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Hi {{first_name|there}}, it’s Thomas.
Several years ago, as we re-emerged from our COVID isolation, I noticed something curious while attending those first few conferences and other meetup events I started to attend.
People would gather in quiet, distributed clusters around the room, drinks in hand, all seemingly waiting for someone else to make the first move. You could almost see the internal dialogue playing out behind their eyes: I'd love to meet someone new... but I don't want to interrupt. They probably already know each other. I'll just wait.
Of course, everyone else in the room was having the same conversation with themselves.
This is one of the great paradoxes of adult friendship. Most people want to expand their social circle, but very few are willing to endure the five seconds of discomfort required to begin.
The irony is that building social wealth doesn't start with making a new best friend. It starts much earlier, with something far simpler: turning a stranger into an acquaintance.
Every acquaintance you make becomes another weak tie in your network. We know from Mark Granovetter’s work that weak ties are among our greatest sources of new ideas, career opportunities, introductions, and perspectives because they move in different circles than we do. The larger and more diverse your portfolio of acquaintances becomes, the richer your social wealth grows.
The good news is that becoming someone who starts conversations isn't a personality trait.
It's a skill.
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Your Job Isn't to Make Friends
One reason people hesitate to approach strangers is that they place far too much pressure on the outcome of that singular interaction.
They assume every conversation has to become a friendship, but it doesn't.
Think about your social wealth as an investment portfolio. Some people become close friends. Others remain trusted colleagues. Many simply become acquaintances you enjoy seeing from time to time. Every one of those relationships has value because every person occupies a different place within the broader network of your life.
Your only job is to open the door to someone new.
Whether that someone eventually becomes a friend is something time will reveal, but first you have to get the conversation going.
Start With What You See
The easiest conversations begin with something that's already happening.
Social psychologists have found that shared attention creates an immediate sense of connection because both people are mentally focused on the same thing. That makes observational questions feel natural rather than intrusive.
"You look really focused. What are you working on?"
"Those look like fast running shoes. Do you run?"
"I couldn't help noticing your notebook. Is that for work or a hobby?"
The observation demonstrates that you're paying attention. The question invites the other person to tell a story.
People generally enjoy talking about subjects they know well, and no one knows their own life better than they do.
Invite Someone to Be the Expert
Another surprisingly effective conversation starter is asking for advice.
Human beings enjoy feeling useful. Psychologists sometimes refer to this as the "Ben Franklin Effect." Interestingly, people often become warmer toward those they've helped because our brains naturally assume we help people we like.
The advice doesn't have to be life-changing.
"I'm looking for a professional opinion. You seem like you know this world. What's your take?"
"I've been thinking about trying that restaurant. Have you been?"
"You seem to know a lot about cameras. If you were starting today, what would you buy?"
Advice transforms a conversation into collaboration. Rather than trying to impress someone, you're inviting them to contribute. That's a much easier place for connection to begin.
Follow Up on the Story
Almost everyone carries conversation starters without realizing it.
It could be a distinctive watch. A university sweatshirt. Hiking boots. A tote bag from another country. A lapel pin. An unusual notebook.
Instead of simply complimenting the object itself, become curious about the story behind it.
"That's a beautiful watch. What's the story behind it?"
"I've never seen that logo before. Where's it from?"
"You've clearly gotten some miles out of those hiking boots. What's your favorite trail?"
Stories are where relationships begin. Objects are simply the invitation.
When you ask about the story instead of the thing, you're signaling genuine curiosity about the person rather than making idle small talk.
Bonus points to you if you’re wearing/carrying your own distinctive conversation starter.
Sometimes "Hello" Is Enough
Of all the conversation starters, the simplest seems to also be the one we resist the most: just say, “hello.”
No clever observation. No perfectly crafted question. No rehearsed introduction.
Just enough courage to acknowledge another human being.
Our brains often convince us that strangers don't want to be interrupted, yet research from University of Chicago psychologist Nicholas Epley and others consistently shows that we systematically underestimate how much other people enjoy brief conversations with strangers. We expect awkwardness; they often experience connection.
Most people aren't waiting for the perfect opening line. They're waiting for someone else to be brave first.
That someone can be you. That someone should be you.
Build Your Portfolio One Conversation at a Time
Social wealth isn't built in dramatic moments.
It grows through repeated, ordinary interactions that gradually expand the number of people who know your name and whose names you know in return. Some of today's strangers will become tomorrow's acquaintances. A handful of those acquaintances will become friends. A precious few will eventually become the people you can't imagine life without.
But none of that happens unless someone starts the first conversation. The next person you meet doesn't need to become your best friend. They simply need to stop being a stranger.
This Week's Connection Challenge
Before next week's newsletter arrives, challenge yourself to start four conversations with people you don't already know.
Practice each of the four approaches once:
Begin with an observation followed by a question.
Ask someone for their advice or professional opinion.
Become curious about the story behind something they're wearing or carrying.
Simply introduce yourself with an honest, slightly awkward hello.
Don't measure success by how long the conversation lasts or whether you exchange contact information.
Measure success by one thing alone: you turned a stranger into an acquaintance.
That's how social wealth grows. One conversation, one connection, and one courageous hello at a time.
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What’s been your best conversation starter? Do you wait the full five seconds before saying hello? Have something you think could help others? Just hit reply — your email goes straight to my inbox. 🙏
