The Real Work Behind Lifelong Friendship

This week I’m joined by two women who accidentally went viral on social media, but they've been doing the real work of close friendship for over four decades. I'm a BIG fan and begged them to let me examine their friendship on the show. Meet Jenn Sherman (who you might know from Peloton) and Pam “Sunny” Sunshine who are the best friends behind the popular @sunnyandjenn accounts on TikTok and Instagram.

Jenn and Pam's story is fun (truly wild TikTok origin included), but the real gold is how they’ve stayed close through many stages of life—college, moves, careers, parenting, vacations, losses, and now a shared business.

If you’ve ever wondered why some friendships last and others quietly fade, this episode is packed with answers you can use with old friends and new friends alike.

HIGHLIGHTS FROM OUR CONVERSATION:

• Why “luck” isn’t enough for close friendship — The role of effort, showing up, and consistency.
• Proximity matters — How living close (or “close enough”) keeps friendships alive. When making NEW friends, keep this in mind! 
• Scheduling is everything — Coffee dates, beach days, girls’ trips: it's all about the calendar.
• The 200-hour rule — How friendships actually deepen over accumulated time.
• Cheering, not competing — Celebrating your friends' wins without jealousy.
• Handling conflict early — Sunny’s “lumpy rug” rule and why resentment ruins trust. Plus some other great "Sunnyisms."
• New friends later in life — Why it’s never too late for a deep connection.
• The viral TikTok moment — How a random street interview changed everything and a business was born.

LINKS MENTIONED:

• Follow @sunnyandjenn on TikTok and Instagram 
• Jenn on Peloton (if you’re a rider, you already know)
• Lindsay Pinchuk's Dear FoundHer community 
• Sunny & Jenn's live show! Tickets for the December show in Aventura, Florida are here. 
• The Beaches episode of Dear Nina where two psychology professors join me and producer, Rebekah Jacobs, to analyze CC Bloom and Hillary Whitney's friendship.

MEET JENN SHERMAN AND PAM SUNSHINE:

Sunny and Jenn are lifelong best friends turned content creators, sharing their journey with audiences on Instagram and TikTok. Friends for more than 40 years, they bring humor, honesty, and heart to everything they do — from wellness and midlife shifts to the everyday moments of friendship. Their platforms celebrate living authentically, laughing often, and reminding people that the best parts of life are meant to be shared.

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

You've arrived at the best academic nerd-out ever on the movie Beaches. Find out why CC Bloom and Hillary Whitney's instant friendship chemistry, breakups and makeups, and tear-jerker ending still wrecks us (in the best way). Is there something we can still learn in 2025 about making, keeping, and losing friends from this late 80s film? Absolutely. And professors of psychology agree!

My assistant producer, Rebekah Jacobs, and I were thrilled to dissect Beaches and its timeless lessons on friendship with psychology professors Paul Eastwick of UC Davis and Eli Finkel of Northwestern University. Paul and Eli are also the dream team behind the Love Factually podcast, where they explain what our favorite romantic films get right--and wrong--about the science of romance. For this episode of Dear Nina, they turned that laser focus to friendship instead. 

We examined CC & Hillary's iconic bond through research on conflict, jealousy, apologies, complementary roles, the “soulmate” mindset, and more. We laughed a lot too! 

Yes, we quote the department store fight. Yes, we talk about "Wind Beneath My Wings" and other unforgettable songs from the film. Yes, Rebekah wore a Bette + Barbara t-shirt. It’s peak friendship content with genuine lessons for your adult friendships. Don't miss this one! 

HIGHLIGHTS:

• What Beaches gets right about how close friends actually operate.
• Why the first apology flopped, what finally worked, and how to apologize like a grown-up.
• The “best friend” myth, challenged: You don’t need a single ride-or-die to have a rich friendship life.
• Do opposites attract? That's not backed by relationship science, but roles do emerge in most relationships.
• Why “I’ll hire a nurse” isn’t the same as “I’ll take care of you,” and how responsiveness deepens bonds.
• Anger is often a mask for hurt; naming the deeper feeling opens the door to repair.
• Forgiveness lands when both people agree a “debt” exists. 
• Your romantic partner as your "best friend" might not be the best idea. 
• How your beliefs about soulmates influences they way you're willing to work things out (or not).
• "Transformation of motivation" was a new term to Rebekah and to me, and we loved it. You'll have to listen to learn more!

