What should we expect from friends when we launch a new business or creative project like a book or a new company? Bestselling author Jackie Friedland joins me to wrestle with the messy feelings of disappointment, obligation, vulnerability, and gratitude that come with asking friends for support.

Jackie opens up about the rollercoaster of releasing five books—sometimes surrounded by cheering friends and other times left disappointed. We talk about planning events, the strange universe of social media “likes,” asking for reviews, and why acquaintances and strangers sometimes show up more than our closest friends and family.

If you’ve ever felt stung when friends (and family) didn’t show up for your “big thing,” or if you’ve struggled with how much to ask of the people you love, this episode will leave you feeling seen, understood, and maybe a little lighter.

 

WE DISCUSS:

• The gap between the support we hope for from close friends and the support we actually get.
• Why acquaintances and even strangers often step up more than close friends.
• How much “obligation” belongs in friendship when someone is launching a creative or entrepreneurial project.
• The delicate balance between asking for support and fearing you’re being pushy.
• Social media support: why it feels so personal when friends scroll past our posts.
• Practical ways to be direct without being demanding—what you can reasonably ask of friends, and what might be unfair.

LINKS MENTIONED:

• Jackie's newest novel is Counting Backwards
• Find Jackie on Facebook, Instagram, and on her Website
• Dear Nina: The Group on Facebook

 

MEET JACKIE FRIEDLAND:

Jacqueline Friedland is the USA Today and Amazon bestselling author of both historical and contemporary women’s fiction. A graduate of the University of Pennsylvania and NYU Law School, she practiced as a commercial litigator for as long as she could stand it. She then returned to school to earn her Masters of Fine Arts in creative writing from Sarah Lawrence College and has been writing ever since.

Jackie’s books have been awarded the 2020 and 2021 gold medals in fiction from Readers’ Favorite. Her novels have also been named the 2021 Kirkus Reviews Best Indie Book of the Year, the SheReads Best Book Club Pick of 2021, and the Women’s Fiction Writers Association Star finalist for 2022. She regularly reviews fiction for trade publications and appears at schools and other locations as a guest lecturer. Her fifth novel, Counting Backwards, was released by Harper Muse in March 2025.

Jackie lives in Westchester, New York with her husband, four children, and two dogs. You can find her on Instagram @jackiefriedland, on Facebook @JacquelineFriedlandAuthor or through her website www.jacquelinefriedland.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

My dream for "Dear Nina" has always been to make people feel less alone in the messy parts of friendship. Episode #160 was our first-ever LIVE show with 120 people in the room—and wow, you could feel the energy, see the heads nodding, and appreciate the camaraderie of an audience who has experienced the highs and lows of friend groups.

Friend groups are complicated. They can be the source of safety, belonging, and joy. But they can also be a source of exclusion, hurt, and longing. With my assistant producer and friend, Rebekah Jacobs, we dug into the messy, funny, and universal realities of friend groups from middle school cafeterias to mahj tables and even to the dining hall at the assisted living center.

Why do groups feel so good AND so painful? Do you really need one to belong? And how do you help your kids (or yourself) when a group just isn’t working? This episode has laughter, applause, and some tough-but-true advice: go where the love is.

LINKS MENTIONED:

• Dear Nina Newsletter (dearnina.substack.com)
• Facebook: Dear Nina: The Group
• Dr. Lisa Damour on Dear Nina, episode #65
• Gretchen Rubin on Dear Nina, episode #96
• My episode on Leslie Randolph's podcast, "Why Didn't They Tell Us?" episode #63: "Friendships and Fitting In"
• "Is There a Gentle Way to Drop a Friend" episode 156 of the Ask Lisa Podcast
• The final poem I read was from author Amy Weatherly of "Sister, I am With You." It can be found on their Facebook page, here. You can also hear Amy and Jess on Dear Nina, episode #86.

SPECIAL THANK YOU to our North Shore live show sponsors & partners!

🍹 @drinktwistedalchemy – cold-pressed juices at the bar

🥂 @inspirotequila – crafted the signature cocktails

🍰 @glickmanlevyresidential – sponsored the gorgeous dessert bar

👗 @enazboutique – donated 15% of sales to the National Pediatric Cancer Foundation

And thank you to these generous companies for contributing to the swag bags and/or the raffle!

@workflowsbyronna, @dr.julia.milman, @glickmanlevyresidential, @kiddlessports, @lainetoo, @maijamartinphotography, @ohhappydayconfections, @pvolvedeerfield, @get_rootz, @rosshighlandpark, @talacoffeeroasters, @enazboutique

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

As parents, we all want our kids to be kind, inclusive, and compassionate. But what about when your child simply isn’t interested in a friendship? How do you balance kindness with their right to choose who they spend time with?

