The Message She Almost Didn't Send
Claire had been connected with David on LinkedIn for three years. They'd met at a conference, had a great conversation about content marketing, exchanged messages for a few weeks, and then… nothing. Life got busy. Projects piled up. And suddenly it had been two years since they'd last spoken.
Now Claire was launching a new agency and David's expertise would be perfect for a project she had in mind. But every time she went to message him, she froze. Won't it be weird to reach out after all this time? Will he think I'm only messaging because I need something? Should I pretend we've been in touch the whole time, or acknowledge the gap?
She almost didn't send the message. But then she decided to be honest. She wrote: "Hey David—it's been way too long since we last chatted. I've been following your work from afar and I'm continually impressed. I'm launching a new agency and I'd love to get your take on something if you have 10 minutes in the next couple weeks. No pressure if now's not a good time!"
David replied within an hour: "Claire! Great to hear from you. Congrats on the agency—I'd love to catch up. How's next Tuesday at 2pm?"
The conversation turned into a consulting relationship. The consulting relationship turned into a referral partnership. And it all started with a message Claire almost didn't send because she felt guilty about the gap.
Here's the truth: reconnecting on LinkedIn doesn't have to be awkward. People understand that life gets busy. Connections go dormant. And when you reach back out with honesty, warmth, and respect, most people are happy to re-engage. In this guide, you'll learn exactly how to craft a reconnect LinkedIn message that feels natural, authentic, and effective—no guilt required.
Why Reconnecting Feels Awkward (And Why It Shouldn't)
Most people hesitate to reconnect because they're worried about coming across as opportunistic or transactional. I haven't talked to them in months, and now I'm suddenly reaching out because I need something? That's so transparent.
But here's the thing: people expect this. Professional relationships are inherently utility-based. That's not a bad thing—it's just reality. You don't stay in constant touch with every single connection. You re-engage when there's a reason to. And as long as you're respectful, honest, and clear about why you're reaching out, most people appreciate the directness.
In fact, research on social reconnection shows that people overestimate how awkward it will be to reach back out. The person on the receiving end is almost always more receptive than you think. They're not sitting there judging you for the gap—they're just happy to hear from you.
So drop the guilt. Acknowledge the gap if it feels right, but don't over-apologize or make it weird. Just be human, be honest, and move forward. This mindset is the same one that powers effective LinkedIn DM tone: authenticity beats perfection.
The 3-Message Sequence for Reconnecting
Reconnecting isn't a one-message game. It's a sequence. Here's the structure that works:
Message 1: The Reconnect (The Honest Opener)
Your first message should do three things:
- Acknowledge the gap (briefly): "It's been a while since we last chatted..."
- Reference something specific about them: "I've been following your work on [topic]..."
- Make a small, clear ask: "Would you be open to a quick call?" or "Mind if I ask you a quick question?"
Example:
"Hey [Name]—it's been way too long since we last connected. I've been following your posts on AI in marketing and they've been super insightful. I'm working on something I think you'd have great perspective on—would you be open to a 15-minute call in the next couple weeks? Totally fine if now's not a good time!"
Notice what this does: it's warm, it's specific, it acknowledges the gap without dwelling on it, and it makes a clear, low-pressure ask. It doesn't pretend you've been in touch the whole time, but it also doesn't grovel. It's just honest.
Message 2: The Thank-You (After They Reply)
When they say yes, send a quick thank-you that confirms the next step:
Example:
"Awesome—thanks! How's Tuesday at 2pm? I'll send a calendar invite. Looking forward to catching up."
Keep it short and logistics-focused. Don't over-explain or rehash the gap again. Just move forward.
Message 3: The Follow-Up (After the Call or Interaction)
After your call or interaction, send a follow-up that reinforces the value of the conversation and keeps the door open for future contact:
Example:
"Thanks again for making time to chat today, [Name]. Your insights on [specific topic] were super helpful and gave me a lot to think about. Let's not wait another two years to catch up—I'll stay in touch. If there's anything I can ever help with on your end, just let me know!"
This closes the loop, expresses gratitude, and subtly resets the relationship. You're signaling that this isn't a one-time extraction—you're open to ongoing connection.
Four Situational Reconnect Message Templates
Different situations call for slightly different approaches. Here are four templates for common reconnection scenarios:
1. Reconnecting After a Job Change (Theirs)
Template:
"Hey [Name]—saw you made the move to [Company]. Congrats! I know we haven't caught up in a while, but I've been following your career and it's been fun to watch. How's the new role treating you? Would love to hear what you're working on if you have time for a quick call."
Why it works: Their job change is a natural conversation hook. It gives you a reason to reach out that feels timely and relevant—not random.
2. Reconnecting After a Job Change (Yours)
Template:
"Hey [Name]—it's been a minute! I recently started a new role at [Company] and it made me think of you. I remember our conversation about [topic] and I'd love to get your take on something I'm working on now. Any chance you're free for a quick chat in the next couple weeks?"
Why it works: Your transition creates a natural re-entry point. You're not just reaching out randomly—you have news, and that news connects to them.
