Welcome to the Dear Nina Friendship Challenge for June: Ask a friend for a favor.

Why? Asking a friend for a favor demonstrates trust and intimacy. It helps your friend feel closer to you merely because you asked, and this will strengthen the friendship. Unfortunately, people really struggle asking for help, even for the smallest of favors. This month I want you to practice this important skill!

I also ask you to consider if you struggle asking friends for help because you're afraid people will then ask you for help. That's how friendship works! We have to be inconvenienced sometimes for friends and community, which is good for relationships AND for society.

I packed a lot into a 12-minute episode. I hope you'll join me in the June Dear Nina Friendship Challenge.

LINKS & RESOURCES

• Join the Dear Nina Facebook Community to discuss wins and struggles from all the monthly challenges.
• Previous Monthly Challenges (Jan–May 2025) are all linked at dearnina.substack.com.
• The episode I mentioned with Gretchen Rubin

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.

THIS WEEK'S SPONSOR: Download Slowly to make a genuine friendship today. It’s free on the App Store and Google Play.
Download link: https://open.slowly.app/miXL/54lnblyi

I sat down with fifth-generation etiquette expert Daniel Post Senning of The Emily Post Institute to explore how classic (and modern!) manners can strengthen and even rescue our adult friendships. We discussed using etiquette for group chat issues, RSVP blunders, office friendship confusion, misuse of AI, bringing up kids' cringe posts, cocktail party escapes, staying friends when your kids' friendship falters, and friendship breakups.

You don't want to miss this one!

LINKS & RESOURCES

• Emily Post's Business Etiquette is the newest book from Dan and Lizzie
• The Emily Post Institute on Instagram
• Dan and Lizzie's podcast, Awesome Etiquette
• We referred to one of my earliest episodes! #2 "When Your Friend's Kid is Being Mean to Your Kid"

MEET DANIEL POST SENNING:

Daniel Post Senning, great-great-grandson of Emily Post, is co-president with his cousin, Lizzie Post, at the Emily Post Institute. He manages the company’s training programs, has authored and co-authored many books on etiquette, covering topics from business to digital manners, and delivers seminars and speeches on these topics around the world. An active spokesperson for the Institute, he regularly speaks with media outlets about business, technology, and dining etiquette. Daniel has appeared on The Today Show, The History Channel, and ESPN, and has been interviewed by publications including the New York Times, GQ, Time Magazine, and the Wall Street Journal. He most enjoys answering questions as a co-host on the Institute’s weekly podcast, Awesome Etiquette, from his home in Duxbury, Vermont, where he lives with his wife, Puja, and their children, Anisha, Arya, and William.

 

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.

THIS WEEK'S SPONSOR: Download Slowly to make a genuine friendship today. It’s free on the App Store and Google Play.
Download link: https://open.slowly.app/miXL/54lnblyi

In this short solo episode, I consider why some people hesitate to tell friends about positive events like a promotion, a published piece, or a personal milestone or achievement. Likely due to cultural conditioning, we worry it will come off as bragging. I think it's a missed opportunity to feel closer to friends when all good news is kept under wraps.

Not sharing can also have a cost. When friends learn about our news secondhand, it can create distance and misunderstandings.

Vulnerability is a key to closeness, and sharing GOOD news is an excellent way to make yourself vulnerable.

Equally as important in this episode: I discuss receiving your friends' good news with graciousness, curiosity, and shared joy if you want friends to keep you in the loop. When a friend shares something exciting, offer clear enthusiasm and ask a follow-up question!

LINKS AND RESOURCES

• Hear me on NPR Life Kit: "How to Keep Old Friends" Apple. Spotify.
• Join the Conversation: In the Dear Nina Facebook group we swap friendship wins and dilemmas.
• Episode 146 of Dear Nina on not overthinking in your friendships and tolerating uncertainty.

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.

THIS WEEK'S SPONSOR: Download Slowly to make a genuine friendship today. It’s free on the App Store and Google Play.
Download link: https://open.slowly.app/miXL/54lnblyi

If you’ve ever reread a text 10 times, filled in every silence with worst-case scenarios, or found yourself leaving too many hangouts with friends regretting what you said, this conversation is for you. Psychologist Dr. Jackie Henry and I discuss tools to stop overthinking your every friendship move and learn to tolerate uncertainty in your relationships. We rarely know what someone else is thinking, and we need to stop assuming we do. Wouldn't it be refreshing to just be in your friendships and not feel like you're "performing" to always say and do the exact "right" thing? Dr. Jackie offers Dear Nina listeners practical tips for getting out of your head and back into your life so your friendships can thrive.

