Love — or at least high school infatuation — works in mysterious ways. As a junior at Yale, Natalie Krinsky ’04 never expected to be asked to another high school prom. But after an admiring high school senior in Tennessee read Krinsky’s notorious column “Sex and the (Elm) City,” he was so charmed by her persona that he invited her to dance the night away.

And he was not the only one to be intrigued by Krinsky’s column about sex and dating at Yale. During her junior year, Krinsky sold a book proposal, based on her experience as a sex columnist, to Hyperion Books. Now, several of her Yale Daily News columns have been published as part of her novel, “Chloe Does Yale,” which details the romantic adventures of a “fictional” sex columnist at the University.

Despite the protagonist Chloe’s resemblance to herself, Krinsky denies that the novel is a “roman a clef.”

“It’s 70 percent fiction and 30 percent reality, and we’ll let the reader decide what is what,” she said during lunch recently in New York, where she lives and works.

But Krinsky admitted that her own experience at Yale provided inspiration for some episodes in the novel. During a vacation, Chloe finds out that her freshman-year boyfriend, Josh, is engaged.

“The Josh event isn’t true, I never dated a senior when I was a freshman,” Krinsky said. “But I did have an ex-boyfriend who happened to live in my building, and I came back and he was engaged.”

The publication of “Chloe Does Yale” is just the most recent stop on what Krinsky describes as the “wild ride” of writing the column and then the novel. Her controversial column, which broached such topics as proper blow job etiquette and the ambiguity of dating in college, generated interest across the country; some columns received more than 200,000 hits on the News’ Web site. During her years as a columnist at Yale, she was featured in a New York Times article about college sex columnists and appeared on the Today Show.

Although Krinsky wrote for her high school newspaper, she said she stopped writing during her freshman year of college. But the column reinvigorated her interest in writing and journalism.

“When I was writing [Sex and the (Elm) City], it was so much fun,” she said. “People let you in in ways they wouldn’t always do.”

Krinsky said research for her columns taught her something about the minds of men and women.

“It was so much fun going out and asking people what they thought about hand jobs or about dance floor erections,” she said. “Every single issue, you would ask a man and ask a woman and get polar opposite responses.”

While Krinsky said she would try to keep her own romantic relationships from figuring in the column, Kanika Chander ’04, Krinsky’s classmate in Timothy Dwight College, said she could see the influence of their group of friends on the column.

“We’d have dining hall discussions, and then two days later you’d see phrases we had coined in the dining hall one day appearing in the newspaper,” Chander said.

Many of the columns generated heated debate and shocked readers across the country. But at Yale, Chander said, few people were shocked by the column.

Kevin Abels ’05 said he thought the national shock value of Krinsky’s column was based on its setting at a prestigious university.

“Being in college, it obviously wasn’t shocking or surprising or controversial to me,” he said. “I think a lot of the hype had to do with the fact that there was someone at Yale writing about this sort of thing. Yale was clearly no longer an old boys’ network, a stodgy conservative place.”

“Chloe Does Yale,” written while Krinsky was an undergraduate at the University, may further undercut Yale’s “stodgy” stereotype. Krinsky first conceived of the idea of turning her column into a book shortly after she started writing the column her sophomore year. Eventually the idea of compiling her columns grew into a plan for a novel about a fictional columnist.

Krinsky had her first meeting with a literary agent in fall 2002, with the assistance of Yale journalism professor Steven Brill. With the help of her agent, Krinsky developed a book proposal that was purchased by Hyperion in March 2003.

“I started writing in June [2003],” she said. “I thought it would be a great summer job. I probably spent the first two months in absolute paralysis. I have a big problem being by myself all day long.”

When her senior year started in September 2003, Krinsky said she had 50 pages written and the novel was due Feb. 1, 2004. But Krinsky credits the social environment of Yale — and the pressure of a looming deadline — with allowing her to finish the novel close to her deadline.

“Back at school, everything just clicked,” she said.

She finished the novel on Feb. 7, 2004, at 5:46 a.m., and while she was anxious about the missed deadline, Krinsky said her editors told her that they had never received a novel so close to the deadline. But the History Department does not accept senior essays on the same schedule, so Krinsky said she had to scramble to finish her senior essay in three weeks after completing the novel.

Since her graduation in June 2004, Krinsky has been writing her second novel while working four days a week at an advertising agency.

“Traditionally, people tell me, your second novel is very difficult to begin, and they’re right,” she said.

Krinsky was close-lipped about the subject of the new book, which she said is in its “early stages.”

In the same way that the media took notice when she was writing her column, “Chloe Does Yale” has already received attention. In the Jan. 21 issue of Entertainment Weekly, she was featured in a photo spread previewing her novel.

And if any of her loyal readers wonders whether Krinsky has lost her edge in the years since she graduated, they can open “Chloe Does Yale” to the passage in which Chloe names Tolstoy as her fantasy literary paramour.

“I’m sure [Tolstoy] wouldn’t be a bad lay, in the right light,” Krinsky jokes.

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