Sam Lipsyte’s The Ask is a darkly funny examination of parenthood, disenchantment and the emptiness of corporate profession in contemporary America. A world of cell-phones, cynicism, and pill-popping becomes the landscape of modern child-rearing in Lipsyte’s 2010 novel.
Milo Burke, married and nearing the age of forty, works in the development office of a mediocre university in New York City. His job is to secure donors and donations for the university's art department. He is not good at his job. A father of a four-year-old son, Milo is a failed artist, mired in daydreams and bitterness and well aware of the flaws in his personality.
The book’s title is derived from the parlance of Milo’s development work which, like the novel, is riddled with specialized, absurd, and politically shaped language. An “ask” is a potential donor or a potential, targeted donation. Milo Burke’s job is to turn the “ask” into a “give,” something he does extremely poorly.
In a dialogue-heavy, first-person narrative, Milo is often self-denigrating, ironic and self-aware, but ultimately cannot overcome the faults and flaws that he sees in himself. Though he is sharp-witted, funny and verbally quite talented, Milo is driven to destructive habits, taking his wife’s pain medication and indulging in binge drinking at inopportune moments. A person of well-developed critical abilities, Milo is apparently morally incapable of reaching his potential and achieving success.
The story of the ask picks up when Milo is fired from his job in the development office, then called back in for one last "ask." An old college friend, Purdy, has contacted the university about a potential “give” and requests Milo Burke be put on the case. Purdy’s reasons for selecting Milo serve to motivate much of the novel's action.
Purdy comes from a wealthy family but presents himself as a self-made man: fit, enterprising, intelligent and jet-setting. Set apart from everything that might be called “average,” he is the opposite of Milo Burke. The clean surface Purdy presents covers up a secret from his past. This secret is the reason he calls on Milo for help.
A long-standing, secret relationship with a poor woman from his college days results in a child who eventually enlists in the armed services, goes to the Middle East, and suffers the loss of his two legs. This injured son, Don Charboneau, is embittered, violent and addicted to drugs. When he returns to the United States and tracks down Purdy, Milo’s job is to find a way to either calm Don down or find out how much money will be needed to pay him off and get rid of him.
The novel follows Milo’s attempts to make this “ask” work so that he might win his job back. Dealing with Don is only half of Milo’s story. Fatherhood and marriage are also principle elements of the story in The Ask.
Milo and his wife Maura share parenting duties and live in a static marriage, full of discussion but lacking disclosure. Recollections of their early relationship crop up through the novel as well as Milo’s memories of his life at college, where he believed he would one day be a great artist. Making ends meet and raising Bernie, their four-year-old son, Milo reflects often on his former dreams and how far he has fallen short.
In retrospect, Milo recognizes the petty competitions that fueled him in college, the stereotypical, false hope of being not only better than his peers, but being the savior of modern painting. When Milo meets his college friends again, through Purdy, his lack of progress in adulthood becomes clear. Professionally and emotionally, Milo has not recovered from his lost dreams to become a painter despite the fact that he has long realized the dream will never come true.
Milo’s disillusionment is contrasted to the joyous effervescence of his son Bernie, a verbally gifted toddler who trusts and loves with great simplicity, while asking question after question about what certain words mean.
(The entire section is 1,204 words.)