Songs of the Hurdy Gurley Man

George Gurley sits down in a diner on 9th Avenue to eat a late lunch. By the time his burger arrives, the sun has long ago set, and somewhere across town his girlfriend Hilly is just getting off from work. Gurley thinks there might be trouble ahead.

On a recent Friday evening, George Gurley sits down in a diner on 9th Avenue to eat a late lunch. By the time his burger arrives, the sun has long ago set, and somewhere across town his girlfriend Hilly is just getting off from work. Gurley thinks there might be trouble ahead.

“I work at night, and she gets up really early,” says Gurley, who frequently writes about the city’s nightlife for the New York Observer.

“I haven’t done anything today,” adds Gurley. “She’s been up since seven. This is what’s going to happen tonight. Not a fight. But a conflict.”

Such are the pitfalls of being ready for lunch when your girlfriend is ready for dinner, and of pondering a late night bender when she’s probably pondering a sleepy night at home. For many New York couples it’s a familiar dynamic: the push and pull of individuality versus coupledom, exacerbated by the proximity to so much potential debauchery. But for Gurley — whose job description on any given night can range from slurping down imported Vodka with randy Russian party girls to conversing about sex with seductive socialites — the problem is a smidgen worse.

As a result, several months ago, after roughly three-and-a-half years of dating, Gurley, who is 37, and Hilly, who is 31, entered couples therapy. From the first day of therapy, when they arrived at Dr. Harold W. Selman’ s office on the Upper East Side, Gurley brought along with him more than just his own personal psychological baggage. He brought along a tape recorder.

For the past four months, the typically verboten dialogue of Man, Woman and Therapist has appeared in an ongoing series in the Observer dubbed alternately “Should I Get Married?” “But Should We Get Married?” or “George and Hilly.” The series consists of transcripts of the therapy sessions, lightly edited and presented without interruption.

The result is an addictive and at times maddening portrait of intimacy that lopes along between moments of humor and levity, gravitas and depression.

From the start, observers of the Observer have greeted the series with a mix of curiosity, bemusement, and horror. Gawker published an item announcing the series’ debut with a picture of Gurley and a concise observation: “Overshare!” Choire Sicha, a senior editor at the Observer and Gurley’s officemate, posted an item on the paper’s Web site comparing the series to a car wreck. Elsewhere, the New York Times’ gossip columnist Campbell Robertson noted that, “The account has an eerie, anthropology-experiment feel, with noneventful passages alternating with passages that broach Mr. Gurley’s sometimes bizarre behavior.”

To wit: Gurley has told Dr. Selman about losing his virginity at age 7 or 8, admitted to yelling at his cat, and confessed to berating Hilly for not reading the New York Times every day. For her part, Hilly has told Dr. Selman how she recently “swatted” a girl in a nightclub who was talking to Gurley, confessed to strong-arming Gurley into buying her a pre-engagement ring, and admitted to having a drink before therapy because she was anxious about talking about sex. Even Dr. Selman has gotten in on the confessional candor, telling Gurley and Hilly at one point that he, the couples therapist, is separated from his wife.

“At first it was really weird when this stuff came out,” says Gurley. “I’d be out reporting, and I’d run into someone who had seen the column. I first get this kind of stricken look. But it’s almost like it’s not me. I’m detached from it. Every other story I’ve done for the Observer for ten years, Wednesday morning when it comes out, I read it on the Internet. Then I get a copy, and I kind of study it. This one, I don’t do that. I don’t want to see it.”

Hilly, on the other hand, says that every Wednesday when the series comes out, she cuts out the column and glues it into a scrapbook. “It’s something I never want to forget,” says Hilly.

She says that so far most of the feedback has been positive. “My family is pretty addicted to it,” says Hilly. “They think of it as a soap opera.”

Occasionally, she says, they give her a hard time about her big city, hard-drinking lifestyle. “They’ve started calling me Joan Kennedy,” she says.

Gurley says that his parents also enjoy the series. His mom, a former therapist, now lives in New York. His dad is an accomplished print journalist and playwright who lives in Baldwin City, Kansas. They divorced when Gurley was a young child. Several decades later, he has managed to unify both of his parents’ intellectual pursuits — therapy and journalism.

For years, George Gurley the Elder wrote a popular column in the Kansas City Star. In 1991, he wrote a column titled, “Get a life, get a job, get going,” focusing on his son’s lack of professional direction after graduating from college. (In the article, Gurley the Younger explained his ambitions thusly: “I want to make enough money so that I can afford a new pair of socks every day.”)

Gurley Sr. — whose recent column subjects for the Lawrence Journal-World include meditations on the “Proustian” effects of raking leaves and observations on a cross-country road trip from Alaska — says he supports his son’s choice of column material, even though it makes for some challenging reading.