This week, I revisit one of my earliest and most-loved conversations with award-winning author Jessica Speer, whose books help kids and tweens navigate the tricky terrain of friendships, including BFF or NRF (Not Really Friends)? and Middle School--Safety Goggles Advised.

This isn’t just a tween and teen conversation. It's about us as parents. Many of us have been on both sides: watching our kids be left out and watching them leave someone else out. And just like in adult friendships, chemistry matters.

Jessica shares practical language for kids to politely say “no,” stories from her own parenting experience (including a birthday party that went sideways from over-inclusion), and the importance of helping kids identify and grow healthy friendships.

If you’ve ever wondered how to raise a kind kid who also has strong boundaries without becoming the parent who micromanages every friendship, this episode is for you.

WE TACKLE:

• Teaching kids to treat others with dignity and warmth without sending the message they must be friends with everyone.
• Understanding “shared spaces” (the lunchroom or a sports team) versus private time (a sleepover or weekend hangout).
• The “romantic relationship” analogy: why we’d never force our kids to date someone they weren’t interested in, but often push friendships in that exact way.
• How to help kids gracefully decline plans without ghosting or hurting feelings unnecessarily.
• Recognizing when our own parental fears--especially about what other parents might think--are driving our actions.
• Why being overly included can backfire, and how too much forced inclusion can prevent kids from finding genuine, mutual friendships.

LINKS & RESOURCES:

• Ep #73: "I'm Just Not Into This Friendship" with guest Ruchi Koval.
• Ask an anonymous question
• "What if My Kid is the Mean One" the August anonymous question on dearnina.substack.com.

 

MEET JESSICA SPEER:

Jessica Speer is the award-winning author of books for kids and teens, including The Phone Book – Stay Safe, Be Smart, and Make the World Better with the Powerful Device in Your Hand, BFF or NRF (Not Really Friends)? A Girls Guide to Happy Friendships and Middle School – Safety Goggles Advised.

Blending social science, stories, and activities, her writing guides readers through tricky stuff that surfaces during childhood and adolescence. She holds a Master’s Degree in Social Sciences and has a knack for writing about complex topics in a way that connects with kids and teens. Jessica regularly contributes to media outlets on content related to kids, parenting, friendship, screens, and social-emotional learning. For more information, visit JessicaSpeer.com and Instagram @jessica_speer_author.

 

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

The August Friendship Challenge on Dear Nina: Conversations About Friendship is all about mixed-age friendships, and I’m grateful to dive into the topic with author Liz Alterman. Her latest novel, Claire Casey’s Had Enough, includes a beautiful friendship between a 46-year-old and a 78-year-old woman, which gave me the perfect reason to talk about why we all need a friend who’s not in our exact age and stage. August's challenge is to seriously consider having an older or younger friend in your life. (This might require a new routine or trying something other than what you're already doing week to week!)

I’ve seen the benefits of intergenerational friendships in my own life. Sometimes I’m the younger friend, sometimes the older one, and both roles come with their own gifts. Liz and I talk about what it’s like to build and nurture these relationships.

HIGHLIGHTS:

• Why mixed-age friendships can be a game changer
• How Liz’s own intergenerational friendship with author Susan Roane (of How to Work a Room fame) and poet, Melissa Elder, influenced her work and her life
• The push-and-pull of being the older or younger friend in a dynamic, and what each side uniquely brings to the table
• How to meet someone not in your age bracket (hint: try something new, say yes more often, and follow the chemistry)
• 💡My biggest takeaway from this episode? You’re not going to meet a mixed-age friend by doing the same old things. You have to get out of your comfort zone, try something new, and follow the chemistry—then be brave enough to make a move.

LINKS & RESOURCES:

• The May Friendship Challenge: The Power of Changing the Venue
• 2025 Dear Nina Friendship Challenge overview

MEET LIZ ALTERMAN:

Liz Alterman is the author of the award-winning memoir Sad Sacked and multiple thrillers. Her romcom Claire Casey's Had Enough includes an intergenerational friendship in which a forty-six-year-old and a seventy-eight-year-old inspire one another to remember the women they once were and the dreams they still hope to fulfill. Liz's essays and reported pieces have appeared in The New York Times, The Washington Post, Business Insider and more. She notes that while writing hasn't brought her fame or fortune, it's filled her life with enriching friendships that span generations. For more, visit her website and follow Liz on Instagram at @lizalterman.

