You're probably not asking your friends enough questions.
This month’s Friendship Challenge is simple but powerful: ask your friends more questions. (Way more than you think you should.) Trust me, people notice when you're not asking questions.
One of my most viral TikToks from last fall was when I talked about "the friend who never asks about you." It has over 90K views and over 400 comments. People had NEGATIVE feelings and lots to say about friends who don't ask questions.
To help us all do better with asking questions, I discussed one chapter from a book I loved earlier this year called Talk: The Science of Conversation and the Art of Being Ourselves by Harvard Business School professor Alison Wood Brooks.
This month's challenge is about getting curious about your friends, deeply curious. Most of us think we ask plenty of questions, but research shows we don’t.
To help you get started:
- Ask more questions than feels natural.
- Stick with follow-ups instead of jumping from topic to topic.
- Use what questions at first more than why to avoid being intrusive, but you can move to why eventually.
- Listen. Listening is how you know what follow-up questions to ask next.
When you’re interested, you become interesting.
And hey, as June’s challenge reminded us, it’s okay to ask for a favor. So here’s mine: Please share an episode with a friend (just maybe not THIS one if you’re trying to send a message as that's too passive-aggressive 😉).
Find all the 2025 Friendship Challenges at DearNina.Substack.com.
LINKS AND RESOURCES:
- 2025 Dear Nina Friendship Challenge overview
- Great book on the art of conversation! Talk: The Science of Conversation and the Art of Being Ourselves by Alison Wood Brooks
ALL THE DEAR NINA LINKS + CONTACT INFO
📢 How to promote your service, business, or book on Dear Nina
📱 Subscribe to my newsletter “Conversations About Friendship” on Substack
❤️ Instagram, TikTok, YouTube, & the Dear Nina Facebook group
📪 Ask an anonymous friendship question
🔎 Want to work with me on your podcast, your friendships, or need another link? That’s probably here.
Advertising Inquiries: https://redcircle.com/brands
Popular Podcasts
CrimeLess: Hillbilly Heist
It’s 1996 in rural North Carolina, and an oddball crew makes history when they pull off America’s third largest cash heist. But it’s all downhill from there. Join host Johnny Knoxville as he unspools a wild and woolly tale about a group of regular ‘ol folks who risked it all for a chance at a better life. CrimeLess: Hillbilly Heist answers the question: what would you do with 17.3 million dollars? The answer includes diamond rings, mansions, velvet Elvis paintings, plus a run for the border, murder-for-hire-plots, and FBI busts.
Crime Junkie
Does hearing about a true crime case always leave you scouring the internet for the truth behind the story? Dive into your next mystery with Crime Junkie. Every Monday, join your host Ashley Flowers as she unravels all the details of infamous and underreported true crime cases with her best friend Brit Prawat. From cold cases to missing persons and heroes in our community who seek justice, Crime Junkie is your destination for theories and stories you won’t hear anywhere else. Whether you're a seasoned true crime enthusiast or new to the genre, you'll find yourself on the edge of your seat awaiting a new episode every Monday. If you can never get enough true crime... Congratulations, you’ve found your people. Follow to join a community of Crime Junkies! Crime Junkie is presented by audiochuck Media Company.
Stuff You Should Know
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.