Are You Interesting or Interested?

I have a SUPERPOWER. I always sit next to the most interesting person on the airplane. How do I know? Because I tell them so. When I settle into my seat, I sometimes turn to my seatmate and say, “Did you know I have a superpower? I always sit next to the most interesting person on the plane.” Usually, I get a side-eye, a tilted head, and a confused “WHAT?!” Then something funny happens. They start telling me what makes them interesting. And I love it.

I’ve met some fascinating people at 35,000 feet. An NFL referee, an eyewear business owner, a traveling nurse preparing to spend three years in Qatar, and a woman who writes for National Geographic and has traveled the world. (More on her later!) Think about that. All those stories sitting right next to me, just waiting to be discovered. It makes me wonder how many interesting people we encounter every day without ever learning what makes them interesting.

I’ve also learned there’s a big difference between conversational cul-de-sacs and on-ramps. A conversational cul-de-sac is a question that goes nowhere. “Going to Orlando?” Well, I sure hope so. We’re on the same plane. And just like that, we’ve reached a dead end. Time for an awkward three-point turn.

A conversational on-ramp gives people somewhere to go. Instead of “Going to Orlando?” try “What’s taking you to Orlando?” And one of my all-time favorites is “Who did you see at your first concert?” Oh, the stories that come out of that one! Someone inevitably says, “Well, my parents dragged me to see so-and-so at the county fair. Does that count?” Of course it counts! And suddenly we’re off and running.

Small talk isn’t necessarily bad. Sometimes it’s how we get the conversation moving. The problem is when we stall out before we ever merge onto the highway. Think about the last conversation you really enjoyed. The kind where you lost track of time, laughed unexpectedly, or walked away thinking, “What an interesting person!” Chances are, someone was genuinely curious.

And curiosity is something we could all use a little more of, especially in a world where we’re constantly communicating but not always connecting. We send texts, attend meetings, and scroll through social media all day long. We’re surrounded by communication, yet sometimes starving for connection. The solution isn’t necessarily to talk more. It’s to get better at inviting other people into the conversation.

You don’t need a pocketful of clever conversation starters. You just need to be curious enough to ask a good follow-up question. Someone mentions a vacation? Ask what surprised them. A new hobby? Find out how they got started. You’d be amazed at what people will share when they realize you’re actually interested in the answer.

Of course, we’ve all been trapped in conversations where someone just keeps talking, and we’re desperately searching for a polite way out. Every time you think the story is wrapping up, here comes another one! And sometimes WE’RE the ones doing all the talking, completely missing the signals that someone else is ready to move on. Being a great conversationalist isn’t just about knowing how to start a conversation. It’s also about knowing when to stop talking and start listening.

Sometimes the best response isn’t another story. It’s “Tell me more.” Or “What happened next?” Being interesting might get someone’s attention, but being interested is what builds a connection.

Of course, not everybody wants to merge. Remember that National Geographic writer I mentioned earlier? There’s a little more to that story. When I sat down next to her and announced my superpower, she was clearly NOT impressed. She gave me an Olympic-level eye roll and went straight back to her book. Message received. I put on my headphones, went about my business, and didn’t say another peep.

Halfway through the flight, she tapped me and asked me to take my headphones off. Turns out, she was a writer for National Geographic who had traveled all over the world. WHAT?! Now that’s interesting! I couldn’t resist asking why she’d decided to tell me. Her answer? “You charmed it out of me.” Charmed it out of her? I hadn’t said a WORD since she’d rolled her eyes! I was just minding my own business. But maybe that was the point. Sometimes the best way to connect with someone is to give them the space to decide whether they want to connect with you. I can take a hint. Even at 35,000 feet.

And this matters just as much at work as it does on an airplane. Think about how often we exchange the usual “How was your weekend?” and “Busy week?” before diving straight into business. What if we occasionally asked something different? “What was the highlight of your weekend?” or “What’s something you’re looking forward to?” You might discover that the coworker you’ve known for years is training for a marathon, learning to play guitar, or planning the trip of a lifetime.

We don’t need to become best friends with everyone we meet. But when people feel noticed and heard, conversations become easier, relationships grow stronger, and everyday interactions become more enjoyable.

Here’s a little challenge. The next time you meet someone, pay attention to your first question. Is it a conversational cul-de-sac or an on-ramp? Are you giving someone room to share, or are you doing all the talking?

You don’t have to be the life of the party or have a pocketful of hilarious stories. You just need to be interested. Small talk fills the silence. Great questions build connections. And you never know where a good conversation might take you.

Especially if you’re sitting next to me on a plane.

A smartphone screen displaying a collage of selfies with various people titled Plane strangers, with the Christine Cashen logo in the top corner.


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