The strength of Sam Lipsyte’s third nov­el, The Ask, is the narrator’s brand of cyn­i­cism that enlarges and coheres the snick­er­ing jokes intoned by New York­ers and New York­er sub­scribers all over Amer­i­ca. Milo, the con­di­tion­al­ly re-employed devel­op­ment offi­cer, skew­ers the fibers of urban pro­fes­sion­al life— Whole Foods, gen­tri­fy­ing neigh­bor­hoods that resem­ble the UN, blog­ging. The book moves quick­ly, pulling the read­er in with laugh out loud insights, but at times the plot is weak, even as Lip­syte incor­po­rates themes of fate, father­hood, and love. Recur­ring tropes include Jew­ish jokes and het­ero­sex­u­al male desire for all female characters. 

Lip­syte is clever with lan­guage; The Ask is pep­pered with his sig­na­ture looped seman­tic phras­es that seem to embody his world out­look— that our pen­chant for mer­ry­mak­ing, irony, and mean­ing-seek­ing is ulti­mate­ly a joke on us, a trap we weave for our TV-weak­ened souls. ​“I was tired of the seman­tic eva­sions, mine includ­ed,” he writes. His way with words reaps rewards: ​“The box score stayed in my wal­let, or the wal­let of my heart, so to speak, a smeared and origamied scrap to remind me how lit­tle I resem­bled the man I fig­ured for the secret chief of my sev­er­al selves.” 

The down­ward spi­ral of Milo’s life sug­gests that humor and seman­tic eva­sions offer no real hope, just chuck­les. The com­e­dy cuts through the col­lage of unset­tling and triv­ial expe­ri­ences that com­prise our shared expe­ri­ences, and gives shape to it, and to us.