I used to have a very pluralist, relativist view about a great many social norms, including conversations, i.e. some people just prefer small talk; who am I to say that deep conversations are better? Some people just prefer to socialize in large party situations; who am I to say that one-on-one talking--which I also prefer--is better?
But I think deep, memorable conversations are too rare, and will always be in short supply. For one, it seems that we rarely invest enough time or effort in friendships for them to develop to the point where we are familiar enough with each other's interests to guide the conversation accordingly. Without really knowing someone, it is very easy for one to talk too much about something that bores or offends the other; fearing this, they may err on the side of remaining too inhibited and cautious.
Yet familiarity also breeds, if not contempt, then at least, various pitfalls that can preclude deep conversations. Repeated conversations with a person creates a repertoire of "safe topics" that the conversation partners tend to return to. No doubt these topics can be quite interesting; however, they lack surprise. The other person stops being a source of wonderment and becomes more a source of validation, entertainment, information, etc. The conversation ceases to be an opportunity for two people to grow, and more like a transaction, or even a tedious obligation. Perhaps this is a result of familiarity that serial daters know all too well.
So a deep conversation is a bit like a flower that only grows in just the right conditions. One can try to encourage its growth without making a value judgment about its beauty relative to more common flowers. Surely we would not want to live in a world where the only way to socialize was through conversation, no matter how enjoyable they were, just as we would not want to live in a world where large parties are the only place to meet people. In this world where deep conversation is rare, we should aim to encourage its proliferation. And that is impossible to do without understanding at least some of the characteristics of deep conversation.
Most importantly, a deep conversation is ripe with relevance for both partners. In many of the memorable conversations I've had, there were many moments in which I, as the listener, would say to myself, "That reminds me of _______." If I then verbalized that thought, hopefully it would strike the other person as an interesting extension of what they were saying. More importantly, it demonstrates that I was truly listening. If, on the other hand, they viewed it as an unrelated tangent, they might become frustrated at not being truly listened to.
In a certain snippet of conversation, there may be many things that are evocative enough to provoke an enthusiastic response from the listener. I will call these "hooks." For example, in the second paragraph of this post, I say:
I used to have a very pluralist, relativist view about a great many social norms, including conversations, i.e. some people just prefer small talk; who am I to say that deep conversations are better? Some people just prefer to socialize in large party situations; who am I to say that one-on-one talking--which I also prefer--is better?If I said this in a conversation, an interested listener would see at least one very compelling hook that allows them to enter with a valuable response. Perhaps they will latch onto the phrase "I used to have a very pluralist, relativist view." What caused you to change your mind? Or maybe they will challenge my position, or agree and provide an example from their own life. All of these are possibilities that may differ in their interestingness, but they are the fuel of good conversations.
I think it is useful to think in terms of conversations as a series of "hooks" that can be latched onto, because it enables you to be a better conversationalist. A listener who is actively digesting every word of every sentence is bound to find something interesting to expand upon.
"Hooks" can be thought of on multiple levels as well. A listener can ask about a single word, or a story, or the general theme of the entire conversation so far. One of my favorite things to do is to introduce a meta-conversation into the conversation. I can comment about how I feel when I'm talking to that person, or analyze both of our speaking patterns e.g. we are mirroring each other's gestures.
This can be quite uncomfortable for some people! Where it might satisfy my need to analyze everything, it might make them self-conscious. Some topics of conversation will never be interesting to some people, no matter how skilled the conversationalist is. In that sense, a rewarding conversation is partly a function of well-matched people, and partly a function of skill and effort.
But most people seem to think of conversations as solely a function of matching. If someone bores me, it must be because we don't share similar interests. It might not occur to me that I am a bad listener, that I can't recognize enough "hooks" in the conversation. Conversely, if I seem to be boring others, then they must not "get it." It usually does not occur to me that perhaps I should work on my story-telling, my jokes, or my delivery.
In the end, however, I think that the most important way we can cultivate deep conversation is to make it a priority. The excuse, "I haven't had the time" is often a way of saying "I haven't made it a priority." It is important, also, to recognize the difference between small talk and deep conversation. Even if we've talked with someone recently, it doesn't mean we've really connected with them on a meaningful level.