Rosie Schaap. (Photo: M. Sharkey)

Rosie Schaap is a born regular.

The Drink columnist for The New York Times Magazine and author of the new memoir Drinking with Men (Riverhead, 288 pp., $26.95), Ms. Schaap has a gift for camaraderie—and excellent taste in booze. She’s also become the book industry’s resident bartender, if publishing holiday parties are to be believed (she mixed drinks at PEN’s bash in 2012), and judging by the often-bookish crowd at South, the Brooklyn dive where Ms. Schaap works day shifts.

Drinking with Men roves from Metro-North bar cars to rural Vermont to Dublin, describing the many pint-glass microcosms Ms. Schaap has found herself a part of thanks to her affection for a neighborhood haunt. It would be hard to call a Times columnist an outsider, but she does bring an uncommonly friendly face to New York’s insular book scene.

“She’s always been a part of this bigger literary community that doesn’t necessarily fit into the neat Park Slope package,” said novelist Jami Attenberg, a friend who first met Ms. Schaap at now-defunct Lower East Side bar Good World, one of the establishments described in the memoir.

And while there’s an easy appeal to pairing booze and prose—and certainly no shortage of real-life case studies—Ms. Schaap’s story mostly dodges hard-living artist clichés.

“For me, drinking and writing have never gone together that well,” Ms. Schaap, who turns 42 this week, said to me, adding that she was only able to get serious about writing when she got less serious about drinking.

And yet: “The intersection of writing and bar culture is so natural,” said novelist Kate Christensen, another friend. “Writing is an extension of talking, and talking happens in a bar.”

So I went to South Slope, where Ms. Schaap lives and works, to see a regular in action and do some talking in bars.

Narrow and snug, far enough afield that it’s not a destination for outsiders or a convenient stop for commuters, South is filled with regulars. Ms. Schaap works the day shift on Tuesdays. It’s mostly a beer and whiskey place, but word has gotten around that Ms. Schaap makes a fine cocktail, and as soon as one person at a bar orders a Manhattan, someone else is bound to decide against PBR. I asked Ms. Schaap to estimate how many of the people in the happy hour crowd she already knew. She paused to count.

“Three-quarters,” she said. That included some staff, but staff members hanging out off-duty are a good sign for a bar. Most of her co-workers are younger, lots are musicians, and a couple are transplanted Dubliners. One of the young Irish barbacks has to leave the country soon, but she’s already scheming to bring him back. She’s trying to talk him into journalism school and a student visa—she wants to make an “old-school” city reporter out of him.

“Just what these young Dubliners need,” she said, “is a pushy Jewish mother.”

Ms. Schaap’s own mother was a would-be actress, and her father was Dick Schaap, the prolific sportswriter and longtime ESPN host. Peter Falk, as in Columbo Peter Falk, introduced the pair. They split up when Rosie was 7, and her dad was often absent. But he served as an example, “a real worker-writer.”

“I grew up with this idea of a writer as someone who sat at a table—at that time, at a typewriter, a massive IBM Selectric II—and wrote all the time,” she said. “There was no real mystery or romance. It’s a job.”

And if her father set the example for writing, her mother set the example for talking.

“To everybody,” Ms. Schaap said. “You know, if we were waiting for a table in a restaurant, my mother would tell the maitre d’ that she’d seen the gynecologist that day.”

She and her mother did not always get along, but one of the book’s surprises is her mother’s impressive gameness in the face of teenage rebellion. Rosie drops out of high school and leaves home to follow the Grateful Dead on tour, and while her mother’s not exactly thrilled, she doesn’t disown her. She makes Rosie agree to get her GED, and checks up on her via her psychoanalyst. Ms. Schaap is at least a fourth-generation New Yorker, she points out, so naturally the psychoanalyst had been around since she was a teenager. Ms. Schaap said she knew she wanted to leave home the first time she saw the Dead.

“I understood that it was a ready-made, traveling community,” she said. By her first show in 1986, when she was 15, the band was already past its peak, but it didn’t bother her; that was only the music. “I was mostly there for the people,” she said.

It’s harder than you might expect to buy Rosie Schaap a drink, at least in South Slope. Bartenders tend to fill her glass on the house. (The hardest part of being a regular, she says, is meeting the credit card minimum.) And of course, drinking with Ms. Schaap in South Slope means sharing her attention with just about everybody else. She handles this with aplomb. On our way from South to Quarter Bar along Fifth Avenue, we passed Hector, who had a beret and several missing teeth and was in the middle of doing his laundry. Ms. Schaap greeted him warmly. He is, she said, “the real mayor of the neighborhood.”

