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...

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The Ask Chapter Summaries

The Ask Chapters 1-2 Summary

The novel opens with Milo, a nearly middle-aged man who works in the development office of a less-than-prestigious university in New York City. Milo is having a lunch of turkey wraps (his favorite) with Horace, a temp who tends to wax philosophical about what’s wrong with the world. 

Milo’s job in the development office is to get "gives" from "asks." An ask refers either to a person who can provide something for the university or to the thing they can provide; a give is whatever the ask gives to the university. 

Milo notes that he deals with primarily low-level asks and gives such as used televisions and appliances. On the other end of the spectrum is Llewellyn, a world-traveling hotshot who scores multimillion-dollar gives for the university. Milo’s boss is Vargina, a no-nonsense woman who tolerates Milo and Horace’s childish interplay provided they get their work done. Vargina’s name’s close proximity to female anatomy is not an accident; her mother was a crack addict and the nurse at the hospital added the "r" to her name to spare her embarrassment. Milo finds it difficult to focus when Vargina talks to him and frequently indulges in literary-themed sexual fantasies with his buxom supervisor. 

The trouble begins when McKenzie, an entitled art student whose father is a major ask, stops by to ask an enrollment question. When Milo tries to explain that he can’t help her, she condescends to him about his low-level job and demands assistance. For reasons he cannot fully explain later, Milo tells McKenzie off and gets fired for it.

The irony of being fired for insulting the over-privileged McKenzie is that Milo himself is an artist. Although he occasionally attempts to paint at home, his efforts largely have been fruitless.

In the wake of his dismissal, Milo’s job searches have dwindled. Although he came close to being hired a few times, his prospects have dried up and now he has stopped looking; instead, he rides the subway or hangs out at a doughnut shop. 

While eating his doughnut, Milo reflects on the fact that he used to fantasize about wiping out large groups of people (via flamethrower). He acknowledges his daydreams were disturbing, but they left him during happier times, only to return now. 

After an encounter with a presumably homeless lunatic with pedophiliac designs (whom Milo dubs Kiddie Diddler), Milo receives a text from his wife, Maura. She is aware that he has given up on the job search and asks Milo to bring home some supplies for Bernie, their young son. For now Milo ignores a text from a more familiar number: that of the development office that just fired him.

The Ask Chapters 3-4 Summary

Upon returning home, Milo attempts to sneak a Vitamin Water out of the view of his young son, Bernie, who is obsessed with juice. He tells Maura that the other message he received while he was out was from his old job, asking him to come in.

As Bernie continually interrupts them (mostly with requests for Milo’s “juice” or questions about his new favorite subject, foreskins), Milo and Maura try to figure out why the office that fired him two months ago would want to see him again. Maura fears it involves legal action from McKenzie’s family.

Milo returns to the development office and finds himself in an awkward conference with Vargina and Llewellyn, the latter doing nothing to disguise his dislike for Milo. Milo returns his disdain with pointed jabs about Llewellyn’s affected Anglophile tendencies. They are soon joined by Dean Cooley (to whom Milo refers as War Crimes), an ex-military man who now heads the development office.

The three explain that a major ask specifically requested Milo and that he can win his job back if he lands the ask. The dean reveals that the ask is Purdy Stuart, an old friend of Milo’s, and leaves. Milo seems to recognize that their needing him has afforded him a small amount of power. Llewellyn further insults Milo and accuses him of leering; when Milo later attempts to apologize to Vargina for leering, she reveals that it was Horace who felt that Milo was eyeing him.

Milo recalls his college days with Purdy as he ponders why his old friend demanded him for this engagement. Purdy came from money but had made his own fortune by getting in online music and celebrity culture early in its development. Even as a young man, Purdy seemed to understand the unspoken class system in America and was keenly aware of his own place at the top of that system. He often broke up with girls if they weren’t in his league, including Constance, whom Milo later dated. In college, Purdy always seemed destined for greater things, but Milo noted his ability to be friends with a wide variety of people (including those who would become future business contacts after he left college).

Looking back, Milo notes with sad irony how all of them thought they were destined for greater things; once reality set in, Purdy was the one who emerged from the pack successfully. Milo now wonders if he knew it all along and simply humored the others.

The Ask Chapters 5-6 Summary

Milo meets Purdy for lunch at a steakhouse and decides to cash in on the experience, ordering a huge feast and downing lots of liquor. When Purdy is in the restroom, Milo even helps himself to some of Purdy’s steak and potatoes.

Once the catching-up has subsided, Purdy decides to get down to business: he is interested in doing a considerable give and Llewellyn has led him to believe that Mediocre University (as Milo calls it) is looking to step up their game. Like everything else, Purdy describes it in terms of cultural and financial cachet; in his world, everything seems to have some kind of value. He also notes Milo’s bitter, hyper-cynical attitude and chastises him for it.