3. Reconnecting Around a New Project or Product
Template:
"Hey [Name]—it's been too long! I'm launching [project/product] and I immediately thought of you because of your expertise in [area]. Would you be open to a quick call to get your feedback? I'd really value your perspective. No pressure if timing's not great!"
Why it works: You're asking for their expertise, which is flattering. And you're being clear about why you're reaching out, which removes the guesswork. This is similar to how effective micro-asks work: you're making the request specific and easy to evaluate.
4. Reconnecting After an Event or Shared Experience
Template:
"Hey [Name]—I saw you attended [event/webinar]. We haven't caught up in forever, but I was there too and your question during the Q&A was spot on. Would love to compare notes if you have 15 minutes this week. Coffee's on me (virtually, of course)."
Why it works: Shared context makes the reconnection feel less random. You're not coming out of nowhere—you have a recent, mutual touchpoint.
What to Avoid When Reconnecting
Here's what not to do when reaching back out to dormant connections:
Don't Over-Apologize
Bad: "I'm so sorry for not staying in touch. I feel terrible that it's been this long. I should have reached out sooner. I hope you don't think I'm a bad person for disappearing..."
Better: "It's been a while since we last chatted—hope you've been well!"
Acknowledge the gap briefly, then move on. Don't wallow in it. Over-apologizing makes it more awkward, not less.
Don't Pretend You've Been in Touch
Bad: "As we discussed previously..." (when you haven't spoken in two years)
Better: "I know it's been a while, but I wanted to reach back out because..."
People know when you're being fake. Just acknowledge reality honestly.
Don't Lead with a Big Ask
Bad: "Hey, long time no talk! Can you introduce me to your CEO?"
Better: "Hey, long time no talk! Would you be open to a quick 10-minute call to catch up?"
Start small. Rebuild rapport before asking for significant favors. This mirrors the same gradual trust-building you'd use when learning to ask for a call on LinkedIn: earn the right to make bigger asks over time.
Don't Send Obviously Generic Templates
Bad: "Hi [Name], I hope this message finds you well. I wanted to reconnect and explore potential synergies between our organizations."
Better: "Hey [Name]—it's been too long! I saw your recent post about [specific topic] and it reminded me of our conversation back at [event]. Would love to catch up if you have time."
Personalization matters. Reference something specific—a past conversation, a recent post, a shared connection. Show that this isn't a mass blast.
When to Reconnect (And When to Let It Go)
Not every dormant connection is worth reviving. Here's how to decide:
Good Reasons to Reconnect:
- You have a specific reason that benefits both of you (collaboration opportunity, shared interest, mutual help).
- They've posted or done something that genuinely interests you and provides a natural conversation hook.
- You're entering a new phase (new job, new project) that aligns with their expertise or interests.
- Enough time has passed (at least a few months) that reaching out feels natural, not desperate.
Bad Reasons to Reconnect:
- You're just collecting connections for the sake of it.
- You're trying to pitch them something they clearly won't be interested in.
- The relationship was always one-sided and they never really engaged with you.
- You're reaching out purely out of obligation, not genuine interest.
If you don't have a real reason to reconnect, don't force it. Quality beats quantity. Focus on the connections that matter, not the ones that just fill out your network.
How to Keep the Relationship Alive After Reconnecting
Reconnecting is great—but if you ghost them again immediately after getting what you need, you've burned the bridge for good. Here's how to keep the relationship warm after you reconnect:
- Engage with their content occasionally. Like, comment on, or share their posts every few weeks. Low effort, high impact.
- Send periodic check-ins. Every few months, send a quick "Hey, how's [project] going?" message. Stay on their radar without being needy.
- Offer value when you can. Share an article they'd like, make an intro, offer feedback. Give before you ask again.
- Set reminders. Use a CRM, ANDI, or just calendar reminders to prompt yourself to check in. Out of sight = out of mind. Don't let the relationship go dormant again by accident.
The best networkers don't just reconnect—they stay connected. They build systems to maintain relationships over time, not just revive them when convenient. Learn more about this approach in our guide to building lasting LinkedIn relationships.
Frequently Asked Questions
How long is too long to reconnect?
There's no hard rule, but anything under five years is generally fine, especially if you had a meaningful initial connection. After five years, you'll want to provide more context about why you're reaching back out and acknowledge the longer gap more directly. The key is being honest about the timeline rather than pretending it hasn't been that long.
What if they don't reply to my reconnect message?
Don't take it personally. People are busy, inboxes get buried, and sometimes the timing just isn't right. Wait two weeks, then send one polite follow-up: "Hey [Name]—just bumping this up in case it got buried. Totally understand if now's not a good time!" If they still don't reply, let it go and move on.
Should I explain why I went silent in the first place?
Only if it's brief and relevant. "Life got busy" or "I was heads-down on a big project" is fine. But don't write a three-paragraph explanation—it makes the gap feel like a bigger deal than it is. A simple acknowledgment is enough: "It's been too long—hope you've been well!"
Next step: Never let relationships go cold again — Try ANDI Free.
