With The Ask, Sam Lipsyte follows up his cult classic Home Land with a dark and darkly entertaining commentary on the texture of modern America. A slightly meandering plot structure is tied together with scathing riffs on topics ranging from mediocre education, the waning of capitalism, parenting, office and academic politics, reality television, and frustrated would-be artists. Nothing is spared from the barely controlled yet ultra-articulate narrator’s seething discontent.
Would-have-been-but-never-was painter Milo Burke has secretly harbored his own fantasy world since college—a world in which he is “painting’s new savior.” Unwilling to do the work or take the risks inherent in any artistic endeavor, however, he has been slowly calcifying in Middle America. Milo marinates in his own disappointments and resentments, caused by accumulated and increasing discrepancies between his dream world (artistic glory, burgundy bras, nubile assistants, NPR interviews, and unlimited wealth), and his realities. He has just lost his job in the development office of third-tier “Mediocre” university, a fundraising job at which he never managed to land any big “asks” anyway. His marriage is stagnant at best, his painting non-existent, his son more interested in the intricacies of preschool interactions than in his father’s feelings, and his unresolved feelings toward his own cheating, absentee father (now dead) bleed into most of his interactions. Into this morass of frustration and aimlessness steps Milo’s old college friend Purdy Anderson, who’s wealthy, privileged, and talented at everything but parenthood. Promising a potential big “give” that could reinstate Milo’s job in return for helping him with some personal matters involving a newly discovered adult son, Purdy draws Milo back into his magnetic orbit of privilege and pretense.
There is no denying the sharp and deprecating wit with which Milo skewers both the external world and his own internal failings and inadequacies in an often poetic and alliterative style. Modern America (and what it is or isn’t) is a frequent target, as he deals with privileged Purdy, has fateful encounters with favored-but-untalented offspring of the rich, discovers the impact of reality television on the hopes and dreams of the working class, and navigates the vagaries of office warfare. Never before have turkey wraps taken on such significance in or out of the office. Unable to operate in a world where he has the “old brain,” where jobs “weren’t about experience anymore, just wiring,” he loses out to “kids who lived on hummus and a misapprehension of history, the bright newbies bosses exploit without compunction… each stint on their resumes another line in the long poem of their riskless youth.” America is waning, its promise disintegrated into the ancient and ever-present division between the rulers and the ruled. Of course he says it with much more lacerating wit.
As the disconnected and discontent observer, Milo also takes on relationships—friends, and how friendships past or present are never what one supposed—as well as lovers, and their questionable motives and honesty. Rather than softening pain and disillusion, time seems to have sharpened them into the chisels with which Milo carves his own headstone. Disconnected from his wife as well as his friends and coworkers, he is “warm with that feeling of wanting a feeling that maybe had already fled,” which is a fairly accurate description of his attitude in general. Unable to takes risks, Milo always seems to be a step behind, just missing out, constantly trapped in his own analysis. He becomes unlikable in his self-defeat, yet identifiable in his discomfort in his own skin, his inability or perhaps rather his refusal to keep up, join in. Unable to connect even online, he “is one of those people who hadn’t caught up with the latest social networking site…. still stuck in the last virtual community, a sad place to be, like Europe, say, during the Black Death.”
Only with his son (a “beautiful boy” who has “become an expensive hobby”) does Milo seem to periodically connect. It’s a problematic relationship—“funny, isn’t it, how much you can detest the very being you’d die for in an instant?” But then, as he muses, “I guess that’s just families. Or human nature. Or capitalism, or something.” All relationships are problematic, and Milo’s saving grace is perhaps the love he clearly albeit clumsily and intermittently feels for his son. For Bernie, he is willing to tread the dangerous paths of postmodern childcare at the Happy Salamander (Blue Newt Faction). When not closed for “pedagogical conflicts,” the facility emails manifestos to unsuspecting parents, gives children structured “activity nodes” in which to play at real life jobs, or teaches them about the pain of Native American rituals. It’s as though the social theorizing Milo and other pseudo-intellectuals engaged in during college is now being visited upon his child. As with most other things, Milo submits with resentful resignation: “Child care was like everything else. You got what you paid for, and your child paid for what you could not pay for.” Lipsyte’s take on childcare, both of the babysitting and the daycare variety, or at least Milo’s experience of it, is easily some of the sharpest, most unnerving, and most hilarious commentary in The Ask. Perhaps not having children makes it especially amusing. Readers with children might soon find themselves homeschooling their progeny.
It is in the parental relationship that the novel is grounded, especially the hidden, land-mined ground that lies between fathers and sons: Milo and his deceased yet ever-present father; Milo and his son Bernie; Purdy and his newly discovered son; Purdy and his unborn child; even co-worker Horace and his parents’ implied presence. Which is not to say that women are ignored: Milo’s mother and her lover appear briefly as pivotal figures that are ultimately more sympathetic than otherwise, as do Purdy’s and Milo’s wives. But the father/son connections drive the anger and tension of the action and emotion, present and past (which is always present). While the clear comparisons and contrasts between Purdy and Milo as fathers may seem a bit contrived, they clearly illustrate that the father/son relationship, or lack thereof, is pivotal to Milo’s current state of disconnection and loss.
