10 Questions For The Deeply Curious 

 I consider myself a curious person by nature. When I’m in a social situation, I genuinely listen and ask thoughtful questions to get to know someone better. Where I struggle is small talk. There have been moments where I absolutely wanted to insert my size 8 (in need of a pedicure) foot into my mouth. Those missteps can cause my anxiety to skyrocket, but they haven’t stopped me from being curious. 

It’s been proven that curiosity can lead to stronger relationships. There were two studies done at George Mason University in which a researcher, Todd Kashdan, said this: “When you show curiosity and you ask questions and find out something interesting about another person, people disclose more, share more, and they return the favor, asking questions of you. It sets up a spiral of give and take, which fosters intimacy.”  

If you’ve been around a while, you know I’m a proud introvert. But that doesn’t mean I don’t love getting to know people! But I do think it makes me downright awkward in social settings. That’s where you come in.

The Best Question You’ve Ever Been Asked

I wanted to up my small talk game by going to my next social gathering ARMED with loads of interesting questions to ask people. Kind of like an “in case of social emergency” type list. Which led to the question we asked all of you on Instagram: “What is the best or worst question you’ve ever been asked?” And boy, did we get some great responses. 

Penn and I picked out some of our favorites to share with you on this week’s podcast. It also inspired us to come up with our own list of questions that I will promptly put into my phone in anticipation of that next cocktail party. We’ve listed them below so that you can arm yourself for the next time you and cousin Reggie are staring silently at each other at the family picnic. (You’re welcome.)

10 Questions For The Deeply Curious 

  • What’s one thing you’ve always wanted to do, but haven’t done? 
  • What is one thing about yourself that you wish more people knew about you?
  • What did you love doing as a kid that you don’t do anymore?
  • What was the most difficult conversation you ever had?
  • When do you feel most like yourself?
  • What one thing are you most proud of?
  • Who is your doppelganger?
  • Is there anything from the past that you wish would come back?
  • If you had to eat only one meal for the rest of your life what would it be?
  • If you could live anywhere in the world, where would you live?


  • What made you smile today?

We had so much fun with this one, I hope you’ll give it a listen. Do you have a really good question you ask to get a conversation going? Let me know in the comments. 

Acast: https://open.acast.com/public/streams/618c3caaa322d1001350082c/episodes/661c6d51aed7bb0016dba6bd.mp3

Apple Podcasts: https://podcasts.apple.com/us/podcast/the-holderness-family-podcast/id1378725018?i=1000652582675

Spotify: https://open.spotify.com/episode/5GtL6Kvoy6q9D0KszPZ8mT?si=95327f9498074e1f

Pandora: https://pandora.app.link/ukTw5r1bQIb

Amazon: https://music.amazon.com/podcasts/094464e9-aad9-4b09-8ee8-248c76b48bd6/episodes/b6374c5c-d807-4358-8313-808814795154/the-holderness-family-podcast-the-worst-questions-ever-and-the-best