A dialog is two people communicating. A conversation is two people each trying to explore the knowledge and possibilities created by the presence of the other.
To be playful is not to be trivial or frivolous, or to act as if nothing of consequence will happen. On the contrary, when we are playful with one another, we relate as free persons, and the relationship is open to surprise; everything that happens is of consequence, for seriousness is a dread of the unpredictable outcomes of open possibility. To be serious is to press for a specified conclusion. To be playful is to allow for unlimited possibility.~ James Carse
Carse was writing about game play and physical play. His point is equally valid in conversation.
I often describe what I do as “creating conversation” but it’s important to understand that there’s nothing special about me. I’m simply experiencing my life from a first-person perspective, and so it appears to me that I’m endeavoring to “create this conversation.” Furthermore, I’m often having conversations with people who haven’t spent as much time thinking about the meta around conversations: what is a conversation, what’s a good one, how can we create them, etc. That reinforces the illusion that I’m “creating this conversation.”
Carse’s point reminds me that a conversation is created by both people (or however many there are, of course). When I approach conversation from a mindset of being playful, I’m less likely to do all the things which make for a bad conversation. (Do you really want me to list those? …perhaps another day.)
His point suggests that if I want to play, I should do everything I can to create a space where playful conversation can appear. I can prepare by some research, but I could also dedicate time directly beforehand where I think of nothing but the person and the upcoming conversation. I can do generic “make them comfortable” things, but I could also strive to be the conversation partner they’d play best with.
In both play and conversation something will eventually end the fun; there’s an endless array of things that will put a limit on duration. The topics, depth, emotion and every other aspect of a conversation are necessarily limited by things that are beyond control. So there’s nothing to be gained by approaching conversations in ways that further limit them. We shouldn’t play to win, we should play to keep playing. We shouldn’t converse to reach a goal, we should converse to keep conversing.