Bestselling author Megan McCafferty has had plenty of experience reaching older readers. Her five-book Jessica Darling series, which began with Sloppy Firsts (Broadway Books, 2001), was published for adults and took her heroine from age 16 up through her mid-20s, in 2009’s Perfect Fifths (Crown). McCafferty has also tried her hand at dystopian YA, with the novels Bumped and Thumped (HarperCollins/Balzer + Bray, 2011 and 2012).

Today, McCafferty told PW, she has many tweens in her life, including her own son and the children she sees each week when she volunteers at his school library. And she’s noticed that beginning around third grade, many of these younger readers are having trouble finding books that hold their interest. “I thought, what if there were a series or a book that dealt with the issues that they’re interested in?” she said. “Changes in your body, changes in your relationships with friends, changes with your parents, changes in the social dynamics – all of those things that tend to be more young-adult issues – but in a way that is age-appropriate.”

While McCafferty knew she wanted to write for middle-graders, she wasn’t quite sure what the story was. Then, one morning at 4:30, inspiration struck. She got up immediately. “I wrote for three hours before my husband and son even woke up,” she remembered. The idea? She would send Jessica Darling back to middle school.

In those early hours, McCafferty wrote the initial three chapters of what would become the first of a planned two-book prequel series. In Jessica Darling’s It-List: The Totally (Not) Guaranteed Guide to Popularity, Prettiness and Perfection (Little, Brown/ Poppy, Sept. 3), Jessica struggles with the middle-school social order, grows apart from her best friend, and lands a horrible gig as her new school’s mascot (hey, she fits in the seagull suit).

McCafferty said that while wrote the new books for younger readers – “This series is for the 10 and up reader who is meeting Jessica Darling for the first time” – she also hopes to leverage the loyalty of longtime fans. “I would love my older readers to read it and then give it to the tween in their lives and say, ‘Here’s this great girl, Jessica Darling. She was one of my favorites growing up and now you can read her, too.”

To help facilitate the intergenerational reach and generate buzz, McCafferty is working with Little, Brown on a social media campaign called “I Heart Jessica Darling” timed to the book’s launch date. Via Facebook and Twitter, the author will ask fellow writers, bloggers, reviews and fans, to name the person they hope to introduce to Jessica Darling’s It List.

Staying Power

Not only were books three, four, and five bestsellers, but Jessica and her fictional friends have spawned fan fiction, more than one Jessica Darling-themed Tumblr, and even a tribute video set to Barry Manilow's “Can’t Smile Without You.”

What gets readers hooked on this character? Ask McCafferty’s editor, Elizabeth Bewley, a longtime fan who has been a Jessica Darling fan since reading Sloppy Firsts not long after it came out. She cited Jessica’s sense of humor and personality quirks; this is a character who says her number one hobby is “thinking about things,” after all. “I also love that she is sort of a salty and sweet character,” Bewley said. “She has her moments where she is not proud of herself for decisions that she’s made. And I think that most of us can relate to that.”

Of course, writing a prequel about the younger version of a popular character, particularly in realistic fiction, comes with challenges (Sex and the City author Candace Bushnell navigated these with some success in her bestselling prequel The Carrie Diaries, which, like its predecessor, has spawned a TV series). There’s the continuity within the character’s universe, for example. McCafferty said she knows there are fans who know Jessica Darling’s world better than she does, so she tried to stay as close to the timeline as possible, “without being limited by it.”

There’s also the issue of the passage of time. Sloppy Firsts, the first book in the series, came out in 2001. If Jessica were 16 then, she would have been a tween in the 90s – something Bewley said she and McCafferty were concerned about. “We both felt that it was very important the It List books speak to a new audience and to tween girls, and so that meant that we wanted [the books] to feel very contemporary.”

To give the series a modern feel, they decided to avoid specific references to more recent pop culture and technology. That’s why when Jessica decides on a fashion-forward look for middle school, for example, she wears vintage rock band t-shirts left in her sister’s closet by an old boyfriend. “There would be some guy with a Rolling Stones T-shirt whether it was 1998 or 2013,” Bewley explained.

McCafferty has finished the second It List book, The (Totally Not) Guaranteed Guide to Friends, Foes & Faux Friends, which will be out in fall 2014. And while the It List was a two-book deal, she hopes readers will decide they want more after that.

So far, she said, the reaction has been positive – not only from bloggers and reviewers, but perhaps the harshest critics of all: two 10-year-old daughters of friends who read the book even before McCafferty turned it in to her editor. “I was nervous, because what if they tell me it’s crap?” she recalled, laughing.

But she felt reassured when one of the mothers texted her, saying that her daughter was so smitten that she was reading the book with a flashlight after lights-out. The other early reader was just as enthralled, said McCafferty: “Both of them finished it in less than a day.”

Jessica Darling’s It List: The (Totally Not) Guaranteed Guide to Popularity, Prettiness & Perfection by Megan McCafferty. Little, Brown/Poppy, $17 Sept. ISBN 978-0-316-24499-2