The Hidden Mechanics of Conversation

What awkward conversations taught me about curiosity, value, and the adventures hidden within ordinary people.

A Question About Conversation

Have you ever wondered why it is harder to talk to some people rather than others? Why is it that some conversations seem awkward while others don’t? Is it because of the people you are talking to, or maybe the topic of your conversation?

This has always been a mystery to me. The feeling that naturally arises from this is that I must be doing something wrong. Some people can have great conversations with nearly everyone they meet, while only a select few of my conversations don’t end with me finding a way out because they are getting awkward.

I have set out to uncover what lies beneath the conversations that are the most enjoyable, and what is happening in the ones that aren’t. For the sake of respect and privacy, I won’t be using real names or places in this article.

Two Conversations That Didn’t Make Sense

There is one person whom I see frequently, with whom I try to avoid conversation by all means. Yes, this may seem mean, but we naturally gravitate towards those with whom we have much in common. I like the person, but I don’t always like the things we talk about in our conversations. This leads to avoidance. However, when we are talking, the awkward feeling I spoke of does not exist in a place that I expected it to. Although I find little interest in what is being said, there is an unexplainable satisfaction after the conversation.

There is another person to whom I speak frequently. This person and I have a lot in common. We discuss things that are interesting and have similar views on the topics. Before long, the conversation becomes awkward, and I am grasping for a way out. This is a place where I do not expect awkwardness to exist, yet it does!

To understand what is going on under the surface in these conversations, I examined the conversations that were enjoyable to me. I wanted to understand who these people were and what made their conversations enjoyable. Upon understanding this, I wanted to find principles that could apply to future conversations that would make them enjoyable for both parties. This would lead to connections with people I may not have previously connected with.

The Conversation I Didn’t Want to End

Let’s look at an enjoyable conversation I had recently.

This conversation started with me introducing a topic that I had been considering recently. I wanted an honest opinion on what this person thought about it. I mentioned my theory, and the person appeared to light up at it. The person paused as though the question deserved consideration. The person then began speaking aloud to test the theory against what they knew. This process seemed to bring excitement to them. Then followed a well-considered response. I examined this response and asked another question, excited to dive deeper. As the conversation continued, excitement continued to grow. Curiosity was shining through the window. The depths of what we could uncover appeared endless.

Someone interrupted the conversation.

I was sad.

There was more road to travel that would now remain in the shadows.

The adventure was over.

The Conversation That Never Began

I had this same conversation with another person. I introduced my topic in the same way and handed the conversation over. This person quickly thought about it and spouted the first answer that came to mind. The response seemed insufficient. There was no joy, no excitement. The next words from this person changed the subject. The adventure was over before it had even begun. I felt like I had just changed into my trunks to go swimming, and this person told me it was already time to leave. In a way, it hurt. This topic was important to me, yet deemed no consideration on their part.

The latter conversation, however, was not awkward but unenjoyable. I would like to examine the mechanics of an awkward conversation before making sense of it all.

An Experiment

This awkward conversation was with someone I was meeting for the first time. Although I did not know the person, I heard a lot about them from mutual acquaintances. The conversation began with the usual small-talk. After the first minute or two, the conversation turned in an awkward direction. There was a lack of comfort, an invisible wall between us. The conversation became challenging. I did not know what else to say.

There was also a problem. We were stuck in the same place. The event would not be over for a few hours.

Then came an awareness of the situation at hand.

I have considered this topic before.

This would be a perfect time to experiment.

I introduced a topic that I knew they were familiar with. A topic that I heard this person might have powerful feelings about. I made myself vulnerable, presenting my views.

With the wrong person, these views might self-destruct. With the right person, they would create a rapport to the very core of their existence.

Before I realized it, we had been talking for hours, and now it was time to go. We had traveled down many roads in these discussions, one topic leading to another. A friendship was forged through these conversational adventures.

What started as awkward turned profitable and enjoyable.

The Adventure

What do we learn from these scenarios?

There must be a connection.

At first, they all seem random. Different people, different places.

As I examined the patterns, the thread connecting them all emerged.

The word that continues to cross my mind is adventure.

Recently, I discovered that someone I know and I have a mutual friend. Rather than talking about who they were, we shared the unique situations we had each experienced with this person. Suddenly, our old adventures had become a new one.

The people I look forward to speaking with the most are the ones with whom we have shared these kinds of experiences.

The first person mentioned, the one whom I try to avoid, is willing to embark on an adventure. The reason I avoid this person seems to be that I don’t find the adventures interesting. However, during the discussion, the person is comfortable, open, and real! Although I don’t find their adventure exciting, they do.

This changes the mechanics.

I hung around to see what happened.

The second person, a skilled conversationalist, found my adventure exciting and was willing to travel down the road to see where it went. It felt like they found this adventure as important as I did. They had a hunger to understand what it all meant. I felt as though this person understood me.

I remember as a child, my grandmother and mother would always bring me along to take my great-grandmother shopping. This was not an adventure I wanted to take, and I could not understand why I needed to be there. I found little value, little excitement. I would avoid it next time if possible.

However, one time my grandmother mentioned she would buy me a video game. This game was important to me. I could not wait to be picked up for this adventure. I was excited to take it. There was great value. I was present in a way that I had not been the previous time.

Consider the third person with whom I shared my important interests, who gave a quick answer and moved on. I believe this person found little value in a concept that was important to me. Not only did the person not find value, but they shut down the adventure before it started. Not only did they not want to take part in the adventure, they would not even consider my adventure as something exciting or worth listening to.

Finally, the fourth person, who started awkwardly, ended up teaching me the most.

It taught me it’s possible to redeem an awkward-feeling conversation and what it takes to do so.

The Value I Had Been Missing

As I reflect on everything, I want to unmask some gems that I have mined along the way.

The first is the value. How have I been so naïve to leave value on the table by attempting to avoid conversations with people? It reminds me of a quote from Galileo.

“I have never met a man so ignorant that I could not learn something from him.”
— Galileo Galilei

It turns out I was the ignorant one in this scenario. Not only was there something available that I could learn from this person, but I found nothing worth learning from this person.

I lacked the initiative to determine how I might learn from this person, and also how to direct the conversation to that topic.

How foolish? I have been missing value for years.

Chances are, the knowledge I could gain from this person is the very thing they enjoy talking about. An adventure profitable to both parties. An enjoyable conversation.

Better yet, how often am I the one who shuts down the adventure before it starts, making what’s important to others feel worthless? It makes me wonder why some people continue to present me with opportunities to travel with them.

How did I not understand the value of spending time with my family on the way to my great grandmothers? Time that is unavailable today! I saw value in something so small, something that has no meaning anymore.

I am convinced that the people who excel in conversation understand the value each person holds. They are good at listening. They make people feel important. Their curiosity takes them on adventures many have shut down.

Maybe I have been the awkward one. Maybe, just maybe, the awkward conversations result from how I have listened to what’s important to others.