How to Be More Interesting, Especially If You’re Boring

Deconstructing a surprising experience at a cocktail party to come away with five tips for how to be more interesting.


As part of the proceedings of a “2-hour cocktail party” my wife Kim was hosting last Wednesday, she interrupted our sipping and snacking to have all sixteen of us stand in a circle and take turns answering a conversation-starting question:

What’s an interesting form of media you’ve recently consumed?

The first eleven attendees answered with TV shows, books, and a couple of fun facts. (Did you know “a blue whale’s heart is the size of a car”?)

Then it was Alex’s turn.

Alex being interesting at cocktail party
Alex (far right) had our complete attention.

She answered that she’d been listening to a podcast about how to sound like the other sex. This, she explained, is a bigger challenge than you’d think for people who are transitioning. For example, to sound like a woman, a biological male needs to do more than raise the pitch of their voice. Doing so damages their vocal cords. They need to change the way they talk, alter their vocabulary choices, and ask questions differently.

Illuminated ahhs, intrigued huhs, and inquiring questions bubbled from our circle.

Everyone was interested.

Because Alex was interesting.

And if you want to be interesting, too, I think you can learn something from her—more than just how to talk like the other sex.

Bugs skimming the surface
Ironically, you’d probably be more interesting if you did a deep dive into the biology of water striders, like Elisabeth Tova Bailey and her snails.

Tip #1 to Be More Interesting:
Skip the skimming.

The least interesting people in the world are shallow.

They’re drawn to surface-level things like social media and gossip. They’re self-centered. And they’re content to judge things by their covers.

You’re probably aware of this already. Most people are. But, these days, the pool of shallow people is deeper than ever.


Because there’s so much “interesting” stuff going on.

Too much. Funny dances on TikTok. Disasters in other countries. Teenagers making millions in crypto. Famous people doing crazy things. The weather.

And the news, social media, and podcasts inundate us with it. All we can do to stay afloat is skim the surface and keep moving.

The engine that powers our surface skimming?


Nobody wants to be the bozo who misses out on what everyone else in their circles is keeping up with. So you end up vaguely aware of the same things as everyone around you—another bug in a swarm of skittering, uninteresting water striders.

But then there are the Alexes of the world. They go deep.

Chris working on his about page.
“I train people’s comfort zones.” > “I’m a blogger.”

Tip #2 to Be More Interesting:
Do something specific and useful.

Alex has an unfair advantage over most of us:

She has an unshallow job.

She’s a speech therapist who focuses on a small niche within her field. It’s fertile ground for being interesting for two reasons:

  1. She solves a problem. Solving a problem makes you part of a story. And people can’t get enough of stories. So the better you can explain how you solve a problem, the more interested people will be in what you do.
    For instance, if you bumped into me and asked me what I did, which would intrigue you more: A) I’m a blogger. B) I keep people out of ruts.
  2. She’s in a focused niche. “I’m a speech therapist specializing in people transitioning sexes” sparks more curiosity and interesting conversation than “I’m a therapist.”

Tip #3 to Being More Interesting:
Go boring in your free time.

The more you bore into a topic, hobby, or passion, the less boring you’ll be.

If you don’t believe me, read The Sound of a Wild Snail Eating.

When Elisabeth Tova Bailey was bedridden by a mysterious sickness for months, she could have watched every season of The Bachelor, learned enough trivia to win at Jeopardy!, or started a blog. Instead, she formed an intimate relationship with a snail living in the flower pot by her bed and learned all about the species.




I plowed through the book in three nights.

Another example of going deep to be interesting is, again, Alex.

In her free time, she bores deep into the South African wilderness, doing hardcore, 24-hour-plus Adventure Races and organizing multi-day treks—like the canyoning trip that introduced me to the 3-day effect. This pastime supplies her with plenty of interesting stories and insights.

Alex hiking
Alex (blue bag), leading us on an adventure.

Even my experience as a blogger supports this interesting-ing tip.

I sometimes pick a topic and go deeper into it than 99.99 percent of the world. I explore it from as many angles as possible—reading multiple books, listening to podcasts, and scouring Google Scholar. Then I extract and polish the most valuable ideas.

I’ve done so for:

Unsurprisingly, these are some of my best-performing posts.

Tip #4 to Be More Interesting:
Give people what they want.

If Alex had stopped her answer short by saying, “I’m listening to a podcast about trans people’s trouble speaking,” that wouldn’t have interested us nearly as much.

The part that caught our attention was about how men and women talk differently. Because that helped us learn a little bit about our favorite topic:


Person looking at her reflection
Always interesting.

We’re always interested in learning things that help us understand ourselves better and ideas that will make us more successful at life.

So use that to your advantage:

Before opening your mouth to try to sound interesting, ask yourself, “What’s in it for them?”

If you can’t come up with an answer, don’t bore them with it. Consider trying the next tip instead.

Tip #5 to Be More Interesting:
Ask the right questions.

Our reception to Alex’s answer wouldn’t have been as warm had she just blurted out of the blue what she’d learned about talking like the other sex. Because people need to be primed to be interested.

So try this:

Ask questions to people you hope they ask you.

  • “What’s an interesting form of media you recently consumed?”
  • “Tell me something I don’t know?”
  • “What’s a problem you’re working on solving?”

If they have interesting answers, great!

That gives you a new topic to go unusually deep into. Keep boring in by using two of my favorite tricks for being a better active listener from award-winning journalist Kate Murphy’s book, You’re Not Listening:

But what if they don’t have interesting answers?

Hopefully they’ll turn the tables and ask your questions back at you so you can shine.

If not, it may be in your best interests to avoid that person.

Before You Go Be More Interesting

Let’s recap.

To be more interesting:

  1. Skip the skimming.
  2. Do something specific and useful.
  3. Go boring in your free time.
  4. Give people what they want.
  5. Ask questions you want to be asked.

And one last tip:

End on a high note.

So with that in mind, consider this:

“Bowling would be more interesting if it were slightly uphill.”

Demetri Martin

For more on making your uphill climb through life more interesting and exciting, you might want to check these out:

About the author

👋 I'm Chris. Everything you read on is my fault. This site is like a gym for your comfort zone, full of challenges to make your status quo sexier. Join my 'Consider This' newsletter for a fun new challenge every 10 days. Try it!

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The Zag shares my adventures off of the boring beaten paths of life and ideas for finding your own unfollowable path.