Follow the 3 Ss: Be Stupid, Spontaneous, and Sporadic. Wherever your brain takes you, filter it for appropriateness: if it’s appropriate, say it regardless of how weird or strange it is (again, we assume it’s appropriate), because it will make the scene more interesting.
Stupidity is necessary because logic is boring: who wants to be told things they already know, and have things explained that they could explain themselves? When you’ve run out of new material to explore, create new material out of what you already know: be stupid. This way, you find new things to talk about, and new things the other people don’t already know and haven’t already thought about, are interesting.
Spontaneous is needed because a natural progression of the conversation is much more welcome than a forced progression, and you never know when you’ll have an inspiration for another topic. If we’re talking about cats, and you start talking about mice, people in the conversation may want to know how you got to mice. If you say it’s because cats typically chase mice and cats remind you about mice, then everyone understands how you reached the new topic, and they accept the change in conversation. If instead you say you thought of mice and want to talk about it, you are saying two things: 1. I’m here to talk about what I want to talk about, and 2. I don’t respect or care for your conversation, or your approval of conversation topics: I’m just going to introduce things selfishly. (Tip: If you do want to force a topic change, use the conversation transition “Can we talk about mice now?” If they say yes, proceed, if they say no, you are being rude by proceeding. Read about Conversation Transitions).
Sporadic makes the downtime interesting. If you are predictable, people will get used to your tangents and its effect on making the conversation more lively will diminish. If no-one knows when you’re going to say something next, then there’s suspense as a result of people’s anticipation of your comments. However, you should not hijack the conversation and just spit out a stream of random comments because, unless you’re a skilled comedian, it will stop being entertaining. Therefore, you should switch between being normal, and being a source of creativity for the conversation.
Another thing your comments do is create tension between what everyone was talking about, and the new outrageous thing you are talking about. This tension sparks compare and contrast within the minds of all its participants, which can trigger inspiration within other people’s mind, therefore progressing the conversation and engaging everyone in the conversation: the mark of a good conversation.
I like to watch talk shows like David Letterman and Craig Ferguson, who are conversational geniuses (note that Ferguson has a late night audience so he will pander towards more inappropriate humor).
Other tips are to: create scenes, create EMOTION: people like stories, and stories need emotion. Create tension randomly, then dispel it equally randomly. The three Ss’ will keep your conversations interesting, and you’ll learn the proper balance of over the top creativity and normalcy with practice.
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