The WD Interview: Megan McCafferty

After 10 years, five books and more than 1,500 pages with Jessica “Notso” Darling—the trenchant heroine of Sloppy Firsts, Second Helpings, Charmed Thirds, Fourth Comings and the upcoming final installment, Perfect Fifths—Megan McCafferty still gets a rush when she thinks about starting her next novel.

It’s no wonder. Sloppy Firsts enjoyed the grassroots success of debut novelists’ dreams. The third and fourth books instantly hit the bestseller lists. But even better that that: Women approach McCafferty at signings and thank her for the teen-angst nostalgia and for giving them a book neither they nor their daughters can put down; teenage girls tell her the series helped them through high school and made them realize they’re not alone. Not unlike J.D. Salinger’s Holden Caulfield or Kaye Gibbons’ Ellen Foster, Jessica Darling is a true crossover success, one whose voice is destined to outlast the “bubblegum bimbos and assembly line meatballers” she’s forced to count as her peers.

Though McCafferty assures us the Darling series isn’t autobiographical, she certainly drew inspiration from her own adolescent journals, which you can read on her blog (meganmccafferty.com/retroblogger), as well as her roles as a senior editor at Cosmopolitan and freelance writer for Glamour, YM, CosmoGirl! and other famous glossies. When she realized she truly wanted to be a writer, not an editor, McCafferty lined up enough freelance assignments to keep herself afloat and left publishing to devote herself to books.

Here, she talks about her craft, the path to publication, and the joys and frustrations of series writing.

TELL ME ABOUT THE PUBLICATION OF YOUR FIRST BOOK. HOW LONG DID IT TAKE TO SELL?

I tell people that it took six months—and 10 years. What became Sloppy Firsts came out of years and years of my own creative writing. I had all this material—short stories, personal essays, even some dramatic scenes—but it was very unstructured, just a mess of stuff. I’d always been encouraged whenever I took creative writing classes. But at the time, I’d never written anything longer than a 25-page term paper, so the idea of writing a novel was impossible to me.

When I was working at Cosmo, my co-worker John Searles sold a two-book deal. I was just blown away by that. I’d always dreamed of writing a book, and here was somebody in my midst who did it. I basically cornered him the way people now corner me and asked, “How did you do it? How can I make this happen for myself?” He said, “Well, you need to get an agent, and in order to get an agent you need to have something to show the agent. Put together the best 30 pages of your future book.”

I took 30 pages as law—it was gospel to me. I thought, well, 30 isn’t that much more than 25, I probably could do that … and so I did. I looked through all my old stuff and selected material and used that as my starting point. I rewrote, redrafted and created what ultimately became the first chapter of Sloppy Firsts. I showed that to John’s agent, who loved it, and she took me on as a client and told me to finish the first half of the book. So then I had an agent and 30 pages—that’s all I had—and a dream. Over about a four to six-week period, I wrote like a madwoman. Then we kind of worked it and shaped it, and four months later it was sold to Crown in a two-book deal, based on the first half. We signed the deal in the winter of 2000 and I finished writing it a few months later. It was published in September 2001. The whole thing—from “oh my God how did you get a book deal?” to having my own book deal—was about a year.

WHEN YOU WERE WRITING THE FIRST NOVEL, DID YOU IMAGINE IT AS A SERIES? DID YOU PITCH IT AS A SERIES?

I played up Jessica Darling’s potential as the star of a series, but only in the broadest, most hypothetical sense: “If Sloppy Firsts is successful, I’ll write three more books about her high school years!” The irony is, that’s exactly the type of series I avoided writing. I definitely didn’t visualize a series that would take her to college and beyond. Those decisions came gradually, as it became clearer to me with each book that there was great potential in exploring Jessica’s development as a person—and a character—over an extended period of time.

CAN YOU TALK A LITTLE BIT ABOUT YOUR EARLY RELATIONSHIP WITH YOUR PUBLISHER? WHAT COMPROMISES, IF ANY, DID YOU MAKE?

