The Boyfriend List (15 guys, 11 shrink appointments, 4 ceramic frogs and me, ruby oliver) by E. Lockhart (Delacorte, 2005)(Listening Library, 2005). Everybody’s dumped Ruby–her boyfriend, her best friend, and all of the rest of her friends. She’s a leper at Tate Prep and the subject of unflattering scribbles on the bathroom wall. After a few panic attacks, Ruby’s parents whisk her to Dr. Z. Their visits prompt Ruby to compile a boyfriend list, the first draft of which falls into the wrong hands. Ages 12-up. Highly recommended. See more thoughts on The Boyfriend List, and read my boyfriend list.

What was your inspiration for creating this book?

I was sorting through a box of old high school memorabilia – yearbooks, school papers, picture, play programs – and I remembered this list I used to keep of all the boys I had ever kissed. (Sadly, it was not that long). Anyway, I couldn’t find the list, but I felt that lovely spark one feels when an idea appears. The Boyfriend List.

I decided on the concept for the book first – the whole thing is structured as a giant list – every boy Ruby Oliver (prep-school scholarship kid, thrift-store-fishnet-eyeglass girl) has ever had a crush on, a kiss, anything.

I really wanted to write about heartbreak. There are many wonderful novels about first love – but first love so often ends badly, and I hadn’t really seen a novel for teenagers about that. Having been repeatedly heartbroken in my day, I felt that I could write one honestly.

What was the timeline from spark to publication, and what were the major challenges along the way?

The Boyfriend List was a fast thing. I wrote a proposal, and it sold immediately. I was shocked. I plunged into writing the manuscript, and realized that I had been an absolute lunatic to propose a book structured like a list – because a novel is not a list at all. A novel that is genuinely structured like a list is a bad novel.

So I had to really work on the structure, which contains a ton of flashbacks and flash forwards. I kept a highly detailed chronology of all Ruby’s boyfriends, her every shrink appointment, the day-to-day chronology of her breakup and each key event in her transformation from popular girl to leper to famous slut.

Besides the structure, I worked on the slang. I wanted a believable prep school sound — but not one that dated the book to any particular time, and I wanted Roo to sound like a teenager with a very specific vocabulary, grounded in her school’s culture but also a little different from it. I did a lot of search and replace actions before I settled on certain words she uses – “shattered,” “completely,” “debacle,” “Ag,” and so on.

What were the challenges (literary, research, psychological, logistical) in bringing it to life?

There are footnotes in The Boyfriend List – sometimes copious one – that explain either Roo’s emotional life or some reference she’s just made. Once I had finished the novel, I had a group of teenagers (via email – my sister’s friends) take the “Freddy Krueger Quiz”– a test of their pop-culture knowledge. Do you know who Freddy Krueger is, and if so, who (or what) is he? What is AC/DC? What would a “Stephen King moment” be? That kind of thing, to make sure that the footnotes were entertaining and not annoying for my intended audience.

We cut about half of them – I had way over-written. I did the same thing for the sequel, The Boy Book. But the test was called “The John Belushi quiz.” The most entertaining answers were to the question: “Who was Freud and what was some stuff he thought?”

Cynsational Notes

Check cynsations tomorrow for an interview with E. Lockhart on her new book, Fly On The Wall (Delacorte, 2006).

When I was on the eighth grade drill team at Hillcrest Junior High (home of the Hillcrest Highlanders; now Westridge Middle School) in Overland Park, Kansas; our colors were black and blue (vaguely bruised looking) and we marched into the home gym to “Back In Black” by AC/DC during basketball season.

Cynsational News & Links

Bimonthly Showcase: Holidays and the Winter Season from CBC Magazine.

Interview with Korean American author Haemi Balgassi from papertigers.org. This is a reprint (with permission) of an interview I did with Haemi for the Web site. Also from papertigers, learn about: Saelee Oh in the illustrators gallery; the book of the month (Korean Children’s Favorite Stories (Tuttle Publishing, 2004); “A Peek at Korean Culture Through Children’s Books” by Aline Pereira; and more.

Publisher’s Weekly Best Children’s Books of 2005; see related cynsations interviews with M.T. Anderson on Whales on Stilts (Harcourt, 2005) and Jennifer Richard Jacobson on Stained (Atheneum, 2005).

Snicket, Potter Publishers Find New Ways to Reach Children Online from Authorlink.