Where new writing finds its voice

The Ask

Gavin James Bower

Interview with Sam Lipsyte

Sam Lipsyte is a funny guy.

I know this, not because of the blurb on the jacket of his latest novel, The Ask, which follows a failed-painter-turned-failed-arts-college-fundraiser as he attempts to extract money from an old school friend, who also happens to be a multi-millionaire.

It’s also not because of the interviews with Lipsyte I read before writing this, including the one in which he describes the art of ‘fish fighting’: essentially, fishermen engaged in brutal rod-to-rod combat, with hilarious consequences for all concerned – apart from the fish, of course.

No, I know this because of the two email conversations I’ve had with Sam, and the fact I’ve read The Ask.

He’s not short of supporters for his particular brand of rip-roaring literary humour either. Fight Club author Chuck Palahniuk wrote of Sam’s prose, ‘I laughed out loud. And I never laugh out loud’. While Geoff Dyer noted in a recent Observer review, ‘The Ask is hysterically funny, even excluding the passages where you’re too busy mentally applauding and calculating the many ways in which it’s funny to laugh.’ Even Vanity Fair reckons Sam is ‘so funny you might lose an eye’ – whatever that means.

Lipsyte has previously penned two other novels and a book of short stories, but it’s The Ask that has finally got his home nation in a fluster. The book is already a New York Times bestseller and a monster hit with critics in the US.

So what is it all about? The Ask centre around Milo Burke, husband to a ‘touched out’ wife, father to the precocious three-year-old Bernie, and a man who’s found himself on the wrong side of the American Dream. 

The prose is rich and thick and before you’ve even had time to adjust your reading glasses, you’re thrown head first into the lewd, crude spectacle of Milo at work: 


America, said Horace, the office temp, was a run-down and demented pimp. Our republic’s whoremaster days were through. Whither that frost-nerved, diamond-fanged hustler who’d stormed Normandy, dick-smacked the Soviets, turned out such firm emerging market flesh? Now our nation slumped in the corner of the pool hall, some gummy coot with a pint of Mad Dog and soggy yellow eyes, just another mark for juvenile wolves.

‘We’re the bitches of the First World,’ said Horace, his own eyes braziers of delight.

We all loved Horace, his clownish pronouncements. He was a white kid from Armonk who had learned to speak and feel from a half-dozen VHS tapes in his father’s garage. 

Besides, here at our desks with our turkey wraps, I did not disagree.


But fundraising isn’t quite Milo’s forte, and he soon loses his job for verbally abusing one of the college’s many silver-spoon-up-the-arse students. 

Things aren’t looking much better at home. When Milo finally cajoles his wife, Moira, into bed, only to pass out, he wakes up in the middle of the night to find Bernie breastfeeding from a dry nipple. When he suggests that the interloper should, well, leave them to it, he’s told tersely to go back to sleep. By Bernie.

The voice of Milo had me hooked right from the word go. You can’t help but like him as much for the fact he’d doubtless buy Catch-22’s Yossarian a beer, as for the narrative’s Seize the Day sensibility.

I start by asking Sam about that Palahniuk quote. ‘Chuck wrote that blurb ten years ago for my novel The Subject Steve, and it was a big thrill to get that,’ he explains modestly. ‘Praise from people you admire and respect is a good feeling, obviously. You go through so many phases of loathing yourself and your work (or at least I do) that encouraging words from the outside can really sustain you in the dark hours.’

Despite the obvious differences – Milo doesn’t suffer from schizophrenia, nor does he have a penchant for underground boxing – a comparison with Palahniuk’s generation-defining novel is not that far-fetched. Slap bang in the middle of a global recession Milo’s is a voice the world-weary white-collar workforce can really get:


The privileged of our generation did what they could, like the rest of us. We were stuck between meanings. Or we were the last dribbles of something. It was hard to figure. The fall of the Soviet Union, this was, the death of analog. The beginning of aggressively marketed nachos.


Indeed, The Ask speaks to a lost generation of office workers too tired even for cynicism and, given the state of the global economy, is culturally pertinent in a way most writers would kill for. Talk about being timely, if you’ve got something to say about the world post-crash, now’s your chance. But Lipsyte sees the subject matter as more organic.

‘Well, it’s never really worked for me to sit down with something to say,’ he explains. ‘I just want some sentences to come alive. My sense about these things is that if you sit down to write a savage critique of your municipal transportation system, the burden could undo you. But if you are somebody for whom the savage critique of your municipal transportation system is truly part of your internal chorus, it will bubble up into the work all by itself. Then when you see it there, you can begin to consciously frame it, shape it.’