The title really served as a litmus test for potential publishers. I was offered more money by a very famous editor, but one of the first things she said to me was that the title was “depraved,” and would have to change. I remember thinking, If she didn’t understand that it’s a joke, how do I know that she’s going to understand a lot of the other jokes in the books? And what else is she going to ask me to change? Whereas one of the first things [editor] Kristin Kiser said was, “I love the title. It’s hilarious.” And so that was it. I was like, “I love you. You’re great. You get me.”

But she also really understood that I was aiming for this crossover market—that if I wrote the book with enough humor and heart and intelligence, it would appeal not only to girls who are still in high school, but also to those who graduated years ago and have a fondness for teen angst. She absolutely understood that from the very first meeting.

I think that because I chose the right editor, it really made everything else so much easier. She knew exactly how to tell me what I needed to know. She was very direct, and I admire direct. She was right all the time. In the rare cases I did disagree, she respectfully listened to me and said, “OK, I see your point of view.” I really valued her input.

Crown never told me to change my vision for the series or the individual books. Anything Kristin ever asked me to change always made the books better.

YOU’VE OFTEN SAID JESSICA IS THE MORE GUTSY HIGH-SCHOOL GIRL YOU WISH YOU COULD’VE BEEN. AS YOU BEGAN TO WRITE, WAS IT DIFFICULT TO NOT MAKE THE CHARACTER TOO WISE, HIP OR PERFECT?

Not too perfect—that wasn’t a problem because I think perfect characters are boring. Who would want to read about somebody who has it all together?

Sometimes I had to resist the urge to make her too clever for the sake of being clever. I had to jettison jokes that were out of character for her. But overall I think the way Jessica acts and speaks is fitting for someone who’s as hyper-intelligent and overanalytical as she is.

LET’S TALK ABOUT THE MAJOR SCENES IN THE BOOKS. DID YOU SPEND A LOT OF TIME CONTEMPLATING THEM BEFORE YOU STARTED TO WRITE?

I think about all my scenes. I do so much revising as I go along; I wonder how I could write books if I hadn’t grown up in the computer age. I think I’d be a very different writer. I find myself cutting and pasting, changing things around and deleting whole paragraphs constantly.

I don’t necessarily think I put any more thought into [major] scenes than I do to any others. To me, they’re all important. Every scene should be essential; there shouldn’t be anything in there that doesn’t contribute to the plot of the story in some way.

PLOTTING: PLANNED OR SPONTANEOUS? DO YOU OUTLINE MUCH?

Very briefly—not any kind of formal outline that you learn in English class. I have to know how the book ends. If I don’t know how the book ends, then I don’t know what the point of the book is. I often write the last scene very early in the process, if not first. And then I have very strong ideas for certain plot points along the way. But how I connect those dots to make it to the end is very intuitive and spontaneous.

Often I’ll be in the middle of a scene and a character will just kind of walk in as I’m writing and I’ll have to figure out, Why is Sara showing up here? Well, she’s clearly going to annoy Jessica. Why is that happening here? That’s kind of the magic of writing, and that’s what keeps it exciting for me.

WHAT’S THRILLING ABOUT SERIES WRITING FOR YOU?

The characters have aged 10 years between Sloppy Firsts and Perfect Fifths [slated to be published in April]. So that requires a maturation of tone, content and format. And by having Jessica and everybody else get older with each book, I’ve had this unique opportunity to explore how personality traits develop over time. From start to finish, you can see how 16-year-old Jessica is the same and how she’s different from the 26-year-old Jessica, and how core traits like her intelligence and tendency to overanalyze manifest themselves over time. I didn’t intend for it to happen that way, but I’m thrilled that it has because it’s not just the “same old, same old” with every book. I couldn’t write the same book over and over again.

WHAT ARE THE DIFFICULTIES? I IMAGINE WRITING FIVE VOLUMES OF JESSICA CAN BE A LITTLE LIKE BECOMING ROOMMATES WITH YOUR BEST FRIEND: YOU LOVE HER DEARLY, BUT YOU START TO GET A LITTLE SICK OF HER.

