Your 5-Minute Weekly Check-In Routine for Real Connections

By Edward Kennedy

The Real Reason You Lose Touch

I lost touch with my friend Amy. Not because of a fight or anything dramatic. We just... stopped texting. She had a baby. I got a new job. Six months passed, then a year. When I finally thought about calling, it felt like I needed a reason. I never found one.

Most people don't lose touch on purpose. Life happens. Work piles up. Weeks turn into months. By the time you remember someone, it feels awkward—like you owe them an explanation for your absence.

A five-minute weekly check-in fixes this. Not by making you a superhuman connector. By removing the friction.

The Routine

Pick a time. Sunday morning with coffee. Wednesday lunch. Friday afternoon when your brain is fried. Five minutes, same time each week. That's it.

During those five minutes, you contact one person you haven't talked to recently. That's the whole system.

Who Belongs on Your List

Your list should mix people you actually want in your life. Not people you feel obligated to track. Not your entire high school class.

Start with five names:

  • Your sister who lives three states away and you miss
  • A friend from your last job who made you laugh every day
  • The neighbor who moved last year and you keep meaning to call
  • Your old roommate who knew you before you got your life together
  • That mentor who gave you solid advice when you were starting out

Don't overthink the categories. If you miss them, they belong on the list. If you feel guilty about not calling them, they belong on the list. If you think "I wonder what they're up to" more than once a year, they belong on the list.

What to Actually Say

Keep it stupidly simple. You're not writing a novel. You're not pitching a business deal. You're sending a digital wave across the void.

Try these:

  • "Hey, thought of you today. How's life?"
  • "Remember that pizza place we used to go to? Just drove past it."
  • "Saw your name and realized it's been too long. What's new?"
  • "Your kid's birthday was last month, right? How did it go?"

The message doesn't matter. The fact that you sent it does. A bad message sent beats a perfect message drafted forever.

Family: The Weekly Thread

My brother and I text every Sunday. Same time, no agenda. Sometimes it's three messages. Sometimes it's twenty. The rhythm means we never have that "we should catch up sometime" conversation that never happens.

It started when he had his first kid. I kept forgetting to ask how things were going. Now, every Sunday at 10am, my phone buzzes with his message about the week's chaos. I reply. We stay in each other's lives without scheduling a single video call.

Acquaintances: The Quarterly Ping

That designer you worked with on a project two years ago? The one whose work you respect? A quick "Your recent project looked incredible" takes one minute and keeps the door open.

I do this with a former client every quarter. We worked together once, liked each other, but don't have a natural reason to talk. My quarterly "saw your company in the news" text keeps us on each other's radar. Last year, that turned into a contract worth five figures. Not because I was networking. Because I stayed in touch.

The Four Rules

1. Never apologize for losing touch. Just start the conversation. "Sorry I've been MIA" makes it weird. "Hey, how are you?" is enough.

2. Don't wait for a perfect moment. The moment is now. While you're reading this, you could send a text.

3. If they don't respond, move on. Contact them again in a few months or take them off the list. No guilt. Not everyone wants to reconnect, and that's fine.

4. Keep a physical list. Five to ten names in your notes app or on paper. Rotate through it systematically. Don't trust your memory.

Making It Stick

Set a phone reminder. Put it in your calendar. Tie it to an existing habit—after your weekly grocery run, before you watch your favorite show, during your Sunday morning coffee.

The goal isn't to become someone who texts 50 people a week. It's to stop losing the people who matter because you forgot to press send. This is intentional living in its simplest form.

Track it if you want. I put a checkmark next to names after I contact them. At the end of the month, I see four or five checkmarks and know I did the thing. Simple.

When You Need a System

Some people use a simple notes app. Others prefer a dedicated tool. Extndly sends gentle reminders based on rhythms you set—weekly for close friends, monthly for acquaintances. That's it. No automation, no weird AI writing your texts. Just a nudge when it's time to check in.

You don't need a tool. A tool just removes the mental load of remembering who to contact when.

Start This Week

Open your phone. Scroll to someone you miss. Send a text. Right now. Don't overthink it.

Then set a recurring reminder for next week. Five minutes. One person.

Do that for a month and you'll have reconnected with four people you were probably going to lose. That's not a bad return on twenty minutes of effort.

The people worth keeping don't need perfect messages. They just need to know you still think about them.


Ready to never lose touch again?

Extndly helps you nurture your most important relationships effortlessly. Stay connected with the people who matter most.

Try Extndly Now

Your relationships deserve better