The Worst Questions Ever (And The Best)

I love discovering new things about people through great conversation. But lately I’ve been thinking about how to avoid the pitfalls of asking a question that might make the other person feel uncomfortable or awkward. One of the reasons for that self-reflection is the fact that we have a junior in high school and previously, if I met up with one of her friends, I'd ask, “Where are you thinking about going to college?” I had no idea how much stress just that simple question creates. (I wrote a blog about it here!)

So this week, we asked you to send us your worst and best questions to make us laugh and help us get better! From what NOT to ask a pregnant woman to “what is the first movie that comes to mind when you think of Tim Curry?” Penn and I picked out some of our favorites to share with you on this week’s podcast. What's the best question you've ever been asked?

Special Announcement: We launched a 3-part bonus series All About ADHD! You can listen to the Part 1 now and pre-order our new book ADHD Is Awesome now!

Play Our Games

Shop Our Merch

Join Our Newsletter

Kim and Penn are online content creators known for their award-winning videos, including original music, song parodies, and comedy sketches. Their videos have resulted in over 2 billion views and 8 million followers across their social media platforms since they (accidentally) went viral in 2013. They have a best-selling book on marriage communication, a top-rated podcast, a fun-filled family card game, and most recently, they were the winners on Season 33 of The Amazing Race.

The Holderness Family Podcast is edited and engineered by Max Trujillo of Trujillo Media and produced by Ann Marie Taepke, Sam Allen, and Julie Frahm.

Follow us on YouTube

Follow us on Instagram

Follow us on TikTok

Follow us on Facebook

Hosted on Acast. See acast.com/privacy for more information.