KEY TAKEAWAYS

• Silence usually means “busy,” not “they secretly hate me.”
• Budget your “energy bucks.” Rumination is a waste of energy; spend wisely.
• Constant overthinking can create distance between friends and lead to miscommunication, anxiety, and the fear of judgment.
• Work to tolerate the unknown: there's power in letting things unfold naturally in friendships.
• Lead with curiosity. A simple “Hey, when’s good to chat?” beats the story your telling yourself about why someone hasn't responded.

LINKS & RESOURCES

• Dr. Jackie Henry’s Substack: Less Thinking, More Living
• The Dear Nina monthly friendship challenges. (The April one was mentioned in this episode.)
• The TikTok account I mentioned about recounting awkward moments. @amymaurercreel

 

MEET DR. JACKIE

Dr. Jackie Henry is a psychologist, writer, and founder of Less Thinking, More Living—a platform dedicated to helping people stop overthinking and start fully embracing life. Based in the Twin Cities, she also works as a wellness consultant and has a private therapy practice. Dr. Jackie combines humor, heart, and relatable insights to help individuals navigate life with greater ease and presence. Outside of work, she's at the cabin, playing board games, or enjoying happy hour with her husband, four daughters, and their small but mighty dog. You can find her on Instagram @dr.jackiehenry or on Substack at Less Thinking, More Living.

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.

THIS WEEK'S SPONSOR: Download Slowly to make a genuine friendship today. It’s free on the App Store and Google Play.
Download link: https://open.slowly.app/miXL/54lnblyi

Meghan Keane, author of Party of One: Be Your Own Best Life Partner, says one of the top complaints single people have about their married friends is that they feel like a problem to be solved. Another is that their dating lives are the sole focus of a married friend’s attention. Meghan joins me to unpack “singlism,” the subtle (and not-so-subtle) ways society sidelines single adults. We discuss concrete steps couples can use to include their single friends, the reality of friendship after life transitions, and good basic social kindnesses everyone can use for ALL of their friendships. Whether you’re partnered or single, this conversation will sharpen your friendship skills and remind you that friends like to be asked about all aspects of their lives (not just their dating lives, their "mom life," their careers, and so on).

HIGHLIGHTS

• How singlism, a term coined by Dr. Bella DePaulo, is often based in myths and harmful stereotypes
• Why singleness isn't something to be solved by a partnered friends
• Rules for married/partners friends when it comes to their single friends (don't treat dating life as entertainment, help with mundane life tasks, celebrate accomplishments, hang out one on one, include in larger plans).
• Why working through conflict is a sign of a deep friendship
• What married people can learn from single people about maintaining strong social ties

LINKS & RESOURCES

• Meghan's book, Party of One: Be Your Own Best Life Partner
• Find Meghan on Instagram @damekeane
• We referred to previous Dear Nina episodes with Dr. Marisa Franco, Gretchen Rubin, and Ruchi Koval

MEET MEGHAN KEANE

Meghan Keane is the founder and supervising editor for NPR's Life Kit, which brings listeners advice and actionable information about personal finances, health, parenting, relationships and more. She is responsible for the editorial vision of Life Kit, which aims to serve NPR's larger mission of public service. Prior to founding Life Kit, Keane was a producer for NPR's award winning podcast Invisibilia. There, she produced long form stories about understanding human behavior and the invisible forces that shape our lives. She reported stories about the intersection of positivity, grief, and Disneyland and another story about a woman obsessed with her daydream world. Keane is also a founding producer of NPR's TED Radio Hour, which has consistently been one of NPR's top podcasts since its debut. Keane holds a B.S. journalism degree from Emerson College and is a native of the Washington, D.C. area.

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.

 

🙏 Support the Show:

Love what you’re hearing? Share this episode with a friend or leave a review on Apple Podcasts or Spotify. Every bit helps us bring more meaningful conversations your way.

THIS WEEK'S SPONSOR: Download Slowly to make a genuine friendship today. It’s free on the App Store and Google Play.
Download link: https://open.slowly.app/miXL/54lnblyi

Whether you’re hoping to upgrade a casual acquaintance, breathe life into a longstanding friendship, or accommodate a friend whose season of life recently shifted, a venue swap can work magic without big declarations or heavy planning.