I never wanted it to get to the point that I was sick of Jessica. I always told myself I’d stop writing about her when I felt her story was finished. And with Perfect Fifths, I know I’ve written an ending that will hopefully satisfy my readers. I’m definitely satisfied. I think it’s a very fitting conclusion to her story.

That said, I think the most challenging part of writing this untraditional series is making each book stand on its own. It may sound funny, but every time I have a new book coming out, I get e-mail from readers who bought it without knowing there were other books that preceded it. It’s challenging to write characters consistently over the course of five books that take place over 10 years. Everyone changes, yet there have to be some aspects of their personalities that stay very true and constant from book to book. That’s been the most challenging, but in a good way. I think it has pushed me as a writer.

YOU VERY DEFTLY SUMMARIZE EVERYTHING THAT HAPPENED IN PREVIOUS BOOKS AS IT’S PERTINENT TO WHAT’S HAPPENING IN THE PRESENT OF THE STORY. HOW DIFFICULT WAS THAT?

So hard. Because I did not want it to be like Sweet Valley High, where they just cut and paste paragraphs about the aquamarine eyes and the golden hair … I didn’t want to bore my most devoted readers, who are thinking, of course we know all this!

I was always told by my editor that you can’t assume. She would say, “Look, I’ve read all these books very carefully, and I have to be reminded from book to book what’s happened before. You can’t assume everybody knows everything.” So to do that in a clever way—or at least a way that doesn’t bore the readers who do remember what’s what, or those who are reading the series over the span of a month—is very challenging. I also had to decide on the key points in the story that absolutely needed to be told.

YOU PLANNED TO STOP—OR AT LEAST BREAK FROM—JESSICA AFTER SECOND HELPINGS AND STARTED AN ENTIRELY DIFFERENT NOVEL, BUT PICKED THE SERIES UP AGAIN AFTER A DREAM. CAN YOU TELL US MORE?

When I was finishing Second Helpings, I found out I was pregnant. I thought, this is good: I’m finishing this book; I’m going to be a mother; I’ll take some time off; I’ll figure out what I want to do next.

I think I took off the rest of my pregnancy and about a year after that—the first year of my son’s life. It wasn’t really by choice; I just couldn’t even string two sentences together. I tried writing this book about a singer in a wedding band, but realized I only wanted to write the book so I could have an excuse to sing with a wedding band as research. That’s not a good enough reason to write a book. And so the beginning of this novel was terrible; I ended up salvaging it by writing a short story that ended up in an anthology.

I was a year and a half into this break when I had a dream. In the dream, I was telling my agent that I was going to write a third book about Jessica Darling. It was just a very practical conversation I was having: It’s going to cover three years instead of one, it’s going to cover her college years, it’s going to be called Charmed Thirds … and I woke up from the dream and was still suffering from a motherhood lack of sleep. I had to call my agent and ask, “Did I have this conversation with you about this new book I’m writing?” And so I took off. I took notes on it. I thought my subconscious was telling me what I was doing next.

WHEN DID YOU KNOW SLOPPY FIRSTS WAS A BIG DEAL? TAKE ME BACK TO THOSE FIRST WEEKS ON THE BESTSELLER LISTS.

I feel it most at my signings, when I hear from readers who tell me how Sloppy Firsts got them through high school. And that Jessica Darling made them realize they’re not alone. That’s when it really hits me; otherwise, I’m very detached, in my office, plugging away at these books.

The first time I had a signing where it was more than just my friends and family who showed up, I thought, wow, these are strangers. These are just girls who like my books. That struck me: Not only did I publish a book, but it’s a book people actually read and care about, and want to tell their friends about.

I didn’t make The New York Times bestseller list until Charmed Thirds, and then again for Fourth Comings. It gave me a certain validation, and it certainly helps position me for future books, but it’s not something I think about on a daily basis.

Sloppy Firsts was really a very word-of-mouth phenomenon; it’s been out for seven years and it still sells as well as when it first came out, if not a little better. It didn’t have the benefit of a splashy advertising campaign or extensive media coverage. It didn’t have a movie tie-in or anything. And yet it continues to sell well because readers love it enough to tell their friends about it. That kind of grassroots success is something I’m very proud of because I don’t know how often it happens.