Comparisons with blockbuster novelists aside then, you’d still be forgiven for thinking life as a writer has been straightforward for Sam. In reality, though, it’s been anything but. His first novel was inauspiciously published on 11th September 2001, and it didn’t shift, while his second, Home Land, was roundly rejected by US publishers before being picked up in the UK.

It’s only now, with The Ask, that things are starting to go Sam’s way: ‘Imagine one of those pre-Wright Brothers flying machines, the kind that has a man strapped into the middle of a wooden frame,’ he says, when pushed to describe what I call his career trajectory. ‘You’ve seen the footage. The contraption gathers up speed, lifts a few feet off the ground and then flips violently, or tumbles over a cliff. But the pilot doesn’t know he’s going to be a comical also-ran on some jittery film loop. He thinks he’s about to fucking fly.’

‘Or maybe this isn’t my career trajectory,’ he continues, ‘just an average day…’ Which brings me back to the ‘funny’ thing. The term ‘comic writer’ almost seems pejorative. It shouldn’t, but it implies that to write with humour is distinct from just writing – and, for that matter, writing well.

‘I know what you mean about the way people talk about the category,’ he says. ‘I guess at this point I don’t think it’s a very useful term. I thought it might be, but some people still can’t seem to accept the notion that something can be funny and meaningful at the same time, at least in fiction. I just don’t care for fiction that takes pages of heavy breathing to get to the same place that others can reach in a few poetic, striking, and, yes, often hilarious sentences.’

Hilarious sentences, as well as some brilliantly funny set pieces, are elements The Ask is not exactly short on. Like the one that involves Milo, a colleague of his, the delectable Vargina, and her immaculately crafted egg salad. This scene, and
I’ll avoid a spoiler, ends with what Palahniuk might’ve been getting at in his blurb: a laugh-out-loud climax.

‘I don’t really write toward a punchline,’ Sam counters, ‘but just try to follow whatever weird elements I’ve put into play. I’m never sure where it will lead me. Sometimes it all falls together and sometimes it all falls apart.’

Speaking of falling apart, The Ask’s narrator is a very amiable loser. I found it hard to dislike Milo Burke – anyone who says things like ‘dick-smacked’ and ‘spidercunt’ in everyday conversation is all right with me – but I had a feeling, when I was reading the book, that maybe I should.

One conversation sums this up perfectly –
when Milo and Vargina are together in the proverbial darkened room, and she tells him just what she thinks:


‘No, I mean, if I were the protagonist of a book or a movie, it would be hard to like me, to identify with me, right?’

‘I would never read a book like that, Milo. I can’t think of anyone who would. There’s no reason for it.’


But while Vargina’s feelings are patently obvious, does Sam like Milo Burke?

‘I can answer this question,’ he says, ‘but only with your confirmation that you are aware he does not exist…’ I confirm. ‘I love and hate every character in the book. They’re all me and they do not exist!’

Another loaded exchange that captures Milo’s problem involves Lee Moss, a wonderful literary creation – full of aphorisms and left-of-centre pearls of wisdom you’re going to want to try and pass off as your own at dinner parties. Milo, having been re-employed at the request of Purdy Stuart, the old school friend he must now service to keep his job, soon realises he’s in above his head. The ‘ask’, no longer merely about squeezing money out of the rich to fund what appears to be a bloated and pointless educational establishment, is getting complicated. And, with Milo clearly floundering, Moss offers this astute advice: ‘We are going to eat ice cream and we are going to eat shit. The trick is to use different spoons.’

‘I like that line as well,’ Sam admits. ‘I guess it’s Milo’s problem; everybody’s problem. But I don’t necessarily see Moss’s aphorism as the wisdom Milo must adopt. One can also forego both ice cream and shit…’

But isn’t life much better when you’ve tasted the bitter, I reason, so you can really enjoy the sweet? Or is that just a load of shit?

‘I don’t know, is it better? Do the flavours of fine pastry really only come out after you’ve been beaten with sticks? Of course we can’t avoid bitter moments in our lives, but I think the above-quoted statement suggests we are all going to enter into the bargain where we eat a certain amount of other people’s shit (our employer’s, for example), in exchange for ice cream.

‘But if you decide you don’t need the ice cream,’ he continues, ‘maybe you can reduce the turd intake. Find a middle ground of, say, a nice sandwich.’

It’s this middle ground that Milo can’t quite manage to find, although, by the end of the novel, he at least seems to realise his predicament – a realisation, I’d argue, which gives all of us hope.

While out walking in the park with Bernie, with just a few pages left, Milo tells him to be ‘a good boy’, but backs up this safe advice with more ambiguity, telling him that nothing is sacred:


‘Don’t save a little part of you inside yourself. Not even a scrap. It gets tainted in there. It rots.’

‘What does?’

‘I can’t explain right now. Someday you’ll know. But promise me you’ll squander it.’

‘I promise. What’s squander?’