
The silence was unbearable. My parents and I exchanged glances with my chemistry teacher and his wife across the room. We exchanged polite, forced smiles, typical of northern white Protestant interactions. We were at a loss for words. I promised myself that as an adult, I would never endure such awkward exchanges.
I couldn’t have been more mistaken. Only those who are rude or overly assertive can navigate life without stumbling into the occasional awkward or stilted conversation. Over time, I’ve discovered three strategies to breathe life into a faltering conversation when walking away isn’t an option.
Engage with thoughtful questions
I’m acquainted with a well-known podcast host. His job involves interviewing people, including those who might initially seem uninteresting. Yet, he always uncovers something fascinating to explore. This skill translates to his everyday interactions: he listens carefully, picks up on the slightest hint of intrigue, and probes further.
Relying solely on this technique can make a conversation feel like an interrogation. I’ve been in situations where I was bombarded with questions, and the other person didn’t offer any openings for me to reciprocate. To avoid this, intersperse your questions with:
Provide more detailed responses than required
While questions propel a conversation forward, sharing your own thoughts allows it to flow naturally. Respond to someone’s answer with your perspective, highlight areas of agreement, or gently express disagreement. Explore a related tangent to keep the dialogue engaging.
A frequent error is responding too literally: “Where are you from?” “Rochester, upstate.” Remember, you’re not completing a survey—you’re engaging in conversation. Add depth: “Actually, I’m from a small town south of Rochester with just one traffic light. It’s called Lima, like the bean. They even hosted a lima bean festival!”
You can vary your responses each time. I don’t want to discuss lima beans in every conversation. Sometimes I bring up the local bar famous for having “the world’s largest urinal,” other times I talk about my small K-12 Baptist school, my favorite coffee shops in Rochester, or how my neighbors included a historic one-room schoolhouse and a cornfield.
Alternatively, I shift the conversation to San Francisco, where I spent three transformative years and still deeply miss. No one minds that I don’t stick to the exact question because we’re not in a formal setting—we’re in a quirky surf bar in Hell’s Kitchen.
Be prepared to shift topics
In fact, I completely fumbled a conversation in that surf bar just last week. Four of us were discussing New York neighborhoods and their gentrification. We’d name a neighborhood, mention a few changes, agree on the city’s overall gentrification, and repeat. It’s a common New York discussion, but we eventually ran out of steam because we forgot to prepare a topic shift.
A pivot is a smooth transition to a new subject, not a random leap to an unrelated topic. While leaps can work occasionally, they can come across as desperate with people you don’t know well. It’s better to build on something previously mentioned in the conversation.
This is where detailed responses truly shine. If someone elaborates beyond a couple of sentences, you should mentally note a detail to revisit later or use as a springboard for a new story, steering the conversation in a fresh direction. That’s why I often shift from discussing Lima and Rochester to the more vibrant San Francisco, where countless topics await exploration. (Or, of course, another round of gentrification talk.)
Pivoting based on someone else’s input is more effective than steering the conversation with your own anecdotes. I tend to ramble, digress, and then circle back to my tangents. If you only pivot from your own points, even if you let the other person speak, you risk dominating the conversation’s flow. When pivoting, try to do so selflessly, building on what others have shared.
Never forget: Everyone has something fascinating to share. Small talk only feels dull until you uncover that unique spark.