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

Amy Blumenfeld was in 8th grade when she was diagnosed with Hodgkin lymphoma. While the medical story is remarkable on its own (including Amy becoming the first adolescent with Hodgkin lymphoma to have an autologous bone marrow transplant at Memorial Sloan Kettering in NYC), what stayed with her deeply was how her community showed up for her family. Just one example: a group of friends and synagogue families created a full-length skit video—Amy Night Live—to lift her spirits during isolation. Her community's love, support, and generosity became the emotional backdrop of her storytelling and work for years to come.

We talk about:

• How Amy’s real-life community inspired the fictional community and circle of friends in her debut novel The Cast
• The ripple effect of early illness on friendships, families, and even future partners, careers, and children
• How illness can reshape your view of who matters and why
• Amy's second novel, Such Good People, which explores childhood friendship and loyalty against the backdrop of the criminal justice system
• The complexities of loyalty when friends and family need you at the same time

This conversation ties closely to my upcoming Dear Nina live event in Highland Park, Illinois, which will raise money for the National Pediatric Cancer Foundation. In the introduction of the episode I mention losing my nephew Joshua McFadden to DIPG, a form of brain cancer, in 2017. A portion of ticket sales and 15% of all sales at ENAZ stores on 7/31/25 (not just in Highland Park!) will go to this important cause.

LINKS & RESOURCES:

• Joshua's story on NPCF's site
• My episode with brother-in-law (and my first podcast producer!), Dave Dluger
• Amy's books: The Cast and Such Good People

MEET AMY BLUMENFELD:

Amy Blumenfeld is an award-winning author and journalist. She is a graduate of Barnard College of Columbia University and received a master’s degree from the Columbia University School of Journalism. Her articles and essays have appeared in various publications including the New York Times, The Huffington Post, O, The Oprah Magazine, as well on the cover of People. Amy’s debut novel, The Cast, was selected as a New York Post Best Book of the Week. She has contributed to three non-fiction books, including a USA TODAY bestselling anthology. Amy lives in New York with her husband and daughter. Such Good People is her second novel. Find Amy on Instagram @AmyBlumenfeldAuthor.

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

It’s the four-year anniversary of Dear Nina: Conversations About Friendship! Whether you’ve been with me from the column that began in 2014, started with the first episode in 2021, stumbled in at episode 86, or you're new around here at #156—thank you. Thank you for caring about friendship on a deep level and for helping this podcast grow into something that’s helped me (and hopefully you) navigate the joys and messes of adult friendship.

In this solo episode, I’m marking four years of Dear Nina: Conversations About Friendship with the four major lessons I’ve learned about friendship from hosting the show—and four lessons I’ve learned about podcasting along the way.

And a special to thank you to my many fantastic guests!

🎁 Anniversary Favor 🎁

If Dear Nina has helped you in any way—big or small—please share your favorite episode with a friend or on social media. It’s the best way to keep the conversations going, and it means the world to me.

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

After 31 years on the East Coast, Lisa Giordano decided (less than a year ago) to make a big move to Austin, Texas, with zero local contacts and a personal challenge to build a community and social life from scratch. In this upbeat conversation, Lisa tells us what really works (and what does not) when you’re starting over single in a brand-new city—or simply trying to make new friends right where you've lived for years. 

WHAT WE COVER:

• Admitting you want friends: Why naming the need out loud is the best thing to do.
• DMs & daily errands: The social media message and the post-office line that sparked Lisa’s first new friendships.
• The “one-plan” weekend rule: A realistic guardrail against both isolation and social burnout.
• Why nearby beats “perfect”: How living a few miles apart can matter more than instant chemistry.
• Mixed age friendships: The benefits of friendships with people in similar life stages but different ages.
• When you don't click: Not taking things too personally is essential to moving forward and finding new potential friends.
• Solo time as a skill: Creating intentional solo time so your happiness isn’t dependent on anyone else's schedule.
• It's never too late to make new friends: I shared a story about my mom's recent 80th birthday party.

 

LINKS & RESOURCES:

• My episode on Lisa's podcast, Surthriving
• Episode #130 with Hallie Sawyer on "Sober Curiosity"
• Episode #115 on "Freshmen Energy" and making new friends as an adult
• Lisa on Instagram and TikTok

MEET LISA GIORDANO:

After living in the northeast for all of her life, Lisa took a leap of faith at the age of 31 and moved cross country to Austin, Texas, without knowing anyone. Filling her car to the brim and driving across the country with her cat, she embarked on a new journey and decided to document it along the way. Lisa is a typical single 30-something building a life she thrives in. She makes lifestyle content and documents navigating her 30s, starting over, solo life, life in Austin, and anything else that inspires her! Find her on Instagram and TikTok and on her podcast, Surthriving.