Welcome to the Dear Nina Friendship Challenge for May: Pick a newer friend or an old friend you'd like to feel closer to and initiate a change in where (or how) you hang out.

Do you normally text, but never talk on the phone? Try a call! Do you walk once in awhile, but never go out for lunch? Suggest a new restaurant in town.

I provide more ideas in the episode PLUS all the reasons why a venue change is so powerful for deepening new friendships and revitalizing old ones.

Ready to try this powerful friendship "upgrade?" Hit play, choose your venue swap, and let me know how it goes!

LINKS & RESOURCES

• Join the Dear Nina Facebook Community to discuss wins and struggles from all the monthly challenges.
• Previous Monthly Challenges (Jan–Apr 2025) are all linked at dearnina.substack.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.

 

🙏 Support the Show:

Love what you’re hearing? Share this episode with a friend or leave a review on Apple Podcasts or Spotify. Every bit helps us bring more meaningful conversations your way.

THIS WEEK'S SPONSOR: Download Slowly to make a genuine friendship today. It’s free on the App Store and Google Play.
Download link: https://open.slowly.app/miXL/54lnblyi

In this powerful episode of Dear Nina, I am joined by bestselling author Harlan Cohen to explore the truth about rejection, risk, and the myths we carry into adulthood about what friendship “should” look like. We dive into the Law of Rejection—a concept that can radically shift how you approach your relationships. Whether you're 18 or 88, accepting that we cannot control how others respond to our desire for friendship will serve you well. Friendship requires some risks, and knowing that rejection comes with the territory will allow you to take those risks.

Whether you're always the planner, the first to text, or the one who feels left out of the group chat, this conversation will reframe your perspective and give you permission to stop taking every unmet friendship expectation so personally. Plus, you will love Harlan if you've never heard him before. He's the best, and he provided me a needed wake-up call around my own fears of rejection.

TOPICS WE COVERED:

• Flipping our fears of being left out or let down in friendships into something more empowering
• How to stop testing your friends and start communicating
• Harlan's “people, places, patience” formula for building connection
• Why putting yourself in “low-barrier” places is a lifelong strategy for connection
• The pressure we put on friends and ourselves to meet unspoken expectations
• What to do if you're always the one initiating plans
• Harlan's full-circle roommate story that will make you smile and remind you that we never know what the other person in our "friendship narrative" is really thinking

 

LINKS & RESOURCES:

• Harlan’s College Success Coaching Program Best First Year
• Harlan's episode with his freshman year roommate
• You will love Harlan on Instagram and TikTok and YouTube!

MEET HARLAN COHEN: Harlan is the New York Times bestselling author of The Naked Roommate: And 107 Other Issues You Might Run Into In College and six other titles (over 1 million copies in print). His social media accounts have over 1.5 million followers and he hosts a popular podcast. He is the founder of Best First Year, a college success coaching program for students and parents. Harlan lives in Chicago, Illinois with his wife and three children.

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.

 

🙏 Support the Show:

Love what you’re hearing? Share this episode with a friend or leave a review on Apple Podcasts or Spotify. Every bit helps us bring more meaningful conversations your way.

THIS WEEK'S SPONSOR: Download Slowly to make a genuine friendship today. It’s free on the App Store and Google Play.
Download link: https://open.slowly.app/miXL/54lnblyi

What happens to our friendships when our phones are always within reach for us to "quickly check something" or "quickly answer a text?" It’s time to be honest about how available we are to everyone else while spending time with friends and how these distractions are harming our friendships. (I include myself in "we!") Is anyone else experiencing smart phone fatigue?

I spoke with author, Katherine Martinko, whose book Childhood Unplugged and Substack newsletter, The Analog Family, focuses on how to take back our presence, one small shift at a time. This episode isn’t an anti-tech rant—it’s a nuanced conversation about building a life and fostering friendships offline with intentionality. We explore what’s lost when we let phones dominate our social time and what’s gained when we reclaim our attention and presence. All issues I need as much help with as anyone else!

