The Connection Code with Rachel and Jeana

What turns “I attended an event” into “I found my people”?

This week, Rachel and Jeana welcome Kelsey Gilbert-Kreiling, founder of Week of the Website and co-founder of event-ticketing platform Eventually, for a conversation about gathering, belonging, and using technology to bring people closer.

From the first click to the welcome at the door, Kelsey shares why the little details shape how people feel—and what makes them want to come back. We talk about being the friend who reaches out first, staying connected when motherhood and entrepreneurship shrink your available time, and finding a community where you can be honest about the hard stuff. Plus, Kelsey shares how preparing for maternity leave changed her business and why her favorite advice is simple: “You can just do things.”

In our show-and-tell, Rachel shares reporting on people publicly putting out the call for friendship, and Jeana revisits her own 30 Days of Friends challenge.

A BIG thank-you to Eventually for sponsoring this season of The Connection Code! We’re so grateful to Kelsey and the Eventually team for helping us keep these conversations going—and for building tools that help people gather. Eventually brings event ticketing directly to your Squarespace website, with your branding and no per-ticket platform fees. Learn more at eventuallyticketing.com.

Media mentioned in the episode:

• Eventually — Kelsey’s event-ticketing platform.
• Week of the Website — Kelsey’s website agency.
• “How to Make a Friend: Tell the Whole World You’re Looking for One” — Rachel Wolfe’s Wall Street Journal article from Rachel’s show-and-tell.
• Invisible Things by Andy J. Pizza and Sophie Miller — the children’s book Kelsey brought home from Squarespace Circle Day.
• Bon Vivant Cakes workshops — the Chicago classes Kelsey highlights when discussing memorable experiences.
• EO Chicago Accelerator — the entrepreneur community Kelsey credits with helping her grow.
• Little Plains — the studio founded by Kelsey’s dream connection, Emmett Shine.

Remember when having a friend group felt effortless? There was always someone to grab dinner with, a group chat full of plans, and maybe even a standing softball game or BYOB night. So why does finding—and keeping—that kind of group feel so much harder as an adult?

In this episode of The Connection Code, Rachel and Jeana explore the magic and the messiness of friend groups: what brings people together, what pulls them apart, and what it takes to keep showing up for one another as life changes.

They talk about the challenges of distance, busy schedules and group chemistry; the role of the “social chair” who keeps everyone connected; and why shared activities can make friendship easier. Jeana also shares what it’s been like to build new connections after moving to Michigan, while Rachel reflects on the friend groups she’s loved—and the heartbreak of watching one fall apart.

Plus, they get into the ideal size for a gathering, the dynamics of couple friendships, and a conversation about money, friendship and whether two friends need to sit together on a flight.

Whether you’re missing an old group, hoping to find a new one, or wondering how to keep the people you love close, this episode is for you.

Media:

• What Is the Ideal Size of a Get-Together? — the evidence brief drawing on the Canadian Social Connection Survey.
• Expecting Together — the prenatal education and community program we share in show and tell.
• Eventually Ticketing — our season sponsor - use code CONNECT10
• The Instagram post where Adam Grant talks about friendship group size here

What’s the worst that could happen? For Rob Katz and Kevin Boehm, a four-hour conversation over coffee turned that question into the beginning of Boka Restaurant Group.

This week, Rachel and Jeana welcome restaurateur Rob Katz for his first podcast interview—and a candid, funny conversation about taking chances, building trust, and making people feel seen. From arriving in Chicago with $1,200 to discovering hospitality during an unexpected bartending shift, Rob shares how relationships shaped his path and why a lasting business partnership starts with complementary strengths.

We talk about why the customer isn’t always right, how Rob maintains close friendships without social media, and the unexpected joy of finding a new crew later in life. Plus: raising thoughtful, hardworking kids, asking questions even when you feel inexperienced, and a few memorable encounters with very famous restaurant guests.

Before the interview, Rachel and Jeana reflect on the risks that changed their own lives. Afterward, Jeana brings The Five Star Weekend to show-and-tell, sparking a conversation about girls’ trips, blending friend groups, and remembering who you’re there to support.

Media:

• Rob Katz’s official bio
• Boka Restaurant Group
• Gingie — the restaurant Rob specifically invites listeners to visit.

• The Five Star Weekend on Peacock
• The Five-Star Weekend by Elin Hilderbrand — the book behind the adaptation.

A diploma doesn’t come with instructions for making friends, navigating workplace expectations, or walking into a room full of strangers. So where do we learn those things?

This week, Rachel and Jeana welcome Heather Redisch, creator of Adulting 101 Masterclass, for a conversation about building confidence and connection through the everyday experiences that stretch us. Heather shares what she’s learning from coaching Gen Z, why managers should say the unwritten rules out loud, and how parents can help their kids build independence without smoothing away every challenge.

