The Epidemic of Awkwardness

We’re living in the most connected time in human history. Smartphones, Social media, Zoom calls, Slack channels, podcasts, etc. We've never had more ways to communicate with each other.

But, the ability to genuinely connect with one another is at an all-time low. While all this technology makes us more visible, it’s making it harder to see each other. Ironically, there’s never been a more vital time for us to connect with one another and it’s never been more difficult.

We scroll through social media posts daily yet struggle to maintain eye contact during in-person conversations. We debate vociferously online but seldom debate anyone face to face. We text our friends but the actual telephone feels enormously heavy in our hands.

The Pandemic

Remember the pandemic? People were forced to shelter-in-place. Work migrated to the home. All social interaction ceased to exist. As a result, we simply lost our social agility.

Deprived of casual, spontaneous and organized social interaction, the extroverts bordered on despair. Meanwhile the introverts cheered for more.

FOMO vs. FOGO

Years after the pandemic it seems a low-grade fever of social anxiety remains. It’s as if people are suffering from a different epidemic. The epidemic of social awkwardness. Our social skills atrophied like an injured muscle wastes from lack of use.

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Prior to the pandemic we suffered from F.O.M.O. or Fear of Missing Out. Years later that F.O.M.O. has turned into F.O.G.O. or Fear of Going Out. Not from a contagion standpoint, but from a mild case of social anxiety.

People simply learned that social interaction was hard. It’s just easier to stay at-home and watch one of the myriad of networks vying for our attention. Taking a shower, getting dressed and showing up takes energy. Energy that we’ve simply lost. The R.O.I. doesn’t seem to be there anymore.

But, the good news is that within our awkwardness I sense a growing hunger for connection. And, not just human connection. A hunger for relationships that transcend superficiality and digital interaction.

David Brooks argues persuasively in his book, How to Know a Person that truly seeing others is both a practical skill and a moral imperative. In this hyper-connected, socially distant era, “knowing someone” is a rare gift.

And, to really know a person you need to listen more than you talk. I wrote about this recently in We Are Drowning in Words While Starving for Wisdom. It’s been read by over 27,000 people.

I came up with a few sample questions to “stimmy” those deeper connections? Some are inspired by David Brooks. Here’s a couple for you to try:

1. What do you have faith in right now?

This question bypasses religion, money and politics to get at something more fundamental: when everything (money, power, pleasure & relevance) is stripped away, what is it that remains? What is it that is still true about you?  (If you’ve watched this season of The White Lotus this question will ring true.) 

2. What’s really going on in your life right now?

The magic is in the word “really.” It announces that you’re allowed to push beyond the superficial conversational platitudes. That you already know everything isn’t ”fine” and that “the old man’s a hassle and the kids have the flu”. If done correctly, the answer won’t be short.

3. What’s the best thing that ever happened to you?

This question invites joy and gratitude into the conversation. It reveals priorities and values. And surprisingly, the answers rarely involve material possessions or achievements. They’re almost always about connections, moments of true grace or personal transformation.

I wrote more about this question back in October 2025 in The Entropic Nature of Aging.

4. What’s the one thing nobody really knows about you?

This question acknowledges that we all have hidden dimensions. It honors the fact that what we show the world is just the tip of the iceberg.

5. What is the one thing you wish you’d done differently?

Regret is universal but rarely discussed. This question invites reflection without judgment. It creates space for vulnerability and often reveals what someone values most.

6. What’s the one event or decision that made you who you are?

Identity doesn’t form gradually—it crystallizes around pivotal moments. This question invites the sharing of their story or origin, not as a timeline of events but as a narrative of becoming themselves.

The Lost Art of Listening

Profound questions are only half the equation. The other half is profound listening.

Most people don’t listen; they simply wait for their turn to talk. They’re so busy formulating their next brilliant statement that they miss the gift being offered in the answer.

When you ask a profound question, you’re making a promise to truly hear the answer—to bear witness to someone else’s reality without judgment or agenda.

The Risk Worth Taking

Deeper questions involve risk. They might be met with awkward silence or superficial deflection.

That’s okay. Not every conversation needs to feel like an episode of Dr. Phil. But when the moment is right—when there’s enough daylight, enough trust, enough courage—a single question can transform our connection to another person.

With endless small talk and constant digital distraction, asking questions that matter might be the most radical act of connection we can offer. It says: I see you. I’m curious about you. Your story matters to me.

And in that invitation, we remember what it means to be human together.

I write just for the fun of interacting with people like you. Leave a comment below. I promise to read (listen) and respond to you. Hey, maybe we’ll end up being friends.

Hey, real quick, if you learned something from this article or it makes you think differently about your conversations, would you mind forwarding it to someone you care about?