John Ziegler, who is a talk-radio host of unflagging industry, broad general knowledge, mordant wit, and extreme conviction, makes a particular speci… - David Foster Wallace

Suppose I were to give you a key ring [...] with a hundred keys, and I were to tell you that one of these keys will unlock it, this door we're imagining opening in onto all you want to be, as a player. How many of the keys would you be willing to try?'
[...]
'Well I'd try every darn one,' Rader tells Lyle.
[...]
'Then you are willing to make mistakes, you see. You are saying you will accept 99% error. The paralyzed perfectionist you say you are would stand there before that door. Jingling the keys. Afraid to try the first key.

"In school I ended up writing three different papers on "The Castaway" section of Moby-Dick, the chapter where the cabin boy Pip falls overboard and is driven mad by the empty immensity of what he finds himself floating in. And when I teach school now I always teach Crane's horrific "The Open Boat," and get all bent out of shape when the kids find the story dull or jaunty-adventurish: I want them to feel the same marrow-level dread of the oceanic I've always felt, the intuition of the sea as primordial nada, bottomless, depths inhabited by cackling tooth-studded things rising toward you at the rate a feather falls."

Do you suppose it's so much easier to make conversation with someone you already know well than with someone you don't know at all primarily because of all the previously exchanged information and shared experiences between two people who know each other well, or because maybe it's only with people we already know well and know know us well that we don't go through the awkward mental process of subjecting everything we think of saying or bringing up as a topic of light conversation to a self-conscious critical analysis and evaluation that manages to make anything we think of proposing to say the other person seem dull or stupid or banal or on the other hand maybe overly intimate or tension-producing?