Milo admits that he thinks Purdy was born into privilege and didn’t truly earn his money. Finally, Purdy reveals to the increasingly drunk Milo that his interest in the university stems from his wife. She attended the university’s art program and had a great experience (which Purdy financed, naturally).

When Milo asks why he requested him on the job, Purdy speaks vaguely about their shared history as well as some things that Purdy will need to ask of Milo at a later point. Purdy also notices that Milo ate his food and ascribes it to an overall need to grow up.

Milo blacks out and wakes up in a cab heading over the bridge to his home in Queens, with fare stuffed in his hand.

The next day finds Milo nursing a punishing hangover on his couch as his wife gets ready for work. Bernie’s school was abruptly canceled for the day, leaving his parents to arrange daycare for him. Bernie’s school is a small, art-oriented, and private one whose faculty are prone to lots of "navel-gazing retreats."

Maura asks what Milo is going to do that day, and he replies with the vaguest of explanations. Maura again seems to hint at his lack of drive before she heads off to work. Finally, Christine, Bernie’s babysitter, arrives. Milo notes that Christine’s extremely low rates for her services are indicative of the low quality of care she provides. Many of the kids in her “program” are rough around the edges, and their influence has started to rub off on Bernie.

When Milo straps Bernie into a woeful toddler seat, Christine plays The Passion of the Christ on the in-car DVD players, despite Milo’s voiced concerns.

The Ask Chapters 7-8 Summary

Milo’s first day back at his old job is jarringly surreal. He encounters Horace, who now has a much larger space in the office (including Milo’s old desk). Horace is in the middle of a sexually graphic conversation with his own mother about a significantly older woman he is dating. When Milo tries to apologize for the harassment Vargina mentioned, Horace claims he only did it as a joke.

Horace’s open relationship with his mother reminds Milo of his strained relations with his own mom. Milo was never able to understand why his mother put up with his father’s philandering and other bad behavior. To make matters worse, when his father was dying, Milo found himself at odds with his mother about the best care plan...

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The Ask Chapters 9-10 Summary

Milo races to pick up Bernie from the home of Christine, his low-rent babysitter. When he arrives at the house, he discovers that the daycare children are under the watch of Nick, Christine’s volatile brother. As Nick shoots some of the kids with Vitamin Water from a plastic gun, he asks Milo if he wants to make some money helping him build a deck. Milo, who is uneasy around Nick, vacillates, but Nick makes him promise to give him a firm answer soon.

Noticing Bernie is not among the children running around screaming, Milo heads into the house, momentarily worried that the lack of supervision could leave Bernie susceptible to a variety of deadly accidents. Instead, he finds Bernie biting the crotch of one of his...

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The Ask Chapters 11-12 Summary

A cash-strapped Milo agrees to Nick’s deck-building gig to earn some extra money. Early in the morning, Nick picks up Milo in his truck and heads out to get the lumber for the deck.

Along the way, Nick details an elaborate concept he has for a reality television show. The focus of the program would be the last meals of convicts about to be executed. Nick suspects that the practice of giving an inmate whatever he/she wants for a last meal is actually fictional. He believes they only offer food that is within a close vicinity to the prison because so many inmates choose cheap, greasy fast food for their last meal. Nick’s idea is to create a program called Dead Man Dining in which the world’s greatest chefs...

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The Ask Chapters 13-14 Summary

Inside, Milo opens the envelope and finds a considerable sum of money and a stack of correspondence between Purdy and his secret son, Don. In a lengthy email riddled with racist comments, Don unabashedly asks Purdy for money. He intimates that Purdy has no understanding of his life, particularly in the service.

In a note to Milo, Purdy asks Milo to be the courier to deliver the payments to Don. He also wants Milo to find out what Don is all about and if he has any master plan in his pseudo-blackmailing of Purdy. Purdy is terrified that his wife, Melinda, will find out about Don and realize that Purdy has been dishonest with her.

Milo laments his lack of connection with Maura, particularly the downturn in...

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The Ask Chapters 15-16 Summary

Milo heads out on his first visit to Don, Purdy’s son. When he arrives at the building, he is let in by Sasha, Don’s girlfriend. Sasha, who seems vaguely high, continually mists herself to combat the stifling heat of the apartment.

Sasha questions Milo about his involvement with Purdy and the amount of money he has brought. At times Sasha seems to be flirting with Milo, but in her altered state it isn’t fully clear.

Soon, Don arrives home and interrogates Milo about his work with his father. Don takes off his two prosthetic legs and complains of the soreness of his “humps” (the word he uses to describe the remaining parts of his legs). Don asks Milo if he knows any way to score drugs in the...

