
Recently at a large social gathering, a techy friend of mine, who had been sitting next to a total stranger, said to me after their lengthy conversation was over, “That was the deepest conversation I’ve had with anybody in years. Usually, my conversations with others are superficial and don’t mean a thing.” When I asked him what they talked about, he said, “Religion. We had different views on religion, but the conversation was intimate and respectful. We were able to be honest and disagree without being offensive in any way. It was amazing.”
With many young people addicted to their cellphones, I wonder how they will learn to converse deeply with others—a necessary skill in developing intimate friendships and romantic relationships. Because a great conversation is like a beautifully-choreographed dance with both partners skillfully contributing to its beauty, a great conversation is a work of art—a function of timing, respect, and mutuality. A conversation is not an interview, a lecture, or a monologue, but a dialogue–an exchange of ideas and opinions between involved participants!
How do we learn to converse skillfully? With lots of practice! We need to be fully engaged and attentive to the nonverbal cues of the other person. We need to notice whether the other person is involved in the conversation and when to interject our own story or perspective. As with all skills, it requires lots of practice and observational data about how it’s going, that is, when it’s going well or instead grinding to a halt and in need of radical repair.
I remember vividly the awkwardness of my first date when I was 16. There were long silences because neither of us was comfortable conversing. Because long silences made me more uncomfortable and I couldn’t think of anything to say, I began reading the street and store signs we passed as we drove around the city. “Oh, there’s State Street!” And then several minutes later, I might say: “There’s Woolworth’s right across the street.” My sign-reading led nowhere except to more silence. Fortunately, my conversational skills improved over time.
Vital Conversational Skills
What did I learn? I learned to balance questions about the other person’s story with related comments about my own experience. When interested in another person, I learned to begin a conversation with a comment about something we had in common, even something as mundane as the weather. An interaction beginning with “It’s pretty chilly today!” could be followed by the other person saying: “My frisky companion and I nearly froze!” This could lead to: “Sounds like your dog is a loyal companion even on cold days” (empathic response communicating understanding) followed by “What kind of dog do you have?” (a question indicating interest that facilitates the flow of conversation).
An observation about the other person’s suitcase: “It looks like you’re headed for a trip” could easily lead to a brief interchange about vacations. Or a positive comment about the other person’s jewelry or clothing might wind up being a discussion about apparel or culture.
At a conference, in a classroom, or in a long line, comments to a stranger or acquaintance about a shared experience, e.g., “This instructor has a fascinating resume” or “It seems Target is always crowded,” are good starting points for a conversation. Following such introductory comments, empathic responses, open-ended or closed questions, and/or related anecdotes are generally good follow-up strategies that keep a conversation going.
If a person seems disinterested (she may be struggling with a personal problem), an open-ended question might engage her. Otherwise, the conversation could be ended politely with a brief remark: “I better get going”.
Common Mistakes
While the conversation might begin well, there is no guarantee it will proceed easily from that point on. The most common mistakes in unsatisfying conversational attempts are one member’s talking too much, getting too personal too quickly, and/or ignoring the fact that the other person is disinterested. Pursuing a one-sided conversation by adding too many details is likely to be boring to the listener. And not pausing to let the other person into the conversation is discourteous. The quiet member is often resentful about the speaker’s usurping the attentional space but is uncomfortable in saying so. Often, the quiet member is eager to leave the scene and makes up some excuse for ending the conversation.
On the other hand, shy or inhibited people often have a hard time coming up with related experiences or anecdotes that contribute to the conversation. They may be skilled at empathic responding or questioning, but uncomfortable sharing their own opinions and when they do, they offer too few details to be engaging. Responding to most queries with “Fine” or “It’s interesting,” they make it difficult for the other person to pursue conversationally such blind alleys. For shy people to develop more comfort in sharing personal information, they could start by offering their opinions about less sensitive topics, such as movies, podcasts, restaurants, sports, TV shows, or work, before venturing into more personal areas.
Recently, I observed a man bombarding a doorman with a lengthy story. The doorman, who was trapped behind a desk, looked very bored and distracted as the speaker went on and on, detailing many specifics about the event he was relating. Finally, the doorman abruptly said, “Have a nice day!” before turning away to attend to his duties. It was obvious that the doorman was not interested in what the speaker had to say and the speaker was oblivious to the doorman’s disinterest. Paying attention to the other person’s involvement in the conversation is important in having reciprocal conversations that are gratifying to both parties.
In addition, getting too personal too early in a conversation can be unsettling for the listener because he doesn’t have enough information to assess the seriousness of the speaker’s anxiety, loneliness or dysfunctional family.
Why Conversations Matter
People often wonder whether conversations, especially with strangers, are worth the risk. Because the world at large often feels threatening, we ensconce ourselves in little bubbles of connection that have a limited variety of contacts. We talk mainly to familiar types–people who resemble us in appearance, cultural background, and values, thereby depriving ourselves of the challenges that come with very different experiences.
While talking more personally to acquaintances, co-workers, and fellow club members could lead to rejection, hostility, or unwanted propositions occasionally, conversations with others can enrich our lives significantly. Conversations can provide much information about one’s neighborhood, workplace, and other local activities, while deepening our understanding of people at the same time. They can reduce loneliness, strengthen our network of connections, and expand our worldview by including others different from us. In other words conversational acuity is a skill worth developing and an antidote to depression, isolation, and polarization.

