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.

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