Quarter Bar was empty, and we both ordered Two Bits, the house special bourbon cocktail. It has two kinds of bourbon, a touch of amaretto (“One of my favorite secret ingredients,” said Ms. Schaap—it sweetens without simple syrup), Angostura bitters, Peychaud’s bitters and an orange twist.

Ms. Schaap knows cocktails and she knows bars, but she considers the two mostly distinct. “They have almost nothing to do with each other, from my experience,” she said. “I love cocktails, but most of my bar life has not been about cocktails.” Ms. Christensen, her novelist friend, put her up for the Drink columnist job at the Times. The paper had asked her to try out for the job herself, but she had a better candidate in mind.

“It was just sort of an instantaneous realization that it should be Rosie Schaap,” Ms. Christensen told me later. “Rosie cared about drinking, as opposed to mixology,” Ms. Christensen explained. She was more interested in memories, associations and context. “She was really the person in all of New York City who was perfect to write this column.”

After what Ms. Schaap called “an amazing reality-TV-show-esque audition process,” the Times agreed.

“My mother was a real whiskey sour person,” Ms. Schaap said. “Just as Parliaments were my first cigarette because I stole them from her, a whiskey sour was probably my first cocktail, because I probably snuck a few sips of hers when we were in a restaurant and she went to powder her nose.” Because a whiskey sour reminds her of her mother, it makes her think of “a New York I didn’t live in,” she said. “A really glamorous late ’50s or early ’60s Truman Capote New York, where people wore great hats and had cigarette holders and, you know, scattered home in the daylight up Park Avenue at 6 in the morning.”

Pints of Guinness, of course, bring her back to Dublin: she spent one college summer drinking at a “smoky and cozy and welcoming” pub called Grogan’s and learning to love craìc, Irish bar banter. Manhattans are a tribute to her late husband, Frank Duba, who died in 2010: “I first drank Manhattans in Frank’s company,” she wrote in one column, “and now I drink them in his honor.” Jack Daniels was her preferred liquor as a teenager, and now it makes her sick: she hasn’t been able to drink it, she writes in the book, ever since the night on the Grateful Dead tour when she did 21 shots and woke up “on a greasy, flattened stretch of carpet in that cheap motel room in Inglewood with a nearly rigid disk of my own shit stuck to my backside.”

When Ms. Schaap gave up life as a Deadhead after 99 shows, she left Santa Cruz and went back east to go to Bennington. She had imagined herself pursuing an interdisciplinary mélange of Marxism and folklore and feminist poetry, but instead received a “very, very canonical English education.”

As she began to tell a story about a Blake seminar, Quarter’s owner, David Moo, arrived and joined us. He makes the Manhattans that Ms. Schaap wrote up for the Times. They compared notes on a mutual friend who had helped Rosie with a story for Lucky Peach. But it was time to move on. Trivia night was fast approaching.

Freddy’s, our last bar, is a neighborhood transplant. After a long fight against the encroachment of the Atlantic Yards, the bar ceded its longtime home in Prospect Heights and decamped to South Slope in the spring of 2011. As we approached, a friend flagged us down from across Fifth Avenue—John Eichleay, a musician Ms. Schaap got to know while working on her book at the neighborhood coffee shop. Usually local camaraderie is nice, but Roots Café eventually got “too friendly” for writing.

“I feel like the whole neighborhood has been with me through the whole project,” she said.

After college, Ms. Schaap wound up in the English Ph.D. program at CUNY. In retrospect, she wasn’t really ready for grad school, and she began a period of “very heavy drinking.” Still, she loved teaching. Her job at the Borough of Manhattan Community College was right down the street from Puffy’s, one of the first bars she loved in the city. She’d grade papers over Guinness after class.

But the Ph.D. didn’t work out. Ms. Schaap fell into a succession of jobs that were to varying degrees menial and meaningful. She worked as a community organizer for New York City Coalition Against Hunger; she got ordained as an interfaith minister; she served as a Red Cross chaplain after 9/11; and she was an editor at the inspirational magazine Guideposts when Riverhead bought Drinking with Men in 2008.

These are the jobs happening in the background of the book, which follows Ms. Schaap figuring out how to live the rest of her life while relying on the grounding presence of her barroom communities. Seeking literary precedents for the kind of story she wanted to tell, she found that drinking books by women tended to be tales of recovery. Mary Karr, Caroline Knapp—she had “tremendous respect” for their work, but hesitated to write that kind of narrative.

“Inadvertently,” she said, “they kind of confirm this message that ultimately this is a bad life for a woman ... I did some dumb things. There were nights I drank too much. I thought long and hard about whether I had a problem.” Tonight she’s had a Guinness, a shot of Jameson, a cocktail, and another Guinness. That’s “pretty good” for her, she said, these days.

“If I ever had an addiction, it wasn’t to alcohol,” she said. “It was to bars.”

editorial@observer.com