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The story of the five-day interview between Rolling Stone reporter David Lipsky and acclaimed novelist David Foster Wallace, which took place right after the 1996 publication of Wallace's groundbreaking epic novel, 'Infinite Jest.'

Astor William Stevenson is on the verge of a big step in his career, but when his girlfriend leaves him, insecurities surface and he transforms into a wrecking ball on a stream of darkly comedic dates and misguided romantic pursuits.