Dear Nina: Conversations About Friendship6 Okt 2025

#167 - Ask Your Friends (A LOT) More Questions: The October Friendship Challenge

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

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Special thank you, as always, to my assistant producer, Rebekah Jacobs!

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