“It’s an unusual situation,” says Gurley Sr. “I think the thing about something like this is that you find out some things about your son that you wouldn’t necessarily know otherwise. If I were to call him up and say, I want to have a man-to-man talk about this stuff, it would probably be a short conversation. … This thing is brutally honest.”

Whereas Gurley the Elder has gotten over his initial reservations and come to fully embrace the series, the opposite has happened with one of his son’s colleagues. Last year, Gurley penned a persuasive profile of Dorothy Rabinowitz, the Pulitzer-prize winning columnist for the Wall Street Journal, which the Observer published under the headline, “Ravishing Rabinowitz of the Right.” After initially liking the “George and Hilly” series, Rabinowitz says she eventually turned against it.

“When I first heard about it, I said, ‘George this is gold. Gold!” says Rabinowitz. “I thought this is like a portrait of a marriage, scenes from a marriage, and you know, you get all this data and maybe you would make a film of this. Little did I know as it immediately progressed, this is turning into the most … what should I call it? … narcissism on steroids.”

“Put exhibitionism aside,” adds Rabinowitz. “Put everything else aside. They go to this doctor to see if they can get their relationship together to go forward. Everybody who has had any life experience knows you cannot make a relationship work by working on it. You can work on a kind of showbiz enterprise and the fun of it all, and that might have brought them together. But as these pieces got more and more serious, I began to see that this is really depressing stuff. … What I don’t understand is, how somebody who has grown up in the ’70s and ’80s and ’90s culture of sophistication and permissiveness could be walking around with this Victorian burden of I have to do right by this woman.”

Despite her doubts about the column and the value of couples therapy, Rabinowitz keeps reading the series, which she is capable of citing, chapter and verse. “I keep reading it because I keep thinking it’s going to even up a little bit,” she adds. “But as it turns out, George is always on the defensive. … What will happen ten years from now, when one looks back on this? You know, youthful follies. But it is a folly. To me, it’s a supreme type of folly.”

“I think both of these people are very smart,” says Rabinowitz. “There’s an animal smartness to both of them. And both of them understood that this is going to make a splash. For journalists, a splash is good. That’s perfectly respectable stuff. However, it’s completely uncontrolled now, as all these things are. Even when you’re posturing, there’s a certain profound element of reality that emerges. All the little things are just not said in jest. She is not up to his standards. Period. If he’s feeling that way now, what is he going to feel ten years from now?”

In the meantime, “George and Hilly” continues to stand out in what might be thought of as the Golden Age of Sex Columns. Recently, New York magazine convened a symposium of sorts in which six female sex columnists discussed the state of the art. At one point during the “Vagina Dialogues,” the columnists noted how few of their colleagues are men.

“What I think is really interesting at this table is, where are the guys writing about sex, beyond [gay syndicated columnist] Dan Savage?” said Rachel Kramer Bussel, the Lusty Lady columnist for the Village Voice. “I think it stems from straight guys not being as comfortable talking about sex in general.”

Bussel thinks that the “George and Hilly” series is unique not only because Gurley is a straight male writing frankly about sex but because of the unfiltered quality of columns. “I totally admire him for putting that out there,” writes Bussel by email. “I certainly don’t think I could do the same — reading it, it struck me that the things one might say in therapy are different from things even the most confessional writer would bring up, or think to bring up.”

“I think the difference with their back and forth is not that we haven’t read really personal memoir-type stuff, but after the fact, where someone has time to gather their thoughts and sort of portray themselves how they want to be seen,” she adds. “Whereas with the therapy it seems like there’s less self-censoring, less self-consciousness and just this very direct, honest view, like slicing open someone’s brain without warning.”

During one therapy session, Hilly tells Dr. Selman that she got mad at Gurley when his picture appeared on, standing next to a socialite, who Hilly describes as “probably the most gorgeous woman in the whole city.” David Patrick Columbia, who runs the site, says he feels bad for Hilly. “It’s exploitation,” says Columbia. “I think George is exploiting their relationship for his work. Journalists get all the attention now by wagging their dongs out in public air. It’s very self-absorbed and self-obsessed, which makes being in a relationship with someone else impossible.”

Gurley is quick to point out that the idea to write about the therapy came after his and Hilly’s decision to see a therapist. One day Gurley mentioned the therapy sessions in passing to the Observer’s Executive Editor Peter M. Stevenson. It was Stevenson who first suggested that Gurley write about it.

