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Wednesday, 24 June 2026
The Friendship Case for Getting Out of Your Routine
Why travel, strangers, and small social risks are good for connection
Last May during the 2025 Dear Nina Friendship Challenge, I urged readers and listeners to change the venue in a friendship. For example, if you and a friend always walk, try cooking a meal together or going out to eat. If there’s a friend you only text, try picking up the phone. (I was less literal about “venue” in several examples.)
The idea was to shake things up and hopefully bring forth new conversations and new ways to connect. In other words, to deepen the connection, we sometimes need to get out of our routines.
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A different setting gives people new stories, new memories, and a break from the same old scripts. Funny enough, the last two episodes on Dear Nina: Conversations About Friendship seem completely unrelated to each other, but they get at the same core concept I was urging last May with “changing the venue.”
In episode #199 with my fabulous assistant producer, Rebekah Jacobs, we discussed taking trips with friends. We were not just talking about group trips. Even one-on-one trips are a special and memorable experience.
I admitted on that episode that I don’t travel with friends as much as I could (and should!). Rebekah is the traveling-with-friends pro. And she had so many practical tips for making it work. By the end I was convinced I need to make this a bigger part of my life now that I’m turning 50 at the end of this year. I wish I had not waited so long! (It’s not that I never travel with friends, but I don’t do it often at all.)
Rebekah and I don’t live in the same state, but she came in town for a mutual friend’s event so we got to take a silly photo together. She will be back in Minneapolis in July for Dear Nina Live! :)
I came into this conversation a little wary. Do I really want to talk to more strangers? On airplanes? At Trader Joe’s? (I complained about both in the episode.) But Gillian’s research—and her very practical way of talking about it—made a strong case for why these small, low-stakes interactions matter.
Every friend was once a stranger. Not every stranger is meant to become a friend, of course. That’s not the point. The point is that talking to people we don’t know gives us practice with the exact skills friendship requires: handling uncertainty, risking rejection, asking better questions, listening, and staying open to other people. It also just makes the world a kinder place!
Gillian and I also spoke about the “liking gap,” which is the encouraging finding that people usually like us more than we think they do. In other words, the awkwardness we feel after a conversation is often happening more in our heads than in reality. And these little social risks help us in all parts of our lives because taking them builds confidence.
Traveling with friends is a bigger social risk than talking to strangers since it involves money, logistics, being together for longer, inviting, organizing, and possibly being rejected by a person who matters to you more than a stranger does. Talking to strangers is a tiny social risk. But both ask us to set aside our usual way of moving through the world and change how we relate to our friends, to strangers, and to the people somewhere in between.
That’s the friendship case for getting out of your routine. Sometimes connection deepens not because we try harder in the exact same ways, but because we’re willing to change the setting, take the small risk, and stay open to what happens next.
My friend and the author of the book Modern Friendship(which I recommend constantly), Anna Goldfarb, just wrote a piece on Substack I appreciated so much called, “Rotten Devotion: The Friendship Dynamic Nobody Has Named” (The relationship dynamic where you are loved, supported, and expected to stay small.)
Live event this summer! July 29th. Tickets are on sale here.
Books, Shows, Finds, and Recipes
LISTENING: Still loving the new David Sedaris collection. I’m only allowing myself a little bit at a time, which is why this has been on my listening list for three weeks. I mix in a bunch of podcasts and even some music in the meantime.
READING: I’m almost done with Into the Blue by Emma Brodie. I’ve seen mixed reviews but I really like it. It reminds me of Gabrielle Zevin’s Tomorrow and Tomorrow and Tomorrow, which is one of my favorites. See my updated 2026 list for all the books so far this year.
TV: I just started the Netflix movie, Voicemails for Isabelle. SO good so far.
RECIPE: My 19-year-old daughter is home for the summer and cooking nonstop. I might be retired for the summer! She’s made several salads from Life-Changing Salads by Danielle Brown, which I’ve loved.
SHOPPING: It’s time to replace some of our water bottles. Everyone seems to be fighting over the few Owala ones we have so I’m getting rid of some very old random ones in the cabinet and getting a few more on sale at Target. (certain colors seem to be on sale)
Two Anonymous Letters You Might Have Missed (June is coming soon!)
Let’s connect outside of this newsletter: You can find me most often in the Facebook group, Dear Nina: The Group. All the social media links are below. I know I need to get rid of some them! Instagram | TikTok | YouTube | LinkedIn | My Website
The anonymous letters (and my answers!) come from the rawest places of friendship uncertainty. They deserve the most sensitive readers who are not going to roll their eyes, leave troll-ish comments, or make the letter-writer feel foolish for asking. If you’re willing to upgrade to this part of the newsletter, I know you’re there with the best intentions to be part of a community that’s not afraid to ask the tough questions and who will read the answers with an open heart. If that’s you, I’d love to see on the other side. :)
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