“My sister and your sister are friends, so we’re going to be friends, too.”
I was nine years old, and just like that, we were.
Nearly 44 years later, I’m writing this from 35,000 feet, en route to a five-day retreat in Hawaii where I’ll know exactly one person. And I’m nervous.
Making friends was remarkably uncomplicated back then. Or at least that’s how I recall it.
My first friend became my best friend for more than four decades. It wasn’t a friendship that developed over time. It arrived with a declaration.
I showed up wearing the same plaid jumper and polyester oxford shirt as every other girl in fourth grade. There was certainly no competition for whose first-day-of-school outfit was the most poppin’. We were all losing in that category.
(If I weren’t 5,000 miles from home, I’d share photographic evidence. Honestly, it’s rather tragic. I’ll reserve that for another article.)
Maybe it was that sameness that erased my new-kid-on-the-block jitters. With all the confidence of a polyester-clad rockstar, I approached the one girl I knew of and declared our friendship.
No awkward introductions, sheepish small talk, or wondering whether she liked me.
I sometimes wonder what happened to that fearless little girl. Because the thought of walking into a room full of strangers still makes me nervous.
Apparently, making friends was easier when I was nine.
So on this flight, I’m writing down what I know about getting through a room full of strangers, along with the five commitments I’m making to put it to work.
When Did Being Social Become So Complicated?
While I grew up in a big city (I’ll give Minneapolis those props), I lived in a relatively small world.
I entered Breck School and graduated with fewer than 100 students, the majority of whom I met during my elementary school days.
My college roommate was the very same girl I’d declared my friendship intentions to in fourth grade.
During our freshman year, the two of us watched a blond-haired guy drive past our dorm window in his green Mustang convertible. That 1992 version of Bo Duke (yes, I grew up a Dukes of Hazzard fan) became my college sweetheart, first husband, and the father of my daughter.
After college, we moved to his hometown, where I built friendships through the community and relationships he already had.
Looking back, I realize that I rarely had to start completely from scratch. There always seemed to be an entry door already open for me that made those first introductions easy.
As I sit on this plane to Hawaii, surrounded by couples traveling together, I’m realizing how much I’ve relied on having someone beside me. Even during the years I was widowed after losing George, my daughter and dear friends were always by my side. Now that I’m remarried, Dave is my person.
I’ve lived a lifetime in companionship. What a blessing.
I’ve always had a wingman.
And today, I don’t.
I’d Rather Speak to 2,000 People Than Mingle With 100
I know how absurd that sounds. But it’s true. And I know I’m not the only one out there who loathes small talk.
I would much rather stand behind a podium and speak to an audience than circulate through a cocktail party full of strangers.
I’ve taught rooms full of students and spoken into microphones in front of enormous audiences without an ounce of perspiration.
But the moment I walk into a room of people holding cocktails, making polite conversation, and exchanging niceties about careers, sports, and the stock market, I’m instantly crawling out of my skin.
I’d rather be anywhere else.
I fucking hate small talk.
There. I said it. Consider that my 52-year-old declaration.
My husband, on the other hand, could small-talk his way through the grocery store.
He can strike up a conversation with absolutely anyone. The person standing next to him in the produce aisle. The cashier. The guy bagging the groceries. Anyone wearing Notre Dame swag.
Talk about built-in best friends. That’s a community that instantly becomes your ride or die upon receipt of a diploma. Their icebreaker looks something like, “What hall did you live in?”
When I hear that question, I know I’m in for a 20-minute diatribe about everything Irish and the inevitable exchange of vCards.
Meanwhile, I’m standing beside him, practically tugging at his arm like a five-year-old asking, “Can we go home now?”
Don’t get me wrong. I love this about him. And it’s not that I dislike people. Quite the opposite.
I love meaningful conversations. I’m endlessly curious about people and what makes them tick. Perhaps it’s the curious (and inherently impatient) part of me that can’t stand small talk. I’d rather get straight to the meat.
Just yesterday, I met the hairdresser in the chair next to me. Within minutes, we’d diagnosed the source of his nervous system overload and were rethinking his entire business model.
Clearly, being a conversationalist isn’t the issue. It’s the obligatory social gymnastics and the feeling that I need to perform in certain settings that send my nervous system spiraling.
I just can’t with the cringey cocktail party questions. You know the ones. What do you do? Do you have kids? Any exciting travel plans?
Sometimes I wish we could skip the pleasantries and get straight to the interesting stuff, like nervous system regulation.
Mine and yours.
Why Am I So Awkward?
