By Alex Williams
nyt.com

“OH, Jon-Jon!”

Lorin Stein, the editor of The Paris Review, was inspecting an advance copy of Jon-Jon Goulian’s new memoir, “The Man in the Gray Flannel Skirt,” at a party at The Review’s TriBeCa headquarters on a recent Wednesday night.

Next to him stood Mr. Goulian, an old friend, who bounced on the balls of his feet in anticipation, looking like a star (or starlet) in the making, his eyes hidden behind rhinestone-encrusted Gucci sunglasses.

Mr. Stein, like a lot of the men there, seemed to have beamed in from 1962. He wore a skinny regimental-stripe tie and herringbone tweed jacket, and periodically freshened his drink from a bottle of Scotch stashed in a metal file cabinet, a Nat Sherman cigarette dangling from his lips.

Mr. Goulian, by contrast, seemed to have beamed in from a future century. Head shaved and body toned like an Olympic swimmer’s, he wore a brown knee-length tie-dye skirt, five-inch Steve Madden wedge sandals and lip gloss. He drank only tap water, and winced at the cigarette smoke that hung in the air.

Seated on a windowsill in his office, Mr. Stein ran his finger down the gushing blurbs printed on the book’s back flap from the writers Walter Kirn and Gary Shteyngart and paused on one from the novelist Benjamin Kunkel: “If Jon-Jon Goulian did not exist, it would have been necessary to invent him.”

Mr. Stein peered up adoringly at his friend: “I’ve often felt that.”

Mr. Goulian is, by his own account, a hot mess of contradiction. A former baby sitter, law clerk, freelance personal trainer, and assistant at The New York Review of Books (“the only person who ever took the job for the money,” he said), he presents himself, at age 42, as an androgynous man-child with hermit tendencies.

Nevertheless, his Capote-scale party skills have made him a kind of mascot for the city’s literary A-list. And while his own writing output until now consisted of a few assignments for Slate, which he never filed, his first book — a sprawling comic memoir of a life spent battling countless neuroses and defying expectations of everyone close to him — earned him a $750,000 advance.

He is now a client of the powerful Wylie Agency. He was named to Rolling Stone’s list of Hottest Breakout Stars of 2011, as well as Out magazine’s “Hot List” (Mr. Goulian says that he is, except for a bit of adolescent experimentation, straight).

But will American book buyers be as charmed and intrigued by this walking paradox as New York’s writerly in-crowd?

“Are people inherently interested in the subject of Jon-Jon?” asked Sloane Crosley, a socially connected writer who also provided an enthusiastic blurb for the book. “Probably not, but that’s irrelevant. He has this totally unique brand of masculinity mixed with charming vanity.”

In February, Random House took the unusual step of holding a book party to celebrate the release of the review galleys of the book, three months before its actual publication this week. Held at the Wooly, a too-cool lounge in the Woolworth Building, it attracted more than 150 publishing insiders, many of them plucked from the mastheads of Vanity Fair, Harper’s Magazine and Esquire. Many, including Katie Roiphe and Larissa MacFarquhar, one of at least seven New Yorker writers in attendance, counted themselves as close friends of the honoree.

Mr. Goulian certainly cut a curious figure there, his face made up like a David Bowie sideman from the “Hunky Dory” era, as he traded industry gossip with Andrew Wylie, who was dressed like a Threadneedle Street arbitrageur in a gray suit, while Depeche Mode blared over the loudspeakers.

“The New York literary world could use a few more curious figures,” Mr. Wylie said moments later. The agent, who represents Philip Roth and Dave Eggers, was asked who came to mind when thinking about this latest literary sensation. “My mother,” Mr. Wylie said, casting a glance at Mr. Goulian in a sarong-length gray skirt.

It’s easy to see why publishers might consider Mr. Goulian an easy sell. In a culture dominated by reality TV and weepy confessionals, his story makes for ideal back-flap material. (In a review of the book in The New York Times this week, Dwight Garner called it a “loquacious, high-strung, daft and vaguely sad new memoir.”)

A grandson of the political philosopher Sidney Hook, Mr. Goulian grew up in a household humming with high achievement. His father was a doctor, his mother a lawyer; one older brother went to Harvard, the other Yale. Through his first years of high school, Jonathan Goulian, an A-student and soccer standout, seemed on the same path.

Then he veered sharply off it — showing up at his senior prom wearing white tights, high heels and a Viking helmet. Before long, he rechristened himself Jon-Jon. “Jonathan just seemed too masculine for me to live up to,” he recalled. “There was something childlike, delicate, fragile about the nickname Jon-Jon.” What Mr. Goulian was struggling with was not sexual identity issues, he insists, so much as general identity issues. After puberty, he found himself paralyzed by body insecurities, sexual inhibitions, hypochondria and the expectations of upper-middle-class society.

“You hit 12, 13 and suddenly so much is at stake,” he recalled on a recent Friday, over a lunch of unsalted nuts and fresh figs at the rambling Upper West Side apartment where he has been staying with an old family friend, a woman in her 70s. “It’s not just about playing soccer and getting into the right college. It’s not just about wearing the right clothes and being presentable. It’s about being good-looking and to hook up with the right people. And I never really made it past there.”

His escape was to render himself unrecognizable. He started wearing skirts and makeup — though not, as he saw it, in a “gay” way. At 15, he begged his parents to pay for one nose job (he paid for another one himself when he was 24). “Certain things are expected of a boy who’s making his way through life,” he said. “But maybe nothing would be expected of this weirdo.”

