The Art of Small Talk: How to Connect With Strangers and Acquaintances

Does small talk really matter?

Absolutely, says Shasta Nelson, social relationships expert, speaker and author of The Business of Friendship, Friendships Don’t Just Happen: The Guide to Creating a Meaningful Circle of Girlfriends and Frientimacy: How to Deepen Friendships for Lifelong Health and Happiness. 

“Almost every relationship we have starts with seemingly mundane moments,” explains Nelson. “For most of us, if we look at our best friends and the people we’re closest to, we could probably say, ‘It started with this moment.’”

To illustrate this, Nelson points to her “moment” 20 years ago, when a seemingly ordinary conversation sparked a decades-long connection. Nelson initiated a conversation with a woman by asking about her career as a life coach.

Shasta Nelson’s genuine interest in the woman’s profession unveiled a person skilled in deep conversations. This small talk encounter eventually led to Nelson inviting the woman into a book club and forming a deep friendship that has lasted for decades. Nelson suggests “reverse engineering” your own connections, and you’ll likely recognize the transformative power of seemingly mundane initial conversations. 

Of course, not every small talk encounter needs to lead to friendship. Sometimes, it could lead to nothing more than a delightful interaction. Other times, it can lead to a significant connection. Guess what? Both are beneficial.

“Have an open mind, knowing this could go somewhere, or this could go nowhere,” Nelson suggests. “But just be present in the moment and enjoy whatever it is.”

So, how can you improve your small talk skills? And how can you build more profound connections with people you meet in your daily life? Here, Nelson shares the secret sauce for mastering the art of small talk.

Rather than idle chitchat, think of small talk as the gateway to building connections. 

“Small talk is the first step of every relationship,” Nelson points out. “There’s no way to get to the deep relationships we want without starting somewhere.” It might feel trivial or awkward in the beginning, but if you want meaningful relationships, you need to be willing to begin them. And that’s where small talk comes into play. 

To strike a balance between disclosing enough personal information and avoiding oversharing when mastering the art of small talk, Nelson suggests aiming for incremental sharing. When you start revealing, give a little bit and then stop, gauge interest and check in. 

“Are they sharing? Are they giving warm cues? Are they engaged? We don’t ever want to get in a situation where we’re on a monologue,” she points out. “It’s kind of like putting a fishing line out and seeing if there’s a little tug there.” These initial conversations—where you’re getting to know someone and slowly building trust—involve mutuality, a back-and-forth sharing of small tidbits of personal information. This ensures a balanced exchange and fosters a gradual, comfortable progression into deeper conversations.

How can you tell if you should share more, regardless of whether the interaction is going somewhere or if you’re never going to see each other again? “You don’t need to know where this is going—and that’s okay,” reminds Nelson. “If this person never becomes a best friend, it can still be a magical moment.” 

She gives the example of talking with someone on an airplane. Though you might never see this person again, it could be a life-changing conversation. The same holds true for briefly chatting with a neighbor. You don’t need to become best buds or even make these chats a daily thing—it’s just a moment of connection. “Let go of needing to know what the outcome is,” she advises. Instead, relish the present moment’s potential, recognizing that even brief interactions can be worthwhile.

During interactions, look for signs that small talk might evolve into deeper relationships. Indicators of warmth (smiling, positive verbal cues) and interest (active listening, eye contact) provide telltale verbal and nonverbal cues that you’re having a positive interaction. 

Nelson suggests dissecting past conversations to identify these positive elements, such as giving compliments or asking follow-up questions, that contribute to feeling good afterward. By consciously incorporating positive elements into your interactions, you can foster more remarkable connections and create opportunities for relationships to evolve positively.

However, Nelson notes this might look different for everyone—and the context of the situation plays a role. For instance, if someone doesn’t show warmth, that doesn’t necessarily mean they’re not interested—they could just be in a hurry or distracted. 

That’s why Nelson emphasizes the importance of gauging feelings during interactions when learning how to master the art of small talk. “Did that person show interest in me and make me feel seen and liked for a moment?” she says. “We all want to walk away feeling pleasant, which means we enjoyed that interaction. One of the biggest predictors of who we’ll end up bonding with is how we feel when we’re in their presence.”

If you’d like to move beyond surface-level topics, Nelson offers solid strategies. “Ask open-ended questions and show with your body language that you’re interested in the answer,” she advises. That could mean smiling, eye contact and an affirmative nod.

Not sure what to ask? Start with whatever shared context you have in the moment. Nelson recommends using simple observations or compliments, which create an opportunity for the other person to share. For instance, when you’re walking by your neighbor in their front yard, complimenting the landscaping and asking about their gardening interest opens avenues for more in-depth conversation. When you pass someone walking her dog at the local park, you can start the conversation thread around that shared context—being at the park, owning a dog, etc.

“You can just give people that thread, start pulling and then from there, it might develop,” she notes. “But I think a lot of us have a hard time starting that thread.”

If you’re shy, you might struggle to initiate conversations. Nelson acknowledges that, while you might never feel at ease, you can set realistic expectations and value the outcome of connection over the discomfort of initiating chats. 

Remember, you already do a lot of things in life because you want the outcome. You wash the dishes because you want a clean kitchen. You work out because you want to feel healthy.

“Working backward, it might be, ‘I want to feel more connected or less lonely. I want to feel more belonging in my neighborhood or like I know my coworkers better.’ There’s no way to do that without starting to connect,” she advises.

To leave a conversation with ease, Nelson suggests a three-step approach. Begin with an affirmation or kindness, expressing appreciation for the interaction. Then, smoothly transition by stating what you need to do. Finally, wish them well, maintaining a positive tone. 

For instance, thank them for the interesting conversation at a party, then explain your intent to mingle with others before you leave. This strategy allows for a polite, comfortable departure, emphasizing gratitude and good wishes as you smoothly extract yourself.

Shasta Nelson concludes that there’s no shortcut to feeling familiar and comfortable with someone, except to go through unfamiliar conversations and uncomfortable ways to get there. “Most of us feel worried about rejection or being judged. Most of us have anxiety around interacting. And almost no one loves meeting people and being in unfamiliar and uncomfortable situations. 

But there’s no way to build more meaningful relationships down the road without starting that dance,” she acknowledges. “So, give yourself a pep talk, have extra compassion for yourself and just allow yourself to be imperfect at it.”

Photo by Robert Kneschke/Shutterstock.com