Conversation isn't a performance. It's a scavenger hunt
I had never been on a second date.
In February of 2021, snowpocalypse was finally melting in Austin. I had no power for three days, lived on trail mix, and melted snow for water. But I was still more stressed about this date.
Where do we go? What’s left to talk about? What if it’s awkward?
It felt like there could be two disasters this week. And although I didn’t realize it yet, all that anxiety came from one mistake.
I forgot that conversation isn’t a performance.
It’s a scavenger hunt.
When curiosity replaces anxiety
I realized the only thing that really mattered was getting to know each other. So I created a game to make that fun.
To play, we had to find household items at IKEA and answer a personal question for each one. Like this:
Find a plate. When have you had to eat humble pie?
But as I was making the game, a weird thing happened.
I started to feel excited instead of anxious. I stopped worrying about how the conversation could fail. I was focused on discovering things about someone I might like.
How to play the scavenger hunt
If you want to find what’s interesting about people, follow the why behind what they say.
Instead of asking the boring, “What do you do?”, play the scavenger hunt.

Work: “Tell me why you chose your job and I’ll try to guess it”
School: “Tell me why you chose your major and I’ll try to guess it”
Keep guessing, ask for hints, and make it fun. You’ll spark real conversation and uncover something interesting.
I know I did.
Curiosity is memorable
We were at IKEA for three hours, and I lost track of time.
And I never lose track of time.
Later that night, she asked if I could send her the scavenger hunt so she could remember it. I didn’t want to forget the day either.
Good thing we’re now married.
I can’t promise you’re one conversation away from meeting your spouse, but I can say people will remember you being curious about them.
Your Turn
Conversation gets easier when curiosity replaces performance. So next time you’re talking to someone, play the scavenger hunt. Everybody wins.
Love,
-T.O
P.S. I’m building a confidence game called Roadmap to help make this fun. If you’re curious, you can check it out here!