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—initiate
• Reading the room so vulnerability feels safe, not forced
• Why men need deeper conversations, too
• How honest conflict can make a friendship stronger
• The power of mixed-age friendships to keep you growing
• What friendship and journalism have in common

MEET 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.

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Thank you to this week's sponsor: SINCERENOTES. SincereNotes is available to download free on Google Play and App store.

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