When asked, I’m never quite sure how to answer whether I’m an introvert or an extrovert. I’m not going to Google the answer, but I suspect I could fairly be diagnosed as both. A mutt of sorts, and I kind of love that for me.
There’s no doubt that I can be outgoing, animated, and comfortable commanding a room where I feel welcome and wanted. I happen to make a great board member for this reason. Combined with my quizzical nature, I’m the first to ask a question and lead a discussion.
But I also love my solitude.
Given the choice between an evening of superficial conversation and a quiet night at home, home wins all day long and not because I need a reboot. It’s avoidance.
For years, I chalked up my discomfort in certain social situations to being an introvert. But the more I think about it, I don’t think that’s it at all.
When I walk into a room full of strangers, I become this awkward version of myself. One who looks nothing like the woman sitting at the boardroom table.
It’s as if I arrive with a spotlight turned directly on me. I realize that sounds completely narcissistic, but that’s not what I mean.
I’m the one holding the light, examining myself under the 10x magnifying mirror.
The internal dialogue is exhausting. It revolves around my concern for looking good and those familiar limiting beliefs: I don’t belong. I’m not good enough.
Instead of being the deeply curious extrovert, I become the self-conscious introvert who wants nothing more than to be home in her pajamas.
Getting Out of My Own Way
Here’s the frustrating part. I know better.
I’ve spent years teaching yoga. I owned a studio. I’ve led trainings and attended even more. I’ve studied human behavior and learned how our thoughts influence the way we experience the world. I’ve even spent considerable time working to recognize and dismantle the limiting beliefs I’ve carried around for decades.
And trust me, I’ve come a long way. Thank God!
Yet somehow, put a cocktail in my hand and surround me with strangers, and all that wisdom seems to disappear.
Self-awareness doesn’t automatically translate into changed behavior. That, too, requires work, which I’ll be committed to for a lifetime. After all, aren’t we all a mountain with no top?
I can’t decline every invitation for the sake of avoidance. I need to confront this fear. And while I’m busy rewiring the neural pathways responsible for some of the patterns that hold me back, I realize there’s another way to approach the cocktail party conundrum. One that doesn’t require years of perfecting therapeutic models.
What if this becomes less about me and more about the people around me? What if I turn the spotlight?
When I think about the people I truly enjoy spending time with, they’re the ones who make me feel comfortable being myself, not some performative version of me.
They ask thoughtful questions and remember little pieces of me from a previous conversation. They listen, and I mean truly listen, not the distracted kind or the kind where someone is simply waiting for their turn to respond. They make me forget I was ever uncomfortable in the first place.
I’ve met plenty of people at cocktail parties who are the loudest in the room, can deliver an incredible joke, and impersonate someone in a way that’s worthy of an Academy Award. But the people I remember most aren’t necessarily the ones who entertained me. They’re the ones who made me feel seen and heard.
Isn’t that a basic human need?
Perhaps I’ve been so busy worrying about how I’m coming across that I’ve forgotten something rather obvious.
The conversation doesn’t need to be about me. What a relief to take myself out of the spotlight.
The Art of Getting Beyond Small Talk
I have a friend who’s particularly good at this. I should have taken a few cues from her playbook years ago.
She’s masterful at redirecting conversations. Most people love to talk about themselves, and she has a brilliant way of answering a question with another question.
If someone approaches her at a cocktail party and asks, “Hey, how have you been?” her response might sound something like this:
“I’ve been great, but those earrings are stunning! There has to be a story behind where you found them.”
Just like that, she’s moved beyond the obligatory pleasantries and given the other person something interesting to talk about.
Having a handful of these redirects or questions in your back pocket is a great way to move toward more meaningful conversations.
Rather than asking someone about their kids, ask, “What have your kids gotten you interested in lately?”
Instead of asking about an upcoming vacation, ask what experience they wish they could have all over again.
And if you find yourself in the career corner, ask how they unwind from work. What’s their idea of a perfect weekend?
These questions are open-ended and allow the conversation to evolve. They invite us to listen, learn, lean in, and ask more.
They move us beyond the surface and make room for connection.
When All Else Fails
This is going to take practice. You’re going to have to sit through those initial moments of discomfort, and not every conversation is going to be a win.
When you feel things spiraling and your awkward self making an appearance, try this.
Stop talking.
Seriously. Let there be silence.
I worked with a woman years ago who was masterful at holding space without saying a word. I was fresh out of college and new to the professional world. I’d never experienced anything quite like it.
Her silence made me so deeply uncomfortable that I’d start spewing words. Word vomiting, oversharing, and I mean way oversharing.
I’d leave her office thinking, OMG, I can’t believe I just shared that!