 

LINKS MENTIONED:

• The Love Factually podcast, hosted by Paul and Eli
• The White Lotus/Dear Nina episode where Nina and Rebekah discuss the friendship trio
• Listen to the Beaches soundtrack on Spotify

 

MEET THE PROFESSORS:

Eli Finkel is a Professor of Psychology and Management at Northwestern University. He is the author of The All-Or-Nothing Marriage: How the Best Marriages Work, the founding co-director of the Litowitz Center for Enlightened Disagreement, and the co-host of the Love Factually podcast.

Paul Eastwick is a Professor of Psychology at UC Davis and author of the forthcoming book Bonded by Evolution. His research and writing has been featured in outlets like The New York Times, The Atlantic, NPR, and Scientific American Mind, and he is a co-host of Love Factually

MEET REBEKAH JACOBS:

Rebekah Jacobs is the assistant producer of Dear Nina: Conversations About Friendship and a writing professor who lives in Bethesda, Maryland, with her husband and three kids. 

 

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

This month’s friendship challenge is all about generosity, but not the kind that empties your wallet or the type that requires a special occasion like a birthday or holiday gift. Think thoughtfulness and the joy of letting friends know you're thinking of them for no reason whatsoever. It's generosity of time and spirit merely to show friends they matter to you.

A small gesture can leave a big impact. In this short episode, I share a few stories of simple, meaningful gestures from friends that have stayed with me for years. Some of those gestures were in the form of an expected gift (like a novel or cookbook) and others were simply an offer to be there on an emotional day, sending a “this made me think of you” text, or sharing a photo or meme that made me smile. All the examples inspired me to do the same over the years.

Doing something unexpected for a friend is the easiest challenge yet. Well, maybe writing your friends' birthdays in your calendar for April was even easier, but this one is up there.

Whether you’re gifting a cookbook, sharing a poem, or sending a funny meme, this challenge is about reminding your friends that you’re thinking of them, not because you have to, but because you want to.

AND, make sure to visit me and fellow Dear Nina listeners in the Facebook Group or on my Substack newsletter to let us know what you did or plan to do. Let's share ideas!

As always, if this episode made you smile or inspired you, share it with a friend, leave a review, or post it to your story. That small act of generosity fits the challenge perfectly. :)

MENTIONED IN THIS EPISODE:

• Find all previous Dear Nina Friendship Challenges here. 
• Episode 170: "The Friend Who Really Sees You." This was my conversation with poet Hannah Rosenberg about friendship and her book Same
• Cookbooks mentioned: Robyn sent Peas, Love, & Carrots. Julie sent Vegan At Times.
• Find me at the Dear Nina Facebook group to report on what you did this month to bring some joy to a friend!

 

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

"This made me think of you." Is there anything more delightful to hear from a friend? These are the words often written between friends when someone shares one of Hannah Rosenberg's (always viral!) poems from Instagram. And the incredible Hannah Rosenberg is my guest on Dear Nina. I was so excited to meet the woman behind the words I've been sharing in my own Instagram stories for years. 

Hannah is the author of the poetry collection, Same, from St. Martin's Press, and her work about friendship, motherhood, and everyday life has made thousands of people online say or write “same” in the comments or when they share her work.

Together Hannah and I dive into what it actually means to feel seen, and how to make your friends feel seen. Hannah reads some of her most-shared friendship poems. There are tears (the good kind). And it’s a warm, genuine conversation about connection, vulnerability, and the friendships that quietly save us.

Topics we cover:

• The meaning behind “Same” and how it became a viral poetry movement
• Why adult friendship deserves real rituals and recognition
• How to bridge distance and stay close when life changes
• The difference between being comforting and being dismissive
• Friendship poems that say what we all feel but can’t quite express

Poems & passages mentioned

• “When I Needed My Friends” 
• “Group Text”
• “Home (for Katie)”  
• “Marriage of Friends” 

MEET HANNAH ROSENBERG:

Hannah Rosenberg is a poet whose work has been shared widely online, and she has been featured in publications serving women and parents like Darling and In Kind. She lives in the greater Philadelphia area with her husband and daughter, who often find themselves as the subjects of her poems. You can find her work on Instagram @hannahrowrites. Learn more at hannahrowrites.com

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

Want a social gathering for making new friends or deepening friendships that’s not a book club, not mahjong, not a cooking club, not pickleball—just high-level, soul-filling conversation? Enter "the salon."