The other pivotal topic is the arts—Milo’s own pretensions, those of the newer generations, institutional development for them at his Mediocre job, and the arts world in general. In college he paints, sees himself as an Artist, and dreams of being discovered. Resentful of not being born into privilege like Purdy, Milo is ultimately unwilling to back up his artistic dreams with any amount of work or risk-taking (other than stealing paint from his job at Mediocre University). Before graduation, his college mentor and lover Lena tells him her take on his talents and what is required to work in the art world:
“It all comes down to how much you need to inflict yourself on the world…sure there are stars, most of them hacks, who make silly amounts of money, but for the rest of us, it’s just endurance, perdurance. Do you have the guts to perdure?…. It’s not very glamorous. Is this what you want? You’re good enough for it. You’re not the new sensation, but you’re good enough to get by. But you have to be strong. And petty.”
But Milo freezes into inaction, preferring his fantasies and resentments, dreaming of stardom but unwilling to take jobs that don’t meet his idea of the glamorous art world, to work his way in and up. Ironically, he ends up a failure in the world for which he forsakes his art, scraping to get by in middle-class America, trying to survive just as he would have been as an artist.
Certainly the style of The Ask is crisply defined, the riffs stabbing and insightful, and the skillfully twisted humor undeniable. But like much great Renaissance painting, be warned that it’s not to everyone’s taste. Upon first reading, it is difficult to be drawn in by a protagonist who, unwilling to act upon his dreams and talents, resents the rest of the world for his own inaction. The question is does Milo really want to be an artist, or just a superstar with the glory and acclaim? The same question applies to his roles as father, husband, friend, son, employee. The publisher’s publicity blurbs suggest that Milo just wants to be an okay guy but is now finding that even just okay has to be strived for. Lipsyte himself views Milo as simply misdirected: “He’s got problems, but he’s definitely putting in the effort. It’s just not clear where the effort should be directed. He’s in over his head." But unfortunately, Milo comes across more often than not like a child who wants does not want just okay, he wants glory without work. After all, it’s more fun to wallow than to work. If someone doesn’t invest energy in his job, his wife, his family, his passions, why should he be surprised that he’s fired, his wife is distant and unfaithful, he has no family loyal to him, and his art is unexpressed?
I’d be willing to gamble that my irritation is precisely the point, that Lipsyte doesn’t particularly want us to like Milo, the overly sensitive antisocial antihero, although we may sympathize with his awkwardness. Lipsyte himself is somewhat of an anti-Milo, having worked for years at his art with no recognition and frequent rejection until his relatively recent acclaim. Is Milo the author’s alter ego in some way, the parts of himself he’d like to give in to, or is he a scathing indictment of all that author resents in others who, unlike himself, want it all without working for it? Or both? That would explain Milo’s both unlikable yet somehow sympathetic (and dare I say, recognizable by the reader?) nature. It’s easy to both dislike and yet understand Milo; after all, who among us doesn’t find ourselves frustrated by others who embody the things in ourselves we’d rather not see? And isn’t the average American psyche (both individual and collective) largely defined at the moment by feeling we’ve failed at something, by wondering about our choices, yet still wanting something for nothing?
To be fair, Milo does begin to grow up by the end of the book. He even takes some rather drastic and symbolically important action involving a tether ball. Lipsyte grants Milo a few rare moments of clarity:
“A whole treasure trove of cockamamie theories deserved another look. Perhaps, for example, Lena had told me I was only moderately talented because she felt compelled to speak the truth. Maybe Maura still desired me but for her own sanity could stay in our marriage only if I chose to confront my rage and resentment. There was even a chance happiness had something to do with acceptance, and something to do with love.”
But these briefs moments do little to vary the tone. The larger problem is that too much of the book drags. The Ask is supposed to be funny and very frequently is, but it can also become dreary in Milo’s unrelenting self-pity, inaction, and resentments. One or two notes do not make a melody. If more foils and stronger alternatives to Milo’s vision were present, the humor would be more effective and the texture of his characters better revealed. While skillfully written, there’s a detached, ivory-tower academic feel to the way in which life, the universe, and everything is so glibly and authoritatively depicted as hopeless. Underneath the not-so-ironic social commentary, some might find the way in which Milo’s world is presented as inevitable to be exhausting. It is fiction as fashion, where it is chic to be bleak. It will appeal to certain audiences and some of the nuances are better appreciated upon a second reading of the book, but not everyone will find the full blown dark hilarity promised by much of its press.
For most of the novel, Milo appears to almost relish his victimhood, enjoying if not downright wallowing luxuriously in his own hopelessness and depression. Sympathetic and sharply funny early on, The Ask becomes difficult, even painful, in its raw bitterness and its narrator’s helpless self-loathing. As Milo himself says, “If I were the protagonist of a book or movie, it would be hard to like me, to identify with me, right?” to which his former (and perhaps reinstated) boss replies, “I would never read a book like that, Milo. I can’t think of anyone who would. There’s no reason for it.”