Rather than becoming that version of me, walking away ruminating over everything you wish you hadn’t said, trust yourself enough to allow for a little silence.
Give it a beat. Chances are, the other person will be perfectly happy to take over the mic.
The other important thing to remember is that not every conversation is going to be a success story where you part as new best friends. That’s not the point.
Some interactions will feel effortless, while others will be as painful as a visit to the dentist without Novocaine.
There will be inevitable pauses, and you might say something you later look back on and think, WTF just came out of my mouth?
Give yourself grace. Invite in both humility and humor. Learning to laugh at yourself can help defuse the rising discomfort and make it possible not only to survive the moment but perhaps even enjoy it.
The older I get, the more I realize that I don’t need everyone to like me, and I don’t need every acquaintance to become a close friend.
Some connections are simply meant to be enjoyed for the time and place in which they occur.
Putting My Own Advice to the Test
The timing of this article feels particularly appropriate. ’Tis the season for holiday parties, when there’s no shortage of opportunities to practice and ultimately flex this new pattern of social ease.
Wouldn’t it be nice to walk into the next party without a hint of social anxiety? Rather than racing to the cocktail bar for a round of liquid courage, imagine entering with grace and ease, confidently and casually saying hello to people along the way.
What if that first sip feels like sheer enjoyment and festive cheer rather than a shot of raw ginger gulped down to ward off the evil social anxiety spirits?
I’m kicking this into high gear myself. As luck would have it, I’m about to have the perfect opportunity to test my own advice.
Which brings me back to this flight and the five-day founder’s retreat waiting for me in Hawaii.
This was a completely last-minute trip. I was invited by a friend who is among the event hosts, which means I’ll know exactly one person when I arrive. And he’ll be busy hosting rather than holding my sweaty palm.
Unfortunately, my husband is off meeting new friends of his own this week, which, of course, gives him zero anxiety.
I even attempted to coerce him into changing his plans to join me.
Having him by my side would be the equivalent of having that door held ajar again. And he knows that about me.
Instead, he gave me a resounding amount of encouragement, left me a couple of love notes to that effect, and hopped on his own plane headed elsewhere.
This particular retreat brings together an impressive group of founders and entrepreneurs for several days of conversation, connection, and experiences. I’m genuinely excited to be there.
And my socially awkward self still wants to retreat to the safety of my hotel room.
A spa day, bathrobe, and room service? Yes, please.
There is something deeply ironic about the fact that my friend, the host, just sent me a text that reads, “Can’t wait to introduce you to so many amazing humans.”
Meanwhile, I’m sitting here writing about how to become more comfortable in social situations, en route to a beautiful Hawaiian island where my nervous system could very well go into a tailspin.
One would think that by now I would have overcome this dreaded feeling, but at nearly 53, it still rears its ugly head.
So what does my nervousness look like?
Overpreparing, of course.
I’ve reviewed the agenda. More than once. I’ve completely overpacked because I feel the need to be prepared for anything and everything.
Of course, I got my nails done. To be fair, I would be doing that anyway.
I recognize that my concern with looking good is completely present. It has less to do with vanity and everything to do with imposter syndrome and wanting to show up as part of the group rather than feeling less than everyone else.
I know. I know. There’s still so much to unwind in this old soul of mine. I’m just being real.
Ultimately, I have to remind myself of the very thing my husband keeps telling me, and something I know to be true.
I was invited. Nobody is expecting me to prove that I belong there.
Now I just need to get out of my own damn way.
My Five-Day Experiment in Social Ease
I’ve decided to give myself five commitments for my five days in Hawaii.
I can write about social ease all day long, but at some point, I actually have to practice it.
So here goes.
1. Choose Participation Over Isolation
There is no one who loves to live in a bathrobe more than me. I’ll save that for another trip (more to come on that).
Rather than hide out in the extraordinary suite that awaits me, I’m going to double down on the activities outside the scheduled programming.
There’s 7 AM yoga, morning meditation, and group reflection walks through the tropical landscape surrounding the resort. Yes, of course, these all sound amazing.
Another version of myself (the one I left behind in Florida) would choose to head to the gym and then retreat to my room to sip my morning matcha from the quiet balcony.
While there’s nothing inherently wrong with those choices, this week I’m deliberately choosing the group experience.
I’m not traveling all the way to Hawaii to hide in my room.
2. Sit Somewhere New
This sounds so silly. Yet I know myself well enough to recognize that I adopt a habit when I enter an unfamiliar social environment.
When I find the one or two people I connect with, I tend to gravitate toward them at every event, making them my own comfort zone.
