Among the many spices of human life, conversation is among the zestiest. Good conversations can come in many forms. Sometimes a good conversation means that the conversationalists were able to stay focused on a specific topic and, through discussion and argument, discover some greater truth, nuance or perspective on an important issue.

By contrast, sometimes a conversation might be good, not because of its focus, but because of its lack thereof. There is great joy to be found in an eclectic, branching dialogue wherein the brain’s free associations lead to a maze of tangents and digressions that frequently result in the utterance of the words, “Wait, how did we get here?”

At other times a conversation may be good merely because of its simple casualness, such as in the easy back-and-forth of two friends catching up, whether after a few days or a few years apart, where the conversational flow and the familiar humor comes as easily as sinking into an old, comfy chair.   

Yet, despite the numerous ways in which a good conversation occurs, we all know someone (or more likely, many people) with whom a good conversation remains elusive. Indeed, with such people even routine, bland conversation can be difficult, yet alone good conversation.

This strikes me as a tragedy worth understanding. After all, conversation is that unique instance of human brains, the most sophisticated and complex isolated systems on the planet, interacting directly with one another. The failure of so many of these interactions is as disappointing and surprising as the fuse of a firework failing to ignite on the Fourth of July.

  A simple diagnosis of this issue would be to say that some people are just boring or dull and there are always bound to be a few duds. Such a view is too simplistic. From personal experience, I have had delightful conversations with very dumb people and have found it nearly impossible to get more than two sentences out of very smart people. I follow politics extensively, but often become bored when other people talk politics. By contrast, I don’t care at all about sports, but occasionally I’ll find someone else’s sports talk engaging. Bizarre, huh?

Clearly, single intuitive predictors of what’s likely to make for a good conversation are insufficient. Instead, I would propose five main traits that conversationalists have to varying extents: intellectual dynamism, overlapping interests, familiarity with the other person(s), personality and sincere curiosity. The extent to which someone is likely to be a good conversationalist depends upon their status for each of these five traits in relation to the person they will be conversing with. Naturally this list is not exhaustive, but I’m not writing a dissertation here.

What is important is the interplay of these five traits, how deficiency in one area can be compensated by proficiency in another and how that compensation shapes the conversation. Moreover, some of these traits are linked to one another. For example, familiarity naturally increases over time and, along with it, overlap of interests increases as two people come to know what they have in common.

The encouraging thing about this framework of conversational potential is that it provides the ability to diagnose, in terms of both their traits and your own, why conversations with certain people my be dissatisfying. For example, I have a friend that isn’t especially curious about politics but is quite smart when it comes to sports, and I know that my personality can get condescending when I talk about politics. With this friend, then, maybe it makes sense to ask questions about the scientific elements of sports that I find interesting or to broach politics through the lens of Spurs’ coach Gregg Popovich’s statements about Trump.  

Of course, truly great conversations are still much more likely to occur between two people who are proficient across all five traits while some people genuinely are hopeless dullards. I once sat next to a guy in a high school class and, after a year, I had become convinced that his sole ability was to recount the previous night’s football games on a play-by-play basis. Familiarity only goes so far.

True, in most cases a categorically rigorous analysis isn’t necessary to figure out how to improve a conversation, because most people are decently functional human beings. However, I’d hope my proposed five-trait theory can be useful where it is most needed: situations where conversation becomes less a smooth exchange of thoughts rather than a mutual pulling of teeth.