As a portrait of a young man doing his best to make a hash of his parents’ best-laid plans, “The Man in the Gray Flannel Skirt” is a story of relentless self-doubt and the endlessly sliding sideways through odd jobs, with the author losing himself in fleeting obsessions, like body building or collecting serial-killer cards.

At times, Mr. Goulian did try to appease his parents, he said. He graduated from Columbia, and New York University law school, and clerked for a federal judge. During his 20s, he worked at a law firm that handled white-collar and organized-crime cases.

It was during those years that Mr. Goulian fell into a group of young writers that included Ms. Roiphe and Ms. MacFarquhar, whom he met through the journalist David Samuels, who was dating one of Mr. Goulian’s roommates at the time. Back then, Ms. Roiphe recalled, Mr. Goulian didn’t seem to have any literary ambitions. (“I still don’t have any literary ambitions,” Mr. Goulian retorted.) “The first ambition I can remember was just the ambition to not be a lawyer,” she said, adding that he covered his neck and arms with so many tattoos that he effectively made it impossible to put on a suit and look professional.

Mr. Samuels recalls Mr. Goulian back then as “ferociously inquisitive and smart, but he really hadn’t read anything.” In pre-Gatsby fashion, Mr. Goulian asked him to compile a list of must-read books. “I made him a list of books: ‘Moby Dick,’ Hemingway short stories, ‘The Devils’ by Dostoyevsky. Then I watched him buy all the books and read every one of them, and read them with this fierce scrutiny and ability to retain whole pages, and recite, word for word. I thought, this is serious.”

When he finally left the law, Mr. Goulian took a stab at screenwriting. He cut a demo record as an electro-pop performer. Nothing took. Eventually, a friend tipped him off to a temporary manual-labor gig, which turned out to be a job organizing the personal library of Robert B. Silvers, the editor of The New York Review of Books. He ended up applying for a job as his assistant. The application involved writing a five-page analysis of a feature by a well-known Review writer.

Mr. Goulian responded with a searing 20-page analysis in squint-inducing eight-point type (never mind that Mr. Silvers at the time was in his 70s).

He got the job anyway, and went on to decorate the offices with stuffed animals from his personal collection.

He provided more than comic relief, however. “He was a brilliant editorial assistant,” Mr. Silvers said. “He was very, very helpful in analyzing and criticizing manuscripts, some of them highly complex. He combined a fine sense of language with the skills of a first-class lawyer.”

He was also succeeding at parties, the one setting where the perpetually skittish Mr. Goulian seems to feel comfortable. His logorrheic, hyperkinetic charm quickly gave him a foothold in an insular world, where poseurs are typically snubbed or mocked, Mr. Samuels said. His transgressive image gave him a certain cachet, too.

“Most writers are geeky and slovenly and could stand to lose 10 pounds,” Mr. Samuels said. “And here’s this super-cool, tattooed, 3-percent-body-fat guy who wants to be your friend and talk about books. So at a literary party, he’s the person everyone wants to talk to.”

IT’S tempting to see Mr. Goulian’s outrageous persona as a pose, a marketing ploy: the Lady Gaga of literature. But friends insist there is nothing canny about it. “He’s always been a kind of crazy free spirit,” Ms. Roiphe said. “When I say crazy, I mean actually crazy.”

After he left The New York Review in 2003, Mr. Goulian had something of a lost decade, cobbling together his rent by cleaning houses, or collecting review copies from editorial friends and selling them at the Strand, he said. Despite his social appetite, Mr. Goulian can spend months in seclusion at his grandfather’s old house in Vermont, or weeks in his New York apartment without seeing anyone, friends said.

And romance? “I’ve never had a sexually sustained relationship that lasted longer than two weeks,” said Mr. Goulian, who writes freely about masturbation in the book.

As the book makes clear, he has been freaked out by the squishy details of physical intimacy since he was a teenager. During adolescence, he had four sexual encounters (two with girls, two with boys), but Mr. Goulian didn’t lose his virginity (with a woman) until college. These days, he doesn’t “date” in the traditional sense, but does occasionally “hook up,” and only with women, he said.

Still, sexuality is a vexing issue for him. At one point in his 30s, Mr. Goulian — who says he had never smoked anything, or had taken any other type of drug aside from the occasional drink — even tried a monthly regimen of Ecstasy to try to delve deeper into his sexual psyche. “I’m turned on by women, and like hooking up with them, especially super-smart or powerful ones, but before long all I wanna do is cuddle with them,” he wrote in an e-mail.

“Ecstasy, I was told, opens you up, gives you a little window into the subconscious,” he continued. “Maybe on E, I thought, I’ll dig guys, and that’ll explain everything, but that’s not what happened. I just babbled my head off to strangers and danced alone in a corner.”

Mr. Goulian said that he hoped that the sustained self-analysis (“the only kind of analysis I can afford”) that came with writing a memoir for two years might help him untangle his psyche. It didn’t.

“It’s not like I’m doing this to build character, to see how much abuse I can take,” he said of his outré attire. “It’s not a book about a rebel. A rebel is someone who aggressively asserts his individuality in the face of the pressure to conform. That’s not the person in this book. This is a person who, out of an inability to conform, is falling back on the shield behind which to hide. It’s out of cowardice, not boldness.”

Of course, wandering around New York City in a get-up almost guaranteed to attract jeers from construction workers seems like a funny way to avoid judgment.

“You’re being judged, you’re being called stuff, yeah,” he agreed. “But,” he added, with a measure of satisfaction, you’re “not being asked to be a doctor anymore.”