Before I know it, I’ve spent the entire experience with the same people. Does anyone else relate to this?
This week, I’m changing that. I’m committing to sitting with someone new at every meal.
Honestly, even writing this, I feel like I’m imparting wisdom to an elementary school child.
If I’m truly going to stretch outside my comfort zone, I need to give myself the opportunity to meet people I might otherwise never get to know. Landing in the default seat won’t allow for that.
And as I was gently reminded in that text, amazing people await my days ahead.
3. Raise My Hand
This one might be more uncomfortable than the others.
The retreat includes some dynamic conversations and breakout sessions with people whose experiences and accomplishments I genuinely admire. Yes, of course, I did a LinkedIn deep dive when the list of attendees arrived over the weekend.
While I could just sit back and listen without necessarily looking like a wallflower, I’m committing to contributing to the conversation.
Why not? What if my question sparks a discussion or gets someone else thinking about something they hadn’t considered?
4. Know Who I Am Without Rehearsing Who I Need to Be
I’ve been spending considerable time lately thinking about how I want to be known. I even wrote a whole article on it.
These next few days present an opportunity to put some of that clarity into practice by articulating who I am and what I’m up to without stumbling through an awkward explanation or launching into a rehearsed elevator pitch.
I have a tendency to start editing myself depending on who’s asking the questions. My intellectual self starts considering the audience. How much do I want to share? What’s relevant? And a whole host of other questions.
Before I know it, I’m so busy deciding which version of myself to introduce that I’ve made a simple question unnecessarily complicated. And then I end up sounding completely inarticulate.
I want to be comfortable enough with myself to share freely without editing my life.
5. Do One Thing Every Day That Scares Me
This is my favorite commitment. It’s one that recently landed me at a weeklong program that was by far the most impactful thing I’ve done for myself. Needless to say, I’m leaning into it again in Hawaii.
Every day, I’m going to say yes to something I might ordinarily avoid. I have no idea what that will look like, but when I hear that voice in my head or feel the constriction in my throat or tightness in my chest, that’s usually a good starting point to explore.
It might look like an excursion I wouldn’t normally choose or initiating a conversation with someone who, from a distance, intimidates me a little. Maybe it’s getting onto the dance floor instead of standing on the sidelines watching everyone else have fun.
I’ve written before about my desire to reclaim a more playful side of myself. Here’s my opportunity, and I’m going to embrace it one uncomfortable yes at a time.
A Little of That Nine-Year-Old Confidence
As I sit here thinking about what awaits me in Hawaii, I can’t help but think about that nine-year-old girl in Minneapolis who had absolutely no problem walking up to another little girl and declaring they were going to be friends.
She had confidence. She had sass.
I’m not entirely sure where it came from or where it went. Somewhere along the way, that confidence gave way to concern about what other people thought of me.
I’m certainly not going to start walking up to strangers and declaring we’re going to be friends. But I wouldn’t mind borrowing a little of that nine-year-old’s confidence. And maybe even a little of her sass.
So here I go.
I’ve got five days to put my own advice to work. I suspect there will be some uncomfortable moments, a few conversations I wish I’d handled differently, and hopefully plenty of laughter along the way.
I’ll report back.
Always EDITing,
Leslie
As always, please drop a comment. If you have a go-to cocktail party question or one that helps move a conversation beyond small talk, please share it. You might just help another reader navigate the cocktail party season ahead.
P.S. If my virtual assistant gets her wish, perhaps there will finally be a reel to prove I was there. My daughter did just teach me what B-roll is, after all.
ABOUT ME
I am still working on the perfect bio.
I am a writer. Former yoga studio owner and marathon runner. That seems like an oxymoron, I know. My body thinks so, too.
I am also a bunch of other formers that look better on a LinkedIn page than on Substack.
I lost my husband nearly four years ago. It changed my perspective on everything and handed me a new life I never asked for but had to build.
I am constantly exploring discernment, what we value, and the choices that shape our lives.
My articles are weekly. No two are ever alike.
I am grateful you’re here, helping shape a community that has given me purpose and passion in the most unexpected and beautiful way.
What an inspiring article! I am more like your husband (🤣) but in my line or work I mainly meet people who feel isolated and disconnected, and social anxiety seems to be a constant there. I suggest most of what written here (behavioural activation here we go), especially the spotlight trick. Also, I have not seen it here but maybe you do this: I suggest meeting people through activities rather than parties/pubs etc. That is because if theres a shared activity, like say gardening, the spotlight is automatically on the activity and small talk is replaced by talking about the activity and why we chose to do it - this always works wonders :)