jobs ago are worth writing to, and you cannot name them on demand, so nobody hears from you. Happenstance reads the accounts you connect, including email headers and your calendar, so it knows who you worked alongside and how well you know each of them. Ask “Who did I work with at Ardent?” and you get the list, with where each person is now.
Happenstance is free. The free plan is the whole product, with usage limits on chat and web searches beyond your network. Pro raises the limits: unlimited web searches and results, higher chat limits, and CSV export. If the reconnection is part of a job search, the workflow around it is on Happenstance for job seekers.
Two messages, depending on what you want
Use the first when you need something and the second when you do not, which is a better reason to write than most people think.
Subject: [Shared detail], and a favor
2. When you want nothing, yet
Subject: Thought of you when [the trigger]
If the reason you are writing is that they can introduce you to somebody, send the second message first and the ask a week later. What to put in that second message is covered in asking for a warm introduction.
What Happenstance can see
Email is read as headers only. Message content and attachments never reach our servers. Yes. Your connections are searchable only by you, the friends you accept, and the groups you join, and sharing is always mutual. Your public profile shows a constellation of named people you know by default, which you can turn off anytime. We never share, sell, or use your data to train AI models. Happenstance is SOC 2 certified and DTI Trust Level 2; the full list of what is stored and for how long is on the security page.
Frequently asked questions
What do you say to an old colleague you haven't spoken to in years?
Open with something only the two of you'd remember, name how long it has been in a neutral way, and say why you're writing. A specific memory does the work that an apology cannot: it proves you're writing to them rather than to a list.
How do you reconnect without seeming like you only want something?
By saying what you want. The reader will work it out in either case, and the version where you said it plainly reads as respect for their time. What creates the bad impression is three paragraphs of warmth followed by an ask in the last line.
Is it OK to ask an old colleague for a job referral?
Yes, and it's one of the most common reasons people reconnect. Give them the job link and two lines they can paste, and ask straight out. Someone who worked with you for a year knows enough to answer.
Should I email or send a LinkedIn message?
Email if you have an address that still works, because it survives forwarding and sits in a place people answer. LinkedIn if the email is stale or you never had one. Don't send both at once, which reads as pressure rather than diligence.
How long is too long to reconnect?
There is no ceiling. Research on dormant ties defines them as people you haven't been in contact with for three years or more, and it found their advice as useful as advice from current connections. Ten years is unremarkable, and the shared history doesn't expire.
What if they don't reply?
Leave it. One follow-up after two weeks is fine if you have something new to add, and after that the silence is the answer. It usually means a busy month rather than a judgment about you, and reaching out again in six months is entirely normal.
Make your own luck
Join 500,000+ professionals already searching their whole network.
Continue with Google