In his sad-sack way, Milo has achieved a self-knowledge that many of us never do. He knows and accepts that he'll never be a famous painter, author, musician, or simply famous. What George W.S. Trow called the "middle distance" continues to fade from American life: the social institutions that support our higher callings on a modest scale. If you didn't make it on Broadway, you could do community theater in your town. If you didn't report for the Times, you could report for the suburban gazette. More and more, it's all or nothing, celebrity or failure, fame or obscurity. Instead of finding the middle distance for our aspirations, we line up for reality shows. After his many trials, Milo does what more of us should do: make a little nest of our bitterness. Near the end of the novel, we learn that he's "not going anywhere"; he's "digging in for the long night of here."
I will stop quoting Lipsyte now and instead urge you to read his book twice. When you do, help me out with the Lipsyte question that nags at me: How useful, in the end, as a life strategy, is wallowing in bitterness? Should we strive to move beyond it, or is that just more silly striving, the thing that got us into the deep end of the bitter pool to begin with? In The Ask, Lipsyte gives Milo some fleeting moments of Pyrrhic victory, but he's offered no permanent escape from loserdom. I wrote earlier that Lipsyte is kindler and gentler in this novel, but maybe it's his most cutting creation yet. He's telling us, with a friendly punch, that there are winners and losers in life.