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.

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.'