Linda-Marie Barrett, author of Creating a Salon: The Magic of Conversations that Matter, shows us exactly how to plan a modern salon: who to invite (and who not to), how to set a clear purpose, what to do about dominant talkers, and why ending well matters as much as beginning well.

If this episode nudges you to start a salon, tell me how it goes. What did you try? What surprised you? What will you tweak next time? All the ways to find me are in the link below.

What we cover

• What a salon is (and isn’t): an intentional, guided conversation on a theme
• Why salons help friendship: they deepen bonds and create new ones by giving everyone structured airtime.
• Hosting with with authority and kindness: Linda-Marie and I talk timers, bells, and how to intervene when someone is taking over to make sure everyone in the group has a chance to participate.
• Designing the experience: purpose, people, place, ground rules, accessibility, potluck flow, parking and a thoughtful way close the evening.
• Trouble spots: late arrivals, phones on the table, oversharing, and the art of the one-on-one follow-up.
• A complete sample format of a salon you can lift for your first salon.

MEET LINDA-MARIE BARRETT:

Linda-Marie Barrett is a writer, editor, and executive director of the Southern Independent Booksellers Alliance (SIBA). Before that, she was at Malaprop’s Bookstore/Cafe, where she wore many hats, including events manager and founder and host of a book club that continues today, Women In Lively Discussion or WILD. She has been hosting her Black Swan Salon since 2017 and has no plans to ever stop. She lives with her husband, writer and blogger Jon Mayes, in Asheville, North Carolina. Find her on Facebook and Instagram. 

 

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

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.

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

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

A good apology can save a friendship; a bad one can torch it. And yes, our friends will mess up. As will we! That's why learning to say "I'm sorry" (and why!), accept an apology, and even ask for a better apology if the one you got was "off" are all important skills in maintaining and deepening your friendships.

In this episode of Dear Nina, I spoke to author and journalist Marjorie Ingall, co-author with Susan McCarthy of Sorry, Sorry, Sorry: The Case for Good Apologies (released in paperback as Getting to Sorry: The Art of Apology at Work and at Home) and co-creator of SorryWatch.com.

Marjorie walks us through the six essential steps of a good apology and the “half step” people often forget. We discussed why bad apologies are worse than none at all, and how the timing of an apology can make or break it. Whether you’re struggling to say sorry, waiting for an apology that may never come, or wondering how to truly forgive, this conversation offers practical tools you can bring into your friendships right away.

We also explore:

• The difference between guilt and shame, and how each affects friendships.
• Why accepting an apology can be just as challenging—and important—as giving one.
• When it’s okay (and even healthy) to ask for an apology you feel you’re owed.
• Why rushing to apologize can actually backfire.
• The power of letters—both to give an apology and to solicit one.
• How forgiveness (when possible) benefits not just the friendship, but your own health and peace of mind.
• We also touch on the Jewish High Holidays as a time of reflection and repair, how apologies evolve as we age, and what Marjorie's favorite children’s book, A Bargain for Frances, can teach all of us about navigating imperfect friendships.

 

LINKS AND RESOURCES: 

• The ten days between Rosh Hashanah and Yom Kippur
• Ep. #34 of Dear Nina: Reconnecting with an Ex-Friend
• The six steps of a good apology on sorrywatch.com
• "Waiting for an Apology That Will Never Come" (Nina's 2014 article on Kveller)
• A Bargain for Frances by Russell Hoban

MEET MARJORIE INGALL

Marjorie Ingall is the co-author, with Susan McCarthy, of Sorry, Sorry, Sorry: The Case for Good Apologies (released in paperback as Getting To Sorry) and co-creator of the apology watchdog site SorryWatch.com. She’s also the author of Mamaleh Knows Best: What Jewish Mothers Do to Raise Successful, Creative, Empathetic, Independent Children. She often writes about children’s books for the New York Times Book Review and has written for many other magazines and newspapers, including Tablet and The Forward — she was a columnist for both — as well as Town & Country, Glamour, Self, Ms., Elle, New York, Time, and Newsweek. Back in the day, she was the senior writer and books editor at the late, lamented Sassy Magazine. Find Marjorie on Facebook and Bluesky.

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

Different choices, same friendships—if you’re willing to speak up.

This week on Dear Nina: Conversations About Friendship, I talk with bestselling author Dani Alpert, who has always known she didn’t want children. While her five best friends all married and had kids, Dani carved out a different life. The result? Decades of navigating friendships where communication was extra necessary to keep resentment and misunderstanding at bay. Dani says it took a lot work, but she did not want to lose these important relationships and every hard discussion with close friends was worth the effort.

