Just imagine that you are at a house party (THE hotbed for conversational "speed dating"), do you notice that your general audience might have changed every 5 mins but your subject matter and storytelling methods might not have? As the main listener in the conversations you are involved in, do you become a little bored of yourself as a result?
Most conversational norms begin with small talk (ie. weather, your weekend, origin story), develops into discussions on the activities, but the majority of the time the conversation arc might never dive further into probing philosophical ideals or deviate into random chatter about that Powerpuff Girls episode featuring gangster amoebas.
I have come to realize that in order to satisfy my own curiosity and amuse myself (which in extension, hopefully amuses those around me), my conversational approach stems from 2 basic guidelines:
(1) Deeper understanding: Asking questions that dig further into subject matter. Also includes verifying your understanding of what has just been explained with further questions. (if subject matter is appropriate and opportunity arises, inject a few fun ones into the "further questions" portion of the Q&A).
(2) Creative explication: Varying the manner in which one explains a concept, mostly achieved by playing around with the narrative structure or adding fun word associations.
This combination of transparent curiosity and reactive playfulness is not only effective in capturing your audience but also helps keep you genuinely interested in what someone else has to say. Furthermore, the combined effect of (1) information gathering and (2) novel delivery of a concept could further goals if the participating individuals' visions are aligned. It helps develop fresh perspectives, yield collaboratively creative responses and spark new ideas as a result. Who knows where these new ideas could take us?
Nonetheless, the 2 guidelines hold conversational risks with potentially severe repercussions, especially if not practiced with care and sensitivity:
(1) Deeper Understanding => Creeper Not Understanding: Not knowing when to stop probing can quickly flip a curious mind into one that is perpetually infringing on other individual's personal space. However, it is sometimes hard to draw the line as it depends in real time on how the individual asking the questions is phrasing the questions and how the individual receiving the questions is perceiving and reacting to it. As such, there is no hard and fast rule to determine when to stop asking questions, but a usual rule of thumb is to structure your question in a transparent yet balanced manner. As you are delivering it, read the facial and gestural cues of your partner to gauge if it is ok for you to proceed.
(2) Creative Explication => Irreverent Exploitation: When one gets creative with narrative structure and word associations, one is relying heavily on intuition and the unconscious mind to guide your verbal journey. Intuition, most of the time, does not come with an inbuilt filter. Without sufficient practice or awareness of where intuition could bring you, your motor mouth could autopilot you into dangerous territory. To exercise the right of Creative Explication without causing social damage requires an individual to have had reflected heavily on important issues and to have had set defined boundaries - boundaries that are cognizant and sensitive of others' point of views.