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 that low-level hum of annoyance when a friend casually drops your (good or bad) personal news into the conversation? I have my fantastic "Dear Nina" assistant producer, Rebekah Jacobs, with me this week to crack open a listener's anonymous letter about DISCRETION.

Discretion is that gray zone between gossip and harmless chatter. Rebekah and I discuss how much we can expect friends to know intuitively what stays private and what's OK to share.

We're not talking about friends who gossip incessantly about you or reveal a big secret. That's easier to answer! Keep THAT friend at arm's length.

Discretion is another category entirely and we get to the bottom of it in less than 30 minutes.

IN THIS CONVERSATION

• The blurry line between discretion and gossip
• Experiencing a friendship “tap on the shoulder vs. smack in the face”: learning from small slip-ups before they become big mess-ups
• Nina’s mom’s reminder: Not every friend is a close friend
• Practical ways to decide what you can share, what you should share, and when to hit pause
• Why “share your truth” and “protect your privacy” don’t have to be opposites
• A Jewish teaching on mindful speech that still works in the screenshot age

LINKS & RESOURCES

• Ask an anonymous question
• Eventbrite tickets to see Nina and Rebekah LIVE in Highland Park, IL: “From the Cafeteria to the Mahj Table: Friend-Group Challenges from Teens to Mid-Life and Beyond.” Tickets are going fast!
• White Lotus Friendship Trio episode with Rebekah
• Episodes with my mom as the guest if you want more of Kathy's advice.
• Episode #136 with Rebekah about finding your 3-5 closest friends. (Another letter spotlight episode)
• Episode #112 about college admissions and friendship
• A bit more information about the laws of speech in Judaism

 

MEET REBEKAH JACOBS

Rebekah has been a reading specialist and writing instructor for over 20 years, teaching in Boston, Chicago, DC, and Los Angeles. Currently, she teaches college writing in DC, and her own writing has been featured in Kveller. As assistant producer for Dear Nina, she is passionate about ideation and brainstorming creative concepts. She tries to read 80 books a year and loves TV—though, unlike Nina, cooking and tech are not her strong suit. She lives with her husband, three kids, and a golden doodle named Peanut.

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

Ready to see where your friendships stand halfway through 2025? In this solo episode, I (very quickly!) round up the first six monthly challenges. Then I hand you three laser-focused questions to help you reflect, assess, tweak, and strengthen your connections for the rest of the year. 

Answer the 3 Questions This Week!

1. Block 15 minutes.
2. Jot down honest answers. And bullet points count!

LINKS & RESOURCES

• Join the Dear Nina Facebook Community to discuss wins and struggles from all the monthly challenges.
• Previous Monthly Challenges in the newsletter (Jan–June 2025)
• Episode #127, January: See a friend in person
• #131 February: Start a friendship ritual
• #135 March: Plan a hyper-local hangout
• #140 April: Put your friends' birthdays in your calendar
• #144 May: Change the venue where you spend time with a friend or change how you communicate
• #149 June: Ask a friend for a favor
• Episode 121 about "Rules for Making Plans"

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

Facing Unfinished Friendship Business When Your Child Hits Social Snags

Your child’s social life can stir up every unresolved playground scar you’re still carrying. Licensed clinical social worker and EMDR therapist Beth Segaloff joins "Dear Nina" to talk about separating our past (and present) friendship baggage from our kids’ current experiences. We discuss how kids' realities are so different today and why that small pause before jumping in to “fix” everything is parenting gold.

HIGHLIGHTS:

• Why your kid’s friendship bumps feel personal--how to tell what feelings belong to you versus your child.
• The 2025 friendship landscape: 24/7 phones, "Snap Maps," and over-scheduled lives
• The space between reacting and responding--how a moment of silence can change the whole conversation (and other strategies for when your child is struggling with friendships).
• Why forcing invitations or calling another parent for a favor often backfires, and what true support looks like instead.
• Modeling adult friendships: intentional intimacy vs. accidental exclusion

MEET BETH SEGALOFF

Beth Segaloff is a Licensed Clinical Social Worker, EMDR therapist, yoga instructor, and Reiki healer dedicated to holistic healing and transformation. As founder of Tree of Life Center in Fairfield, CT, she offers in-person and virtual support for grief, trauma, and life transitions. Through programs like Living Fully with Grief and Life School 360, Beth empowers clients to move from pain and loss toward love, meaning, and purpose. Find Beth on Instagram at @tree.of.life.center.

 

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