Every month on Dear Nina (the podcast) I offer a small challenge to deepen/revive the friendships already in our lives OR to make new friends. I say “our” because I do the challenges too. You can see the 2025 challenges here. For October: Ask your friends (A LOT) more questions!This month’s challenge is simple but powerful: ask your friends more questions. Ask way more than you think you should. Trust me, people notice when you’re not showing interest in their lives and follow-up questions are the key to demonstrating interest. 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 intense and NEGATIVE feelings on this topic and LOTS to say about friends who don’t ask questions. About three months after I made that video, I read Talk: The Science of Conversation and the Art of Being Ourselves by Harvard Business School professor Alison Wood Brooks. The letters of “TALK” stand for: Topics, Asking, Levity, and Kindness. I recommend the entire book to understand the art of connecting with your conversation partner, but this month’s Dear Nina Friendship Challenge focuses on the “A” in “TALK,” asking questions. The most impactful study Professor Brooks shares in that chapter is that most of us assume we ask plenty of questions, but research shows we’re asking far fewer than we think. This is why some of us leave a conversation feeling deflated or less motivated to get together with that friend again. Here is the October assignment (or do it any month you’re reading this).
When you’re interested, you become interesting!Listen to episode #167 on Apple, Spotify, YouTube, and anywhere you listen to podcasts! Let me know how it goes!REMINDER: You can start the 2025 challenge any time. Each month is meant to stand alone and you don’t need an entire month to accomplish any of them. Come back and let me know how it went no matter when you try that month’s “assignment.”
Two anonymous questions you might have missed
Let’s connect outside of this newsletter: You can find me most often in the Facebook group, Dear Nina: The Group. All the social media links are below. I know I need to get rid of some them! Instagram | TikTok | YouTube | LinkedIn | My Website You’re a free subscriber to Dear Nina: Conversations About Friendship. Frustrated with some of your friends? You’re not alone! The anonymous letters are a perk for paying subscribers. You probably have a similar question. Upgrade any time for the full archive.
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Wednesday, 8 October 2025
Ask (MANY) More Questions: October Friendship Challenge
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