We talk about giving yourself time to settle into a new city or job, why one meaningful connection makes a networking event worthwhile, and how small, uncomfortable moments become opportunities to grow. Plus, Rachel and Jeana reflect on advice they’d give their younger selves—and share why ordinary errands are better with friends and putting our phones away can help us be more present.

Whether you’re starting your adult life, raising someone who is, or navigating a transition of your own, this episode is a reminder that you don’t have to have everything figured out to take the next step.

Media mentioned in this episode:

• Adulting 101 Masterclass
• Heather's Instagram: @adulting101_masterclass
• Heather's Adulting 101 Masterclass podcast
• the book Anxious Generation
• Priya Parker's new book, The Art of Fighting
• Everything is better together - The American Time Use Survey
• The University of Chicago's Train Study
• Read Phoebe Bridgers' phone-free event policy here

What’s the difference between collecting contacts and building real relationships?

Award-winning communications executive—and lifelong super-connector—Jon Harris joins us to share what more than three decades of bringing people together has taught him about curiosity, generosity and the relationships that remain long after jobs and titles change.

Jon opens up about the difficult childhood that shaped his commitment to helping others, why he believes the best networkers give without keeping score and what he has learned about asking for help during a professional transition of his own. He also introduces us to the Truffle Club, the trusted community of communications leaders he created during the pandemic, and reminds us why we should never let someone’s title stop us from saying hello.

Plus, Jeana and Rachel debate the increasingly popular wedding-day Irish goodbye and reflect on Dolly Parton’s legacy of generosity, joy and making the world a little brighter.

This episode is sponsored by Eventually. Visit eventuallyticketing.com/the-connection-code and use code CONNECT10 for 10% off your first year.

Media:

• Jon Harris: LinkedIn and Instagram @jonjayharris

• Dolly Parton’s Imagination Library: Learn about the book-gifting program
• Coyote vs. Acme: Official movie site and trailer
• Dare to Serve by Cheryl Bachelder here
• SocialWorks: Chance the Rapper’s Chicago nonprofit

What does it mean to love a place deeply and know when it’s time to leave?

New York Times bestselling author and Pulitzer Prize finalist Xochitl Gonzalez joins Jeana and Rachel for an expansive conversation about the places that make us, the people who remember our earlier selves, and the courage it takes to enter a new chapter.

Xochitl reflects on Brooklyn as both a hometown and a living archive. She also talks about writing Last Night in Brooklyn as one final love letter to the place that shaped her. She shares what decades-long friendships have taught her about grace, why closeness doesn’t always require constant contact, and how pre-digital friendship allowed people to become part of a community without feeling watched.

She also opens up about beginning her writing career in her 40s after years as a luxury wedding planner, the way class can narrow our sense of what’s possible, and why we should periodically reconsider our own “aperture of opportunity.” Plus, Xochitl talks manifestation, intergenerational mentorship, the connections she still hopes to make, and learning to trust that the road we started on isn’t necessarily the one we have to stay on.

Before the interview, Jeana and Rachel share moments when an improbable future felt inevitable. And in Show & Tell, they consider children’s autonomy online and whether we should ask permission before sharing photos of the people we love.

Media in this episode:

• Xochitl Gonzalez’s website
• Last Night in Brooklyn
• Olga Dies Dreaming
• Anita de Monte Laughs Last
• Need Blind: A Memoir of Class and Climbing in America
• Xochitl’s Substack
• Xochitl on Instagram

• Billy Joel: And So It Goes — the documentary that led Xochitl to a remarkable new connection.
• “Robby Hoffman Will Always Feel Poor, No Matter How Rich She Gets” — the New York Times interview Rachel references.

• Eventually Ticketing — use code CONNECT10 for 10% off the first year.

People-pleasing can look like kindness—but is it actually bringing us closer to one another?

In this episode, Rachel and Jeana examine how people-pleasing shows up at work, in friendships, in romantic relationships and even in hospitality. Inspired by Adam Grant’s writing on the subject, they explore the fear of disappointing others, why saying no can feel so loaded and how trying to earn someone’s approval can create an “authenticity gap” in the very relationships we’re hoping to strengthen.

They also discuss rejection as data, the difference between caring for someone and managing their feelings, and why clear communication may be one of the kindest relationship tools we have. Plus: a simple daily journaling practice, an invitation dilemma involving a Mother’s Day brunch and the question we can ask whenever we feel ourselves slipping into people-pleasing mode: Is this actually bringing me closer to this person—or am I simply trying to avoid discomfort?

