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31 Days
31 Days

Day 2

The Lost Art of Following Up

Words by

Valet. Staff

Photography by

Aleksei Morozov

Have you noticed something? For a lot of us, a quiet shift happens as we get older. In that post-30 time of life, you still meet people you like and vibe with—new colleagues, potential collaborators, interesting acquaintances, friends of friends. Maybe you decide to exchange numbers or follow each other on Instagram. You say, “We should grab coffee,” or “Let’s hang soon.” But then … nothing.

Man contemplating follow up conversation illustration

 

It’s rarely intentional. Life fills up. Work gets louder and more demanding. Relationships consolidate. Following up starts to feel oddly heavy, like an obligation instead of a gesture. So most men don’t flake, they simply fade. The result isn’t dramatic. It’s a subtle erosion. Friendships stall. Professional connections cool. Opportunities quietly expire. The men who maintain full, interesting lives into their 30s and 40s aren’t necessarily more social. They’re just better at one unglamorous skill: closing the loop. Want to get better that? You should.

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Why It Feels Harder Than It Is

Following up asks for initiative without context. There’s no shared meeting, no group thread, no built-in reason to reach out. Just a message sent into the void. What if it feels awkward? What if they don’t respond? What if it comes off as self-interested? Psychologists note that ambiguity, not rejection, is what most people want to avoid most. And following up is all ambiguity. So men default to delay, which eventually becomes disappearance.

Vague Enthusiasm Kills Momentum

If you feel like you’ve tried to reach out before and it didn’t work, you might’ve gone about it the wrong way. Experts say that most connections die not from disinterest but from imprecision. “Let’s catch up sometime” sounds friendly but creates no forward motion. Men who are good at following up don’t overthink tone—they make it concrete. “Next week or the week after?” Or maybe something like, “Want to grab coffee near your office?” Specificity isn’t pushy. It’s respectful of time.

Timing Always Beats Polish

Social and professional momentum decays quickly. Executive coaches and recruiters often cite the same window: 24 to 72 hours. After that, interactions lose heat and become abstract. The follow-up feels less natural for both sides. A short, straightforward message sent early works better than a perfectly crafted note sent late.

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Follow up email illustration

Following Up Signals Reliability

Initiating contact doesn’t lower your status. It actually establishes it. In both friendships and work relationships, the person who follows up is often seen as organized, decisive and trustworthy. Research consistently shows people underestimate how welcome a follow-up is, and overestimate how intrusive it feels. Think of it this way: Aren’t you usually relieved when someone else takes responsibility for the next step?

Close the Loop Either Way

Following up doesn’t mean endless check-ins. Send one clear message. If it lands, move forward. If it doesn’t, let it go cleanly. The point isn’t persistence—it’s closure. Men who maintain strong networks don’t chase; they resolve. Silence is information, not a personal slight.

The easiest way to get better at following up is to stop treating it as a decision. If you enjoyed a conversation, saw potential or felt aligned, you follow up. That’s the rule. No second-guessing. No waiting for the perfect phrasing. Over time, this compounds. Friendships deepen. Work relationships strengthen. Your social and professional lives feel active rather than accidental. After 30, social continuity isn’t about being everywhere. It’s about not disappearing.

Ruth Sherman public speaking coach

“

Nothing good is ever accomplished without persistence. Because so many people are not persistent and thus fail to follow up, it is a fantastic differentiator in a world in which differentiation is harder and harder to come by.

-

Ruth Sherman, public speaking coach

31 Days
31 Days

Kick off 2026 with intention.

Every day during the month of January Valet. will be offering up clever tricks and expert tips on some of our favorite subjects, from life and work to style and grooming. Vow in 2026 to work smarter, live healthier and have a lot more fun without feeling so bogged down. 

Check back every day for new insights.

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