At first, Gurley thought Stevenson was joking. A decade ago, when Gurley started as an intern at the Observer his nickname around the office was Clown Boy. Pranks had been played on Gurley in the past. But that was years ago, when he was fresh out of Kansas, before he emerged as one of the paper’s best writers. This was no prank. Stevenson kept pushing the suggestion.

A few weeks later, Hilly and Gurley met with Stevenson and Peter W. Kaplan, editor of the Observer, to discuss the idea. “About ten minutes into it,” Gurley recalls, “Peter Kaplan said, ‘Say no more.’ He wanted to start tape recording right there. He said, ‘We don’t even need a therapist. We’ll just put the two of you in the room with a tape recorder.’”

Stevenson has something of a track record with this sort of thing. This isn’t the first time that he has helped shepherd a series about sex and relationships into the pages of the Observer. The last time Stevenson edited a similarly aberrant column it was a little thing called “Sex and the City.”

In the mid-’90s, long before “Sex and the City” spawned the HBO series and begat an entire worldview, Candace Bushnell wrote stories for the Observer in which she nimbly stripped away the outer layers of her friends and associates to uncover various archetypes of New York City, from Modelizers, to Toxic Bachelors, to Mr. Big. For years, Gurley has been using the same peach-colored pages to do just the opposite: he takes archetypes of New York City and adds layer after layer of intimate detail until his characters have names, histories, quirks, and life stories. Sociopath stockbrokers. Dysfunctional socialites. Functional alcoholics. Fallen aristocrats. Rising social climbers. Exhitionist artists. Held in Gurley’s gaze for long enough, these familiar types become more and more strange, complex, and human.

The “George and Hilly” series reads like the typical Gurley approach, only applied to himself. In the process, he grinds up his own archetype — call him Mr. Pre Engagement Ring — and gives us the sometimes bloody and always unpredictable details of individuality. Whereas Bushnell mastered the art of taking a small amount of data and turning it into sweeping, irresistible trends, Gurley has taken a trend and turned it back into raw data. Literally, the transcripts.

Jim Windolf, a contributing editor at Vanity Fair, and former editor at the Observer (and who edited Gurley’s first contribution to Vanity Fair) describes “George and Hilly” as a “mad journalistic experiment.” And one that is perfectly in stride with Gurley’s broader oeuvre.

“George is always chronicling New York — the things people will do as they go after pleasure and success,” writes Windolf by email. “This series fits right in with that. He’s also great at getting small details into print that could otherwise be lost. I’m talking about things like the ‘Muppet face’ and the bathtub pillow and how George deals with his cat.”

“Almost all his pieces are comedic, too, which is rare in journalism,” adds Windolf. “I’m always thankful to come upon a funny article. Gurley also tends to present material to readers and to let them make up their own minds. For instance, a lot of people go into couples therapy. Is it worthwhile? The series doesn’t really take a stand, but it probably gives a lot of ammunition to anyone who suspects it’s a waste of time.”

“George uses his tape recorder to let people talk and talk until they reveal themselves,” adds Windolf. “Sometimes the subjects of his stories are embarrassed afterward. He lulls them into saying things in a public forum that they might not even say to their friends. This time he’s doing it to himself (as well as Hilly and the therapist).”

Is there anything Windolf doesn’t like about the series? “It gives me the creeps,” writes Windolf. “And there’s no end in sight.”

To date, the Observer has published 10 installments of “George and Hilly,” to the tune of roughly 25,000 words. Is there really no end in sight?

According to Gurley, the series will go on until his editors pull the plug. Due to the expense of the therapy sessions, Gurley says he might cut back on the frequency of the columns, which appear somewhat irregularly every few weeks. Gurley says that each hour-long session costs $200, and the paper does not pick up the bill.

Gurley says he has also dabbled with the idea of adding “guest appearances” to the therapy sessions. “My grandmother, she’s 92,” says Gurley. “She came back here in October. I wanted to bring her in. She’s read a few of the columns. But there were a few columns that weren’t appropriate. I think it might be too gimmicky.”

At least for the time being, the world of New York City sex columns will remain free of grandmas. But perhaps not from cab drivers. During a recent drunken ride across town with Hilly, Gurley solicited some relationship advice from a cab driver named Sydney, who compared marriage to a business and quoted Gurley a passage from the Bible. Gurley loved it. Perhaps sometime in the future, “George and Hilly” might hit the road.

In the meantime, Gurley will keep churning out his signature moments of candor. “I’ve just got to confess something,” Gurley told this reporter, while polishing off his evening lunch:

“It’s not a lot of work. I just put down the tape recorder. I’m getting a little vacation, here.”

Correction: The above article has been changed to note that Jim Windolf edited only Gurley’s first contribution to Vanity Fair.

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Felix Gillette writes about the media for The New York Observer.