Casebook, Mona Simpson’s sixth novel, is her first told through the eyes of a boy. Her protagonist is a 12-year-old boy, Miles, who has the makings of an amateur sleuth: He eavesdrops like crazy on his parents’ conversations and his mom’s phone calls and chats with friends, and snoops around drawers and emails. Along with his best/only friend, Hector, Miles learns the nasty realities of his parents’ divorce and begins to find out more about his mother’s new boyfriend. Miles and Hector unearth truths they can’t help but want to know: they discover receipts and weird love notes, and as they learn more about this stranger who claims to love Miles’s mom, the family’s situation changes irrevocably.
The topic of evolving familial dynamics is somewhat of a trend for Simpson. In her widely acclaimed first novel, Anywhere But Here (1986), Simpson wrote about the relationship between a mom and her daughter who move from Wisconsin to Los Angeles. Off Keck Road (2000) depicts the lives of three generations of Midwestern women. In My Hollywood (2011), Simpson explores the relationship between a composer and the nanny to her kids, an immigrant from the Philippines, and how their lives both overlap and are totally separate.
I spoke with Simpson over the phone about how she took on the perspective of her adolescent male protagonist, how she’s grown since writing Anywhere But Here, and how a surfer dude and her son helped her writing process.
The Millions: Did the plot of Casebook come to you all at once, or was it something that came slowly?
MS: That’s a good question. I think that the main thrust of the plot came all at once, but little parts of it, , details and dialogue, developed as I went along. I wanted to tell a love story, but I liked setting it within a family, a group of people for whom the romance would not be the primary interest. And I needed a way in. The narrow vantage of a son appealed to me. He has his own interests. He’s watching a love story emerge and he’s wondering, what does this mean for me?
TM: In My Hollywood and Anywhere But Here, your protagonists are female. Did you always know the character Miles would be a boy?
MS: I did always see Miles as a boy, although I recently wrote an essay about my life growing up with a single mother, and it occurred to me again that Miles’s essential stance, his protectiveness towards his mother and his suspicion of her boyfriend, was very much my own role in my family. I didn’t like how romantic my mother was; that seemed to me a liability for her job, which was supposed to be to take care of me. (I was so selfish.) I suppose I felt almost male: She was the romantic, I was the practical one. At the time, I refused any “femininity.” I wouldn’t learn how to put on makeup. I worked at jobs instead. I assessed the men she considered her romantic prospects in terms of whether they could help us financially. I understood that they could break her and that terrified me. I saw romance as bigger than I was and dangerous.
TM: So what are the challenges of assuming the perspective of an adolescent boy?
MS: Well, you inhabit these characters and there’s always a part of your own emotional complexion in it, and you just don’t want it to be inaccurate.
Those are the challenges. I gave it to a few L.A. native boys to read. And they picked up some little things, like I used the word “hearth,” and one of my students, who’s a surfer, said he didn’t think Miles would use the word “hearth,” so I took out “hearth.” He also gave me the term “rag-dolled” for the experience of being tossed around by a wave.
TM: Did you do any eavesdropping as research for this book?
MS: Well, I have children— I certainly listen to their lingo. And of course I teach as well, so I have a lot of teenagers in my life. That all seems a little more osmotic than research, but I did do other kinds of research. I talked to some private detectives.
TM: As fuel for the character of Ben O’Ryan [the private investigator Miles and Hector hire]? How did he come to be?
MS: Well, I started to write the detective, and then afterwards I talked to a few private eyes, several different kinds, to make sure I didn’t get the details wrong. My favorite was a guy here in Santa Monica. One of the things he said was that people don’t mythologize law enforcement or private eyes, or cops of any variety anymore. Then he said, “But everyone loves a fireman!” For me, that started the character. I love that character.
TM: That was such a great line.
MS: One of the P.I.s I interviewed does a lot of work on background checks for reality shows, and another did security work for celebrities, so I found some interesting stuff.
TM: Did you feel you could only set this book in California?
MS: Yes. I didn’t even consider setting it somewhere else.
TM: I loved the quote that gets repeated a lot — it’s Miles’s and Hector’s school’s philosophy: “Is it true? Is it kind? Is it necessary? Will it improve upon the silence?” When did you first come across that quote?