Media mentioned in this episode:

• “The Truth About People Pleasing” by Adam Grant — the newsletter that inspired the conversation and includes the Kristen Bell example.
• "I Got Rejected 101 Times” by Emily Winter — the essay Jeana references about intentionally becoming more comfortable with rejection.
• “I Got Uninvited From Mother’s Day Brunch Because I’m Not a Mom” from Kramer & Jess — the call-in segment discussed during Show & Tell.
• Eventually — listeners can use code CONNECT10 for 10% off their first year.

• The Likability Trap by Alicia Menendez
• Suzy Welch’s Becoming You

What if the goal of a disagreement wasn’t to win, but to make the next conversation possible?

Rachel and Jeana talk with Harvard professor Julia Minson, author of How to Disagree Better, about what happens when we assume we already understand the other person. Julia shares a late-night disagreement with her daughter that went sideways, why curiosity needs to be spoken aloud, and a simple “curiosity sandwich” for expressing your view while staying open to someone else’s.

They also explore why personal stories can build trust where facts alone may fall short, and how asking a follow-up question shows someone you’re listening. Whether the disagreement is with a child, a friend, or a colleague, this episode offers ways to stay connected through it.

This season of The Connection Code is sponsored by Eventually. Visit ⁠eventuallyticketing.com/the-connection-code⁠ and use code CONNECT10 for 10% off your first year.

Other content to dig into:

• Read Julia's book ⁠How to Disagree Better⁠
• Dig into Julia's ⁠workshops and research⁠.
• ⁠The CBS News story about the four-year-old who brought his neighborhood together⁠—Rachel’s show-and-tell.

What happens when kids put down their phones and have the freedom to simply be kids?

Rachel and Jeana sit down with Tommy Hoffman, executive director of Herzl Camp, to explore why summer camp remains one of the rare places where young people can practice the art of conversation, navigate conflict, develop independence, and form meaningful friendships through repeated, real-life experiences.

Tommy shares how returning to camp after a 30-year career helped him find his “A+” calling—and what he has learned from watching hundreds of campers grow, connect, try new things, and become more confident in who they are. Together, they discuss camp as a sanctuary for childhood, the difference between witnessing connection through a screen and experiencing it for yourself, and the lessons adults can borrow from camp to build richer relationships of their own.

Plus, Rachel and Jeana tackle one of the least glamorous—but most important—parts of adult friendship: Who is responsible for making the plans? They talk about the invisible labor of being the group planner, rotating responsibility, creating standing dates, and why we could all use more low-pressure “barefoot plans.”

Media within:

• Herzl Camp
• The Anxious Generation by Jonathan Haidt
• Eventually Ticketing — with code CONNECT10 for 10% off the first year
• Cut article about the AI-driven summer camp here
• This Closure Instagram video discussing the weight of being the friend who makes plans!

We’re back for Season 3—and after 50 episodes of talking about friendship, connection and the relationships that make life better, we’ve learned a few things.

In this season opener, Rachel and Jeana look back at the conversations from Season 2 that have stayed with them, changed their behavior and even sparked new friendships in real life. They talk about why friendship can feel harder in adulthood, the invisible work of being the person who always makes the plans, the vulnerability of feeling left out, and why chemistry alone isn’t enough to turn someone into a close friend.

They revisit lessons from guests including Danielle Bayard Jackson on why friendship requires effort, Leslie John on the power—and limits—of vulnerability, Sara Haines on curiosity as a tool for connection, Laura Sanchez Greenberg on building a personal board of directors, Suzy Welch on the freedom to disagree, and more.

Plus: the unexpected connections that continued after the microphones turned off, why adults might secretly be craving friendship camp, the beautiful story of Japan’s “wind phone,” and one very small-world dinner party moment that proves you really never know where a cold email might lead.

Season 3 is here. Let’s get connected.

In this episode:

• Why friendship doesn’t have to feel effortless to be meaningful
• The emotional sting of a friendship misunderstanding
• What 50 episodes have taught us about vulnerability and curiosity
• Why adults need more unstructured time together
• How to stop defaulting to “What do you do?”
• The Season 2 conversations Rachel and Jeana are still thinking about
• What happens when podcast connections become real-life friendships
• The case for friendship camp

Mentioned in this episode: Danielle Bayard Jackson, Leslie John, Sara Haines, Laura Sanchez Greenberg, Suzy Welch, Morgan Radford, Dr. Carly Thompson, Shabnam Mogharabi, Lilliana Vazquez, Lily Engelbret and Sarah Spain.

This episode is sponsored by Eventually, event ticketing and registration that lives directly on your website without per-ticket fees. Visit eventuallyticketing.com/theconnectioncode and use code CONNECT10 for 10% off your first year.