Cover image of "The Ask," a novel by Sam Lipsyte about a career in fundraising

Meet Milo Burke, as inept, unstable, and self-doubting as any anti-hero who’s ever walked the earth. A failed painter whose sophomoric delusions of grandeur have long since drowned in waves of self-pity, Milo is employed in fundraising at what he insists on calling Mediocre University in New York City. His job is to snag egotistical, self-interested rich prospects and sweet-talk them out of large sums of money to fund arts projects of highly dubious value. Milo is totally inadequate to meet this challenge, as he is at everything else in his life, and in the space of one short novel he is fired twice. So much for his career in fundraising.

Milo’s life off-campus is at least equally tragicomic: his 71-year-old mother has come out as a lesbian and appears to be sharing a tent in the living room of the family home with a loopy partner; his unresponsive wife is sleeping with a gay co-worker at her marketing job; their 3-year-old son is more attached to his mother’s lover than to his father; and for reasons never explained other than to hint that it possesses vast symbolic value, Milo is obsessed with a Spanish dueling knife his philandering, drug-addicted father gave him shortly before his death.

The Ask by Sam Lipsyte ★★★☆☆

If this isn’t a set-up for black comedy of the classic variety, what is? In fact, Lipsyte’s rich, often elliptical style brings laugh-out-loud humor to the story from time to time. Other readers have found the book hilarious from cover to cover, but I didn’t. Who knows? Maybe Milo’s inner dialogue hits a little close to home. My own career in fundraising had its disappointments, too.

Although The Ask is ostensibly the story of a fundraiser — a university development officer — it is by no means an instruction manual for those who labor to raise money for worthy institutions. I’d picked up the book because I have spent three decades as a fundraiser. After all, there aren’t that many novels written about us and our work. But The Ask doesn’t come close to doing that. Milo and his colleagues break just about every rule in the fundraiser’s book. And maybe, after all, that’s why I found much of the novel unfunny.

Like Milo Burke, Sam Lipsyte was born in New Jersey and lives now in New York City. The Ask is his third novel.

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