Writing dialogue is hard

I've come to appreciate lately how difficult it is to write good dialogue. Despite how much we talk on a daily basis, somehow capturing the authenticity of conversation on paper is difficult, in part because the act of writing conversation is imbued with a purpose that conversation itself in its routine idleness and aimlessness does not possess.

In Thomas Wolfe's I Am Charlotte Simmons, his tome about modern-day debauchery at America's finest universities some of the dialogue borders on the implausible. The book has been criticized for depicting some characters as hopless cardboard figures, particularly the prep school alumni who are members of the most elite fraternities and sororities. This is debatable. What Wolfe most bitterly fails at, in my view, is depicting his more thoughtful characters. The intellectually curious students with whom Charlotte strikes up a rapport broadcast an unrealistic self-awareness to a point that seems utterly contrived. Take this conversation, where Adam Gellin, the student athlete tutor and college journalist who crushes on Charlotte, explains the M.O. of the intellectual members of his generation with dubious grandiloquence:

[...] Students like us used to just go to graduate school and become college teachers. But after that, a new type of intellectual comes on the scene: the bad ass. The bad-ass is sort of a rogue intellectual. A bad-ass doesn't want to do anything so boring and low-paid and like...codified...as teaching [...] You're an intellectual, but you want to operate on a higher level. This is a new millenium, and you want to be a member of the millenial aristocracy, which is a meritocracy, but an aristo-meritocracy.

Tom Wolfe: Are you serious???