Let me ask you something.
Not “How are you?” in that watered-down, pass-me-the-salt kind of way.
But like—how are you really doing?
Like, on a scale from “vibing with the universe” to “eating cereal for dinner in the dark?”
How’s your brain?
How’s your heart?
How’s your skin, your spirit, your sleep, your gut health, your playlist, your posture?
Because I care. I genuinely care.
And if you care about people—even just a little—you’d be shocked at how wide they’ll open up. Sometimes too wide. Sometimes you’ll hear about their IBS flare-ups, but hey—that’s the price of human intimacy.
Here’s the Deal:
People are craving real connection like it’s avocado toast in a gluten-free desert.
But no one’s ordering it because everyone’s afraid to ask the real questions.
We’ve all gotten lazy.
Small talk. Half-smiles. The occasional “How’s work?” before sliding back into our phones like social armadillos.
But want to be interesting? REALLY interesting? Like "people-talk-about-you-after-you-leave-the-room" interesting?
Here’s the secret
Be so wildly, stupidly interested in other people that they forget you were a stranger.
Ask Questions Like You Actually Want the Answers
Let’s play a game. Instead of:
“Where are you from?”
Try:
“Where’s your family from, and if I went there tomorrow, what’s the one thing I have to eat or do before I die?”
Now we’re not talking geography.
We’re talking childhood smells, grandma’s cooking, sunsets, village weirdos, and the soccer team that always loses but has the best uniforms.
BOOM. Connection.
Other good ones:
“What’s the weirdest family tradition you secretly love?”
“What song makes you feel 14 again?”
“Did you have a ‘weird neighbor’ growing up or were you the weird neighbor?”
“If your soul had a color today, what would it be—and why?”
“What’s one story about your life that no one would believe but it’s 100% true?”
Ask these questions and then—here’s the magic—shut up.
Listen.
Let the silence hang.
Let the words come.
Because here’s the spicy, spiritual, soul-snuggling truth:
Listening is the love language of legends.
You’ll learn more from one quiet conversation than from a thousand YouTube rabbit holes. You’ll be gifted with stories that turn into lessons.
You’ll make people feel seen, and in doing that, you’ll feel seen too.
What Happens Next?
You’ll start caring about things you never thought you would.
Armenian folk dancing. Jamaican sea moss smoothies. Why someone’s dad cried at a Bruce Springsteen concert.
Suddenly, your life is full. You’re interesting. People gravitate toward you—not because you talk well, but because you listen like it matters.
Because it does.
TL;DR For the Attention-Deficient Delightfully Curious:
Want to be interesting? Start by being wildly interested.
Ask better questions. The kind with color, flavor, and memory.
Shut up and listen. Then keep listening. Then ask more.
You don’t have to be smart. You just have to be curious.
CALL TO ACTION: BE A WEIRDLY CURIOUS HUMAN
👉 This week, I dare you:
Pick one person and ask them a real question. Not “How are you?” but “No seriously—how are you really doing?”
Then let them answer. No distractions. Just ears, eyes, and heart.
DM me the wildest, most beautiful, or hilarious thing you learned this week @The_Shipsters_Puns and I’ll shout out the best ones in next week’s newsletter.
Or better yet—share this post, tag someone, and ask them the one question you wish someone would ask you.
Let’s make the world a little more curious.
A little more real.
And a hell of a lot more interesting.
Stay weird. Stay open.
Todd