TOPICS WE COVERED:

• Screen time isn't just a kid issue—it's an adult problem, too
• Why undivided attention is one of the most generous gifts in friendship
• Building a richer, more soul-nourishing life offline is the key to putting your phone down more often.
• Practical tips for reducing phone use during social gatherings
• Small changes that make a huge difference
• Why 7 minutes into a conversation might be the tipping point for going deeper (if you don’t pick up your phone!)
• What it really takes to “fix your analog life first”

LINKS & RESOURCES:

• One of my favorite essays by Katherine: “Fix Your Analog Life First: It's a Prerequisite for Curbing Screen Time”
• Jonathan Haidt’s The Anxious Generation
• Cal Newport’s work on digital minimalism and deep work
• Sherry Turkle’s Alone Together
• Erin Loechner’s The Opt-Out Family

 

MEET KATHERINE MARTINKO: Katherine is a writer, editor, and speaker. She is the author of Childhood Unplugged: Practical Advice to Get Kids Off Screens and Find Balance (2023) and creator of a fast-growing Substack newsletter called The Analog Family. Katherine is a speaker on behalf of Jonathan Haidt's Anxious Generation campaign. She is a regular contributor to the Globe and Mail, Canada’s largest newspaper, and appears regularly on national radio, TV, talk shows, and podcasts, including CBC The National and Global TV. Katherine lives with her family in Ontario, Canada. See her website here.

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.

 

🙏 Support the Show:

Love what you’re hearing? Share this episode with a friend or leave a review on Apple Podcasts or Spotify. Every bit helps us bring more meaningful conversations your way.

THIS WEEK'S SPONSOR: Download Slowly to make a genuine friendship today. It’s free on the App Store and Google Play.
Download link: https://open.slowly.app/miXL/54lnblyi

It's a very special episode of Dear Nina: Conversations About Friendship dedicated to the much-discussed and debated friendship triangle in White Lotus Season 3 created by Mike White.

The friendship trio of Jaclyn, Kate, and Laurie has captivated TV viewers for the last two months. Similarly, Rebekah Jacobs (Dear Nina's assistant producer) and I have been texting and talking between episodes. Now that the season finale has aired, we shared all the lessons we think Jaclyn, Kate, and Laurie imparted on the world. Even their mistakes gave us plenty of friendship advice to ponder.

A big point that Rebekah and I agree on: Not all friendship triangles are bad! YES, even this particular trio has us defending friendship triangles. No friendship "shape" is good or bad. How individuals behave creates healthy or unhealthy friendships!

WHITE LOTUS INSPIRED FRIENDSHIP ADVICE WE DISCUSSED:

• Think carefully before sharing information with a friend. (Kate telling Laurie about Valentin)
• Be vulnerable sooner than you think. (Laurie didn't have to wait until the last night of the trip.)
• Be direct, not passive-aggressive. And don't assume friends can read your mind.
• Apologize and accept apologies when they're genuine
• Friends don't always have to be on the same page about everything
• Give your friends grace to mess up/ let some things go 
• Friends are not necessarily mirrors of each other
• Allow friends to change and grow
• Know the difference between gossip vs. genuine care and concern
• Give old friendships some of the fun, ease, and benefit of the doubt we give fresh, new friendships (Chelsea/Chloe vs. the trio of old friends)
• Don't a friend to meet every need
• Truth daggers hurt. You can be honest with your friends without being cruel.

LINKS MENTIONED IN THE EPISODE:

• You're the Only One I Can Tell by Deborah Tannen
• Episode 136: Your 3-5 Closest Friends

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.

 

THIS WEEK'S SPONSOR: Download Slowly to make a genuine friendship today. It’s free on the App Store and Google Play.
Download link: https://open.slowly.app/miXL/54lnblyi

The Dear Nina Friendship Challenge for April is about the sometimes tricky topic of friends' birthdays. The challenge itself is simple and the easiest so far in 2025. I'm encouraging listeners to actively seek out friends' birthdays so you don't have to rely on social media to know the date. Of course the next step is to acknowledge friends on their birthdays, again not only relying solely social media. 

The rest of the episode explores the emotional complexities surrounding birthdays, comparing how other friends' birthdays get celebrated, and why I believe in planning your own parties. 

While talking I realized we need a part two of this topic because I introduced many more questions than answers. I'd love to hear your thoughts and if celebrating friends' birthdays and your own brings up any feelings. I definitely shared some! Reach out any time at [email protected] or anonymously here. 

Find the past friendship challenges here. 

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.

 

THIS WEEK'S SPONSOR: Download Slowly to make a genuine friendship today. It’s free on the App Store and Google Play.
Download link: https://open.slowly.app/miXL/54lnblyi