Dani has advice for listeners that goes beyond whether you have kids or not. Many areas of life and the decisions we make can set us apart from the path our friends chose. No matter the "topic," communication and honesty is key. There's no other way to hold onto the friendships that matter to you. Whatever the difference is between you and your friends, Dani’s wisdom applies: speak up, be honest, and trust that the right friends will stick.

Listen to my conversation with Dani for a funny, candid, and deeply relatable episode about friendship across different life paths.

HIGHLIGHTS:

• The resentment that can build when your life path looks different from your friends’ choices
• Why it’s so important to actually say the uncomfortable things out loud to friends
• How true friends will hear you, even if your words come out messy
• The loneliness that can creep in when “everybody” seems to be living a life you didn’t choose. For Dani the example is being child-free by choice, but this can apply to so many paths.
• Why naming your needs sooner (but also knowing it’s never too late) can save a friendship
• We also squeezed in a quick few minutes and doing art (writing, etc.) because you're passionate about it, not because you're expecting a certain outcome in sales or attention.

MEET DANI ALPERT:

Dani Alpert is the best-selling author of Hello? Who Is This? Margaret?—a new collection of humorous essays—and the memoir, The Girlfriend Mom, winner of the 2020 Story Circle Network Gilda Award for comedy, honoring Gilda Radner. Her work appears in numerous outlets. Dani spent decades working in theater, television, and film, performing, writing, and directing. She’s a Pilates instructress and advocate for the Down syndrome community. Dani’s first headshot was her mugshot taken after being arrested for tagging when she was a juvenile. She’s been trying to reclaim those glory days ever since.

 

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

New parenthood can be isolating and full of unspoken (or spoken!) pressures. But those early years are not only about the challenges. There are opportunities too! For one, being at a drastically new stage of life is a common time for making friends who are going through similar experiences. I spoke to Alex Reed, a new-ish mom (at least compared to me--a mom for two decades), a tech-industry pro, and the creator behind Roses & Radicchio, an Instagram account and newsletter that celebrates connections that make life meaningful.

Alex and I discussed:

• Practical ways to meet other moms
• Why community is one of the most protective things for perinatal and postpartum mental health
• Staying part of a community matters, even if your close friends do not come from these groups and activities. Acquaintances can become friends, connectors, or lifelines later (school, camps, emergencies).
• Using small, low-cost asks when you spot a potential new mom friend: “I’m going to the park tomorrow, want to join?” Short time windows might feel more doable.
• How to spot a new-mom-friend judgement issue early and stop the comparison cycle
• Accepting different parenting and new-parent socializing styles (turning outward for a bigger network vs turning inward to a small circle)
• The importance of keeping connections with friends who do not have kids
• Remembering social media can amplify shame and false “shoulds”
• AND NOTE: If you’re struggling, community helps but professional support is so important. If you’re worried about postpartum depression or anxiety, seek help.

This isn’t a “you must do X” to make new mom friends conversation. This is all about advice and empathy for a potentially lonely season of life.

 

LINKS & RESOURCES:

• Roses & Radicchio--Alex's Instagram account and newsletter
• A few other parenting episodes on DEAR NINA (mostly aimed at parents with teens): #2. When Your Friend’s Kid is Being Mean to Your Kid; #59. Difficult Teen Friendships & Parent Involvement; #86. Every Friendship Starts With an Act of Bravery; #91. Helping Kids Manage Conflict With Friends; #59. Teaching Kindness Without Forcing Friendships
• Modern Friendship by Anna Goldfarb is a book Alex and I both loved. Anna was also featured on several episodes of Dear Nina, most recently #126.
• "The Search for the Perfect Stroller is Really a Search for Control" (I first had this published in Brain, Child Magazine in 2015 and later re-published in Scary Mommy in 2021.)
• The Peanut app

 

MEET ALEX REED:

Alex is a gathering enthusiast, photographer, tech professional, and toddler mom who brings creativity and connection into everyday life. Outside her day job at a Fortune 50, she runs Roses & Radicchio, a lifestyle Instagram and Substack where she shares approachable tips for elevated entertaining, vintage treasure hunts, food and flower creations, and current reads. Passionate about conversations around adult female friendships, Alex uses her platform to celebrate the connections that make life meaningful. She lives in Northern Virginia, just outside Washington, D.C., with her husband, energetic toddler, and their allergy-prone French bulldog.

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