DO YOU STILL GET AS MUCH OF A THRILL FROM IT NOW?

I definitely do. I went to The College of New Jersey last week and spoke to a room full of college-age women. I really get such a high talking to them and answering their questions, and seeing how excited they are about the books, and reading in general. To be a part of that is something I’m just so proud of. I’ve created this character that’s inspired them to come out on a Tuesday night and listen to me talk for an hour, when there’s so many more interesting things to do.

HAVE YOU EVER GOTTEN ANY BACKLASH FROM PARENTS, TEACHERS OR LIBRARIANS BECAUSE JESSICA—AS A TYPICAL TEEN—DOESN’T SHY AWAY FROM CRASS LANGUAGE AND EXPERIMENTATION WITH DRUGS OR SEX?

Not nearly as much as I thought I would. What minimal backlash I’ve gotten has been far exceeded by the amount of e-mail and face-to-face interactions from parents and librarians, who thank me for writing a book their daughters and students can’t put down.

JESSICA’S HAD A RANGE OF SEXUAL ENCOUNTERS, FROM ROMANTIC AND TRUE TO CHEAP AND INEBRIATED. HOW DO YOU APPROACH SEX SCENES AND KEEP THEM SO HONEST?

The awkward and icky ones are easier to write than the sincere ones. It’s easier to play these scenes for humor than it is real emotional depth. It’s very difficult not to resort to softcore clichés. I try to think about the characters and how they would see and feel the experience, and try to express it as they would.

I took a lot of time writing Jessica’s de-virginization scene, only because it had been built up so much in the first two books. I knew this was a moment that was going to be important to my readers and to the story. It needed to provide a contrast to all the baser sexual activities that were depicted throughout the books—usually by the other characters, and not Jessica—but it needed to say, “this is real.” She’s losing her virginity, she’s a teenager and she’s the heroine of the novels; I wanted to make sure it was tastefully and respectfully done, but not too precious. It was a very tricky balance.

I’VE READ THAT THE 2006 INCIDENT (IN WHICH HARVARD STUDENT KAAVYA VISWANATHAN APPEARED TO PLAGIARIZE YOUR MATERIAL) DIDN’T AFFECT YOU AS A WRITER. IN LIGHT OF HOW OPEN YOU ARE WITH THE OLD JOURNALS ON YOUR BLOG AND THE LEAKING OF STEPHENIE MEYER’S MANUSCRIPT ON THE INTERNET, WHAT ARE YOUR THOUGHTS ON INTELLECTUAL PROPERTY IN THE DIGITAL AGE?

Plagiarism has been around far longer than the Internet. In fact, I had a poem published in Seventeen magazine when I was 15 years old. About a year later I was informed that there was a girl who used that same poem to win a statewide poetry competition in Alabama. It took months for people to put together that this had happened. Whereas in 2006, thanks in part to the Internet, the first reader e-mailed me within a week of the same transgression. So in many ways, the Internet makes it easier to break the rules, but it also makes it easier to get caught.

ARE YOU STILL NOT TALKING ABOUT WHAT YOU’RE WORKING ON NEXT?

I’m so focused on finishing Perfect Fifths, that’s where all my energy is going. But I can say that I have a very intriguing concept—I’ve been calling it my dystopian high school sex comedy—that I need to nail down.

Right now it’s sprawling all over the place. It could possibly be a series. I’m very excited. It’s something I’ll be working on in early 2009, and I’m hoping it will become public shortly after this article is published.

I thought I was going to take a lot more time after finishing Jessica. I thought I was going to need a year; I’ve been writing about her for 10 years now. But I think part of the reason I’m not so sad is because I’m already very encouraged by this new idea. I have a very long pre-writing process where I’m jotting down ideas in a notebook and ripping out relevant newspaper articles—a long fact-finding mission. I feel like now that I know what [the next book] is, I see stuff all the time. It’s like a heightened awareness. I’m now attuned to everything on this particular topic. [WD]

What's on Megan McCafferty's bookshelf? Click here to find out.