SFTR: Dinner With a Stranger
In the current chapter of my life—basically quitting The Comfort Zone on every front—I’ve needed people and connection more than ever.
“We’re home! Come play pickleball with us!”
You might guess this message came from a longtime friend excited to catch up with me during a quick stay in Utah. But nope. It came from a friend I made February 2023 in Athens, Greece. She’s stayed in touch with me, I’ve stayed in touch with her; that’s how this whole friendship thing goes.
We may seem like an unlikely pair of friends, with seemingly the only thing in common being our religion (we met at church in Greece). Wynette and her husband are retired, their children are all grown, and they’ve lived for decades in a small farming town.
But she feels like a kindred friend, for the following reasons:
She has a mutual interest in being friends and staying in touch. She had, or made, room in the inn—so to speak—for friendship.
She’s funny. I’ll do almost anything for and with a funny person. She’s also kind and blunt and uniquely herself and loads of other good things.
We met on an adventure. She and her husband were volunteering with our church to help nonprofits and NGOs provide relief to those who most need it. And I was in my Mid-life Gap Year of exploration.
We’re in a lonely time, y’all. If you’re reading this post, it’s probably because you too have interest in more connection and more friends. COVID and social media and changing relationships have done a real number on all of us, and the downside of working your job or business from home is—shocker—fewer people in your daily life.
In the current chapter of my life—basically quitting The Comfort Zone on every front—I’ve needed people and connection more than ever.
Maybe you’ve got time with people on screens, but you crave more real life friends and connections. In the current chapter of my life—basically quitting The Comfort Zone on every front—I’ve definitely needed people and connection more than ever. And I’ve found so many lovely people who are wanting the same.



I’ve basically been reading people for friendship potential for the past 18 months, and here’s one recent story of how it’s gone for me:
A story:
Before wrapping up my three-day tour of America’s Historic Triangle to head inland, I took myself out for a nice seafood dinner at Bennett’s. There was live music on the patio and one seat left at the outdoor bar. I noticed my neighboring fellow solo traveler had a book, and when I came back from the bathroom, I struck up conversation with something clever like, “I see you have a book.”
Just kidding, it was more like, “I promise I won’t talk at you all night, but it’s so nice to see someone else with a book. I brought one, too.” And then we gabbed like old friends for the next hour and a half about books and everything else. Had Isabelle returned to her book or acted disinterested, I would happily have gotten lost in my book. Tales of the Alhambra, if you care to know. Side note: I didn’t know until last year that the Alhambra is a real place—one of the neatest I’ve now visited (see below).
But she—a recent college graduate exactly half my age—was happy to chat, and so we did. It’s amazing how easily some of these conversations can flow and the things people will share:
She was introduced to a website in middle school that shows job expectancy, and by studying this website she decided in high school to pursue environmental science over something specific to sustainability. Who is thinking like this in middle school? Pretty sure Middle School Emily was mostly thinking about whether she had the right Jansport backpack and when the next math class Pickle Barrel sandwich party would be.
Isabelle was on her first solo road trip and her version of this included tent camping on dispersed land, AKA a prime location for a Dateline story. Her second night, not another camper was within screaming distance. She couldn’t even see her hand in front of her face, and regretted her choice of reading material—something like vampire camping horror. Who even knew that was a genre?!
She intentionally uses a flip phone. Mind blown. While doing a once-in-a-lifetime internship in the Amazon Basin last December, she frequently and unconsciously found herself scrolling on Instagram. She was super not okay with her level of smartphone addiction, so when she came home she ditched it for a flip phone.
We also talked about family, how her boyfriend is the only person around whom she immediately felt free to be herself (“he was the first person I didn’t feel like I had to wear a mask around”), about the volunteering she sought out during high school, about some of my travels, and about taking risks while still staying safe.
I don’t know if Isabelle and I will ever connect again, but I left her with my email and phone number, just in case she needed something with her broken-down truck situation, and because it felt like the right thing to do. We’re here to help each other out, right? Like our friend Ralph Waldo Emerson says:
The purpose of life is not to be happy. It is to be useful, to be honorable, to be compassionate, to have it make some difference that you have lived and lived well.
Jury’s out on whether I’m living well, but maybe it made some difference to my fellow traveler to know that, if she needed a friend, she had one in me. All I know is that our dinner friendship made my Williamsburg experience richer, and natural friendships like this wherever they happen make my life better.
I recognize that my experience as a still-solo woman may not match up with your life situation. You might always find yourself surrounded by your spouse or significant other or kids or friends. And even if you like them, you might still want or need more friends. This is the case for at least three of my readers (two of whom are married, one of whom has kids) who have shared with me recently that they wish they had more friends to do things with.
I also recognize that making friends while traveling is different than making friends in your town or city. Everyone can be in busy or comfortable mode and it can be easy to get in the same yourself.
But for those in the market for more connection and friendship, here are a few approaches that have helped me in situations near and far; perhaps they’ll jog some new ideas or motivation for you:
Be open. There’s an openness, a vulnerability, about travelers that serves us well in our ordinary lives.
Go new places or do things where you’re out of your comfort zone, and don’t be shy about vocalizing that it’s out of your comfort zone. Leading with something like, “I’m new here, mind showing me the ropes?” has never failed me for making a new friend while doing something uncomfortable.
Take time to be friendly even in quick exchanges. I have an aunt who always says, “Hey, how are ya?” to every one she sees including the person washing hands next to her in a bathroom. It’s worth the effort to acknowledge the people in your space.
Suggest plans or swapping contact information with those you like talking with. It can feel vulnerable to express your interest in continuing the conversation or doing something together. But worst case, they’ll say, “Naw thanks,” be flattered, and you’ll get over feeling awkward after an hour. Best case, you might have found the friend you’ll be calling in five months with exciting social invitations like, “Hey, I’m running to Target. Wanna come?”
What’s your current friendship life like? Do you have all the friends you need? I doubt it, and that’s not because I doubt you in the slightest. We all need meaningful friendships and mutually-boosting friendships that meet us in our current stage of life. Even influencers like Mel Robbins, with gobs of money and families and lots of social connections, still need and want more everyday friends. If you ever want to coordinate a trip to Vermont to try and make friends with Mel, just let me know. In lieu of that, though, what are you going to do wherever you are to cultivate more friends?
We all need meaningful friendships and mutually-boosting friendships that meet us in our current stage of life.
As for me, I’ll be joining a local pickleball association, get involved with my church, look for volunteer opportunities, and keep talking to strangers. And writing for my fellow dreamer friends—you may not know, but I do very much consider you my friends.
Three questions I’d honestly love to hear your answers to:
How satisfied are you with current friendship situations?
What type of friend would you most like right now?
How would someone’s life be better for having you in it as a friend?
P.S. If you liked this post, please consider sharing it with someone who’s added friendship to your life, or send them a text letting them know their friendship has made a difference. Who doesn’t want to know that they’ve had an impact? That’s right, no one.