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The Ask Chapters 17-18 Summary

In great detail, Milo recalls a frightening home invasion near the end of his college career. Three thieves, perhaps believing the apartment to be empty, broke in late at night. While two of them searched the rooms for valuables, the third thief—whom Milo would dub Bat Guy because he brandished a large aluminum bat—corralled the residents in the living room.

Bat Guy’s primary function appeared to be to intimidate the residents while the others looted the place. He broke things with his bat and slammed Billy Raskov’s head into a table. Eventually, Bat Guy took out a gun, set his sights on Constance, and seemed on the verge of initiating some kind of sexual assault.

Out of the corner of his eye, Milo...

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The Ask Chapters 19-20 Summary

Milo arrives at The Best Place, a high-end birthing megaplex, for a meeting with Purdy. On the way he notes that they have archery, breast-milk banks, a spa, and a host of other services to pamper wealthy expectant mothers and their families.

While Purdy and Melinda finish interviewing midwives, Michael Florida keeps Milo company at the bar. Michael and Milo didn’t really socialize directly in college but did hang out in the same group together.

When Milo brings up the home invasion, Michael reveals that he was in on it and knew the thieves. Michael since gave up drugs and alcohol but remains a sex addict. Milo laments being at the other end of the spectrum with a virtually nonexistent sex life.


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The Ask Chapters 21-22 Summary

The exchange in the park was brief, but Milo knows that Paul and Maura are having an affair by their guilty surprise.

That night at dinner, no one speaks except for random utterances by Bernie, who takes out his penis at the table and begins to play with it. Milo excuses himself to get some air but knows he cannot come back to the house that night.

He ends up in his familiar doughnut shop and buys the Kiddie Diddler a sandwich. Milo later learns that Kiddie Diddler used to own the shop and that his brother has done nothing to help him.

As Milo roams the street, he considers the variety of people he could call to find a place to crash (Purdy, even Don) but finally settles on Horace. Horace greets...

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The Ask Chapters 23-24 Summary

Milo calls Don and arranges for a meeting at his house. Christine appears to have deserted her daycare house for the day, so Bernie must accompany Milo to his meeting with Don.

As Don prepares a lunch of store-bought turkey wraps, Bernie quizzes Don about his missing legs. Finally, Milo calls Don in for lunch and the two eat awkwardly before getting down to business.

Milo gives him the figure Lee quoted to pay off Don, and Don immediately asks how much Milo will get for sealing the deal. Milo tells Don he knows that he is a heroin addict; he recognizes the telltale signs in part because he used to do drugs himself.

Don has broken up with underaged Sasha and generally seems depressed. He admits...

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The Ask Chapters 25-26 Summary

At work, Milo discovers a department meeting and decides to attend it, even though he wasn’t invited. Dean Cooley gives a long-winded military-parable-laden speech that eventually ends in congratulating Llewellyn for another big give.

Cooley also mentions that the father of McKenzie, the pampered art student who got Milo fired, is gravely ill. This turns the focus to Milo and, as Cooley tells the room that Milo was not invited to the meeting, Milo prepares for complete annihilation.

Suddenly Cooley announces that Purdy has just made a huge give in the form of an arts center and congratulates Milo on his work.

Later, Vargina reveals that the foreign exchange student sleeping on Cooley’s couch...

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The Ask Chapters 27-28 Summary

Milo wakes up the next morning in the throes of an excruciating hangover. As he tries to nurse himself back to health, he tries to call Purdy, Don, and several others but cannot get through to anyone.

Worried about Don, he heads over to his place and encounters Nabeel, the son of the building’s landlord. After bribing Nabeel with one hundred fifty dollars, he lets Milo into the building and up to Don’s apartment. When Don doesn’t immediately respond to his knocks, he asks Nabeel to let him in, fearing Don may have overdosed.

Suddenly, Don opens the door and lets Milo in. Milo apologizes for the previous evening and Don says he’s about to move back to his hometown; he is fed up with the city and his...

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The Ask Chapters 29-30 Summary

Milo arrives at his mother’s house; his reverie of childhood remembrances is broken when he discovers Purdy and Michael Florida have dropped by for a visit. While the two obviously have charmed Claudia and Francine, Milo is less than happy to see them.

Purdy and Milo head out back to talk as they play tetherball on an old set-up Milo’s father installed years ago. Milo confronts Purdy about all of his lies and deceit, and Purdy confesses he was influential in getting Milo fired because he didn’t want any loose ends.

It is clear that Purdy is trying to feel out Milo to make sure he won’t cause any trouble. He responds to Milo’s accusations by calling him a loser and insulting Milo’s father.


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