MS: It’s a quote used by the school my children go to. I’m a parental veteran of progressive education.
TM: What is most attractive to you about progressive education? Have you always been an advocate of it?
MS: I don’t know. As a parent, my initial instincts all led towards constraint; I liked it when my children were strapped into strollers, or settled in cribs with high walls. I favored playgrounds with fences.
I would have liked my children to attend school in uniforms. I’d have had them sitting in classrooms with wooden desks in rows, memorizing Latin poems. But it didn’t turn out that way. My kids went to progressive preschools, a progressive elementary school and a progressive highschool and I’ve ended up a believer. Their schools were strictest about how kids treated each other. They spent a lot of time talking about kindness, inclusion and respect.
TM: So did you feel any sympathy for Eli as you wrote him?
MS: I did…I felt for him because it felt like he really made a mess of things. Most of all for himself. I did have sympathy for him. Probably more than Miles had.
TM: So did you draw the cartoons that are in the novel?
MS: Oh, no! I tried. I actually really sort of tried to take up drawing while I was doing this book. And I did a lot of sketching and I have notebooks full and I managed to do a cat that we sort of liked, but overall I couldn’t…my people weren’t even close to good enough. So I actually got a kid, I hired a kid, who’s an artist, to do them.
TM: How interesting!
MS: He’s a 20 year-old I’d known for years. His name is Alexander Allaire.
TM: So you trusted him.
MS: I’d known he was a doodler. I hoped to do it myself, though, I really try to keep up with the sketching.
TM: It’s such a hard thing.
MS: I know, but it’s a very neat thing to do, too. I find I’m good at small objects and flowers.
TM: How do you think you’ve grown as a writer over the course of the six novels you’ve written?
MS: Oh, that’s a good question. I hope I’ve grown as a writer in the course of the novels. That’s probably not for me to decide, but…it’s always an interesting question for a writer, how to grow. Does one go for the huge leaps or slow incremental development. I’m not sure. Once I found that entry point of Miles’ voice, for this book — I thought of it as one little wedge of a door opening – this book flowed easily. It wasn’t an uphill slog. It wasn’t an enormous hurdle I set for myself, like, “This is going be the greatest whatever or this is going to be completely different than everything I’ve ever done before.” Casebook is my sixth novel. I’m a little more relaxed now. I’ve learned to trust the process. I read all the time and I write about what I care about most. I trust if I do that, the work will grow.
TM: It does. I would think that the first novel is the one that you feel most alienated from.
MS: Well, I don’t reread my early novels. Actually, I don’t read any of them, except the one I’m in. I read a book so many hundreds of times when I’m working on it, when I’m finished, I’m really done. I think it would be painful, because I’d want to make changes on every page.
But I think there’s a great temptation to sort of resist what it is you do naturally. Because we all want to grow. But at the same time, there’s a lot of joy and surprise in writing intuitively, not pushing yourself with a nagging mind.
TM: It’s a matter of combining both dreaming ahead and staying present, for sure. Do you feel similar to Miles in some ways?
MS: That’s a good question. Miles is suspicious. I don’t think I’m as suspicious as he is, but I’m compulsive. And I think we have a similar stance to romance. We’re both skeptical observers, but that skepticism hides a shy, protected hope. As I mentioned, I grew up watching a parent’s romantic life.
TM: Right. You were a witness to that.
MS: And I wanted different things from it than she did. I would have been happy for it to go away.
TM: What books are you most excited to read next?
MS: I’m reading Elena Ferrante, who I just love. And I’m reading the third installment of the Karl Ove Knausgaard’s My Struggle. And then just yesterday, for a short story of mine I read, I re-read — I mean I’ve read it a bunch of times, it’s just a great story — Chekhov’s novella, Three Years. Just amazingly good. It was written in 1895, and yet it’s almost an anti-love story. The woman marries a guy quite clearly who she doesn’t like and she’s quite aware of it but she thinks it’s probably the best decision for her. And he knows that she’s doing it to sort of get away from her father and her small town. And yet it’s not an arranged marriage; they do each have a choice. It’s such a fantastic story.