Dear Nina: Conversations About Friendship

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#168 - From Surface to Substance: A Journalist’s Guide to Deeper Friendships (with Jonah Kaplan)

2025-10-1034:38

Ever feel like your friendships are trapped in the very general "how are you?" catch-up loop? Award-winning journalist Jonah Kaplan joins me to talk about moving from small talk to something more substantive that feeds connection. Jonah has spent two decades covering difficult stories for CBS and WCCO, and he’s learned that the best conversations—on camera or off—come from curiosity, empathy, and follow-up questions that go beyond the obvious.In a world of quick texts, busy schedules, and constant scrolling, it’s easy to keep friendships at the surface level. But the friendships that truly sustain us are the ones with depth. Related to the October friendship challenge for Dear Nina listeners, Jonah is an excellent guide for asking questions that bring conversations to another level.WE COVER:How to reframe small talk (try “What surprised you most about your trip?” instead of “How was it?”)Creating connection through conversation: don’t wait for invitations—initiateReading the room so vulnerability feels safe, not forcedWhy men need deeper conversations, tooHow honest conflict can make a friendship strongerThe power of mixed-age friendships to keep you growingWhat friendship and journalism have in commonMEET JONAH KAPLAN:Jonah Kaplan is an award-winning journalist (and the son of two rabbis!) who has built a strong reputation for his balanced reporting, thoughtful interviews, and deeply researched coverage of high-impact issues affecting the community. His work appears on all of WCCO's newscasts and is often featured on CBS News' programs and platforms, including the CBS Evening News, CBS Mornings and CBS 24/7. (See Jonah's full bio at cbsnews.com/team/jonah-kaplan/). Find him on Facebook or on 'X' at @JonahPKaplan.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. Special thank you, as always, to my assistant producer, Rebekah Jacobs!

#211 - You Don’t Have to Be Fully Secure to Have Good Friendships (Dr. Marisa G. Franco)

2026-09-1437:01

Dr. Marisa G. Franco returns to talk about her new book, Worth, and how self-worth shapes the way we experience friendship. We discuss why old rejection can follow us into new relationships, how insecurity can affect reciprocity and reassurance, and why our assumptions about what friends think of us aren’t always accurate. Marisa also explains why the goal isn’t to become perfectly secure—it’s to become “secure-ish.” Special thank you, as always, to my assistant producer, Rebekah Jacobs!

#210 - AI, Friendship, and the Danger of Outsourcing Connection (Sarah Baldeo)

2026-09-0644:27

What happens when AI starts to feel less like a tool and more like a friend? I spoke with neuroscientist and AI futurist Sarah Baldeo about outsourcing empathy and emotional processing, why real relationships require friction and disagreement, and what concerns her most about teenagers growing up with generative AI. Sarah has spent more than 20 years working at the intersection of neuroscience and artificial intelligence, so I wanted to bring some of my biggest worries about AI and human connection directly to her and I appreciated her treating my concerns with seriousness and respect. Special thank you, as always, to my assistant producer, Rebekah Jacobs!

#209 - Friendship Skills for Neurodivergent Kids and Adults (Caroline Maguire)

2026-08-3050:09

Friendship expert Caroline Maguire joins me to talk about friendship skills for neurodivergent kids and adults. We discuss encouraging connection without forcing it, handling rejection, understanding the difference between acquaintances and friends, and finding environments where friendship can grow more naturally. Most of all, Caroline makes the case that building friendship skills doesn’t mean becoming someone else—it means finding the people who appreciate you as you are. Special thank you, as always, to my assistant producer, Rebekah Jacobs!

#208 - Making Friends at Any Age Takes a Little Risk (Harlan Cohen)

2026-08-2342:15

Making friends at any age requires some willingness to put yourself out there—and to accept that not every invitation, effort, or friendship will go the way you hoped. New York Times bestselling author Harlan Cohen joins me to talk about finding your people, taking social risks, and his framework of “people, places, and patience.” We also discuss what to do when you’re always the one initiating plans, the difference between expectations and requirements in friendship, and why we all need places where we can simply show up as ourselves. Harlan works extensively with college students and parents, but this conversation is truly for anyone trying to make, deepen, or better understand friendships at any age. Special thank you, as always, to my assistant producer, Rebekah Jacobs!

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Dear Nina: Conversations About Friendship