How to Make Boring People Less Boring

Some people are so boring that about the only value you can get out of dealing with them is gossiping about them after you escape. Here’s a way you can get a bit more value, especially if you can’t escape: Try to make them less boring.

We’re so used to being entertained well these days that it’s easy to forget that it takes two to make a conversation. We aren’t couch potatoes. Other people aren’t our dancing monkeys who owe us the old razzle-dazzle. We can get proactive to make boring people less boring. It’s worth a try, anyway.

First, recognize why people get boring, and this is true of any of us. When we’re talking, our priority tends to be saying what we need to hear not necessarily what others need to hear. And what do we need to hear ourselves say? That we’re good people, at minimum innocent, at maximum exceptionally great.

People get boring when there’s too much of that, too many self-affirming station identifications, too much name- and credential-dropping, too many long, detailed tales of their daring exploits apropos nothing where you just have to sit there while they do the equivalent of drunk singing, them not listening to how they sound, just lost in self-affirming reverie, feeling like a rock star. Such self-advertising is to good conversation what ads are to good show: boring interruptions, especially boring if we’re just waiting our turn to do the same.

It’s natural that people would lean on us like that, like drunks leaning on a lamppost, as if we’re just a warm body to talk at, an extra in the movie they star in, a prop that can listen all day to their self-glory stories.

It’s especially natural when you step back to remember what we humans are. We’re these mid-sized mammals wrangling this newfangled contraption called language. Language makes us an especially anxious species, able to imagine way more threats and missed opportunities than can a dog or a chimp. Language also makes us especially prone to giving ourselves pep talks using our outside voices at anyone who we can get to listen to us.

We all do it. Powerful people, spoiled by attentive audiences, expect to be maintained in the manner to which they’re accustomed. Lonely people have had no one to talk at, and are hella thirsty. People who feel heard by God or some higher power like their guru or favorite president consider themselves such experts on who’s listening that they don’t notice that you’re not. People straining to live large can get so full of themselves that they can’t imagine anyone finding them uninteresting. Aspiring influencers can’t take a break. Wannabes and wannastillbes, the folks who once were big deals but aren’t anymore, wish they were.

Aikido is a martial art that uses an opponent’s momentum to destabilize them. An opponent punches. The Aikido master dodges the punch, grabs their arm in the direction it’s moving, and pulls their opponent to the ground.

To make tedious, grandstanding, boring people more interesting, you can do that. Use their logic’s momentum to destabilize them and shut them up. There are times when that’s called for. Some folks just need to be yanked down off their high horse.

There are also times when you’ll want to use a bore’s momentum to stabilize them so they stop leaning all over you. How do you do that? By pulling on one of their threads in their mindless blather and weaving it into something more substantive. Ask them a question that builds on their momentum but makes them think like a human rather than broadcast at you like an ad.

It demonstrates what I call weavedence—evidence that you are present to weave a web of thought from what they’ve offered, evidence that you’re actually listening, not just waiting your turn to blather at them. It often gets a bore’s attention. Many bores are used to not being listened to. They rely more on your tact than your interest. Weavidence can surprise them, and even calm them down.

Bores fantasize about being interviewed. That gives you some leeway. For them, it’s just fun to be the center of attention. If you’ll grant them that they’ll follow you anywhere. They won’t even mind challenging or personal questions that force them to think. If they do mind the challenging questions, they’ll get uncomfortable and leave. Not the worst outcome when you’re trapped with a bore.

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To find such questions, think like an anthropologist. Step back and observe that you’re dealing with another human. Same repertoire as you but with a different background, temperament, and style. Use the bore as an opportunity to learn more about your kind, us humans in all our variety. We feel more alert when we get to talk, so keep the questions coming. Follow up by ferreting around in whatever you find interesting, which can include trying to figure out what made them so boring.

Turn it into a parlor game. The object is to see how deep you can get them to go into honest eye-to-eye self-reflection.

To soften the confrontation of your challenging and personal questions, use some self-effacing humor. Laugh at yourself. Maybe they’ll reciprocate by laughing at themselves. The deepest conversations are between people who can laugh at and with each other, people just sitting together shop-talking what it’s like to be human, bozos on this wayward bus. If you show that you’re one, too, maybe they’ll relax into being one also.

Or maybe they’ll go on being boring, in which case you’ll have the consolation of thoroughness as your prize. You did what you could to make them more interesting instead of acting like a couch potato waiting passively and impatiently for an extra, a dancing monkey in your docudrama who owes you entertainment.

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