Hi {{first_name|there}}, it’s Thomas.

The older we get, the more we understand the real value of a good friend. Not just someone who texts back or likes your post, but the kind of friend who energizes you. The one who gets your sense of humor. Who asks how your big presentation went. Who shows up.

And yet, despite our appreciation, most of us don’t see those friends nearly as often as we’d like.

Because life gets busy. People have kids, demanding jobs, caregiving responsibilities, moves, marriages, divorces, renovations, travel plans, and burnout cycles. The modern adult schedule is a logistical nightmare, at best.

So how do you make sure that your most cherished friendships don’t fade into “sometime soon” territory?

Turns out, it might be as easy as adding one simple question to your repertoire.

This may be the most underrated relationship move you can make. Ask it at the end of a hangout, walk, coffee, lunch, or phone call with someone you know you want to keep close.

It does three things all at once:

It’s proactive. It’s generous. It’s efficient.

And maybe most importantly, it helps break the cycle of inertia.

We’ll explore why it’s so good after a word from this week’s sponsor.

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Support your Resolutions

Psychologists and sociologists alike have long emphasized the importance of repeated, intentional contact in relationship maintenance. As far back as the 1950s, social psychologist Leon Festinger showed that frequency of interaction—especially in informal settings—was one of the best predictors of friendship formation and retention.

More recent studies, like the work of Dr. Jeffrey Hall at the University of Kansas, suggest it takes about 50 hours of interaction to move from acquaintance to casual friend, 90 hours to become real friends, and more than 200 to become close. But those hours don’t accumulate unless you keep seeing each other.

So don’t leave the next interaction to chance. If you’ve had a good time, say so, and take one step toward securing the next one. Make it even more potent by adding it to both of your calendars.

A lot of us worry about seeming “too eager.” But this question isn’t clingy. It’s clear. It signals that you know what matters and who matters. And most people are grateful for a friend who takes the guesswork out of scheduling.

It also subtly shifts your friendship out of the “someday” zone and into a habit. If even a handful of your best friends begin hearing this question from you, you’ll notice something start to change: your most meaningful connections will become more frequent, more natural, and more emotionally sustaining.

Of course, this isn’t something to say to every casual acquaintance. It’s for the people you’re confident you want more of in your life.

Maybe you’ve got three of them. Maybe seven. Maybe one. That’s fine. This isn’t about volume; it’s about depth. It’s about making sure that the people who fill your cup actually stay on your calendar.

Think of it as an investment in relationship momentum. The more consistently you see someone, the less each hangout has to carry. You’re not always catching up; you’re just picking up where you left off.

Think of one friend you always love seeing, but rarely do.

Reach out and schedule time together this week. When you meet, enjoy it. Be fully present.

And as the conversation winds down, ask: “When’s the next time I’ll see you?”

Then, make a plan and put it on your calendar.

It doesn’t have to be elaborate. A walk next weekend. A check-in call in three weeks. A Tuesday lunch. Doesn’t matter.

What matters is you’ve turned a fleeting moment into a recurring connection.

That’s how real friendships stay alive.

And it starts with just one question.

What’s been your experience explicitly asking for the next time? Do you have something you think could help others? Just hit reply — your email goes straight to my inbox. 🙏

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