Kontynuacja losów George'a Webbera oraz znajomości z jego muzą i kochanką, Esther Jack, która wprowadza go do wielkiego świata.

Thomas Wolfe contended that The Web and the Rock, the precursor to You Cant Go Home Again, was "not only a turning away from the books I have written in the past, but a genuine spiritual and artistic change." To demonstrate his commitment to a new literary direction, he transformed his protagonist Eugene Gant into the more mature and aware George Webber.The Web and the Rock continues Wolfe's own story through George, a young writer whose works resemble Wolfe's own. The first half of this posthumously published novel describes George's evolution from small-town southern boy to struggling New York novelist and attempts to answer the brooding protagonist's question, "What is it that a young man wants?" The second half is devoted to his tempestuous affair with a sophisticated married woman. Ultimately, George, repulsed by the frivolous lifestyle of his wealthy mistress and her circle, retreats to Europe. But, once again, his idealism is shattered as Hitler rises to power in Germany. Disillusioned, George dreams of returning to the South of his childhood but realizes that "you can't go home again."