How Booksmart Screenwriter Katie Silberman Wrote the Movie’s Rom-com Ending

Photo: Francois Duhamel/Annapurna Pictures

If this were the mid- to late-1990s, a movie about Katie Silberman would star Meg Ryan. She’d wear a sweater set, maybe she’d be a copy editor, and maybe, after a series of romantic foibles, she’d end up with John Cusack (only because this is the mid- to late-1990s, and Mark Ruffalo hasn’t arrived on the scene yet). Silberman has that ineffable Meg Ryan character-ness: brainy and articulate in a way that seems impossibly glamorous but also very, very relaxed. She punctuates sentences with phrases like “holy smokes.” She’s the kind of person you want to be your best friend right now, immediately and forever.

Maybe that’s what made Silberman so well-equipped to finish writing the screenplay for Booksmart, a movie that is, above all else, about two women in serious, complicated, platonic love. She worked with Olivia Wilde to craft the movie in the style of Mean Girls and Fast Times at Ridgemont High and Clueless. (“I really am just a full Amy Heckerling GeoCities account,” she tells me.) In Booksmart, best friends Molly (Beanie Feldstein) and Amy (Kaitlyn Dever) attempt to infiltrate their first and last high-school blowout, armed with matching jumpsuits and belt bags, pepper spray, the Lyft app, and Burt’s Bees. The superficial plot of the film twists and turns around this party caper, but the deeper story hinges on something else, something Molly and Amy don’t like to talk about: Even if they make it to the party, it won’t change the fact that they’ll soon find themselves on difference campuses, surrounded by different people, miles apart. “There are so many songs and movies that are mourning the loss of a romantic love, or a change in a romantic relationship,” Silberman says. “There aren’t very many for the platonic relationships. In high school, your best friend is like your soul mate. She’s your first real love … Having to change is so heartbreaking in a way.”

At the sunny Gramercy restaurant Upland, Silberman is peak Meg Ryan with a group text: She’s wearing loose denim overalls and a striped tee. She smiles devilishly when a pizza and salad arrive at our table and it becomes clear that our server has a different idea about what constitutes “too much pizza for two people.” Instead of a nameplate necklace that says “Katie” in cursive, she has one that reads “Booksmart” in block letters hanging at her collar. Over the course of lunch and an Aperol Spritz, Silberman explains how the Booksmart script went from the Blacklist to the screen.

Let’s start very generally: How did Booksmart come together?
This script had actually been around since 2009. It was first written by two really talented writers, Emily Halpern and Sarah Haskins. It was on the Blacklist in 2009 and I had heard about it then, and then I’d heard about it again in 2015 because another really talented writer, Susanna Fogel, took a second crack at it. I heard about it in a more real way in 2017, when the script was at Annapurna, and had Olivia Wilde attached to direct. They were looking for a writer to come on and re-crack it with Olivia because she had a ton of ideas and a really specific vision.

When you get an email like that, you’re like, This is a trap. I’m going to show up and someone will take my kidney, because it’s too good to be true.

What is the process of coming onboard and taking a pass at someone else’s script?
It totally varies. Sometimes it’s just punching up jokes, or adjusting dialogue or characters to the people who have been cast, or giving a certain character a past. Other times, it’s building from the ground up. Emily and Sarah, in their original draft, originated the concept of two best friends named Molly and Amy who were really smart in high school. Susannah Fogel added so much: She made Amy queer in her draft, which was then something we got to really run with. Once we realized that their worldview would be kind of cracked open by them realizing that they were the only ones who chose between fun and studying, and that everyone else did both, then we were able to relook at the whole story.

From the conversations I’ve had with a lot of the cast, it seemed like this was really a living, breathing script — I’ve heard a lot of them say they came in and read for one role, and that you then worked their own personalities or tastes into those characters.
We had a script that we really loved, and then Olivia and Allison Jones, our casting director who’s responsible for everything we’ve ever been happy about, cast this group of people that were so much better than the roles as they had been originally written. We really got to kind of adapt all of the characters to those actors. When Nico Hiraga and Eduardo Franco come in, you’re like, Oh, you are so distinctly who you are; we’re just going to make Theo and Tanner you guys.

It also seems like you had a lot of alternate jokes and alternate punch lines ready on the day of shoots.
It was nice because we felt so confident in what we had on the page, and they would nail it so quickly. The chemical equation of the set and the weather and what they were wearing and watching them interact. Some of them are such phenomenal improvisers; they brought so much themselves that I was so excited about because I was like, My mama will think I wrote that and it’s brilliant! And Olivia set such a tone for all of that. Sometimes when you’re on a set and everybody is improvising, it feels chaotic because you’re like, “What are we doing? If it’s changing this much does anyone have any idea what it is at the core?” She so clearly did, and it made us all feel so safe in knowing what it was. Nico and Victoria, who played Ryan, wore all their own clothes, like that’s how much freedom we had.

Photo: Francois Duhamel/Annapurna Pictures

What did you see in those first meetings with Olivia? What did you trust about her vision?
When she [described Booksmart as] “Training Day for high-school girls.” It was in this context of thinking of high school as war. She said this, and I think she’s so right. That it’s easy for adults to accidentally condescend and patronize how intensely young people feel things. But when you’re in it, everything does feel that heightened and intense, not only because it’s the first of so many things, but just, like, everything is that intense.

Our pitches lined up in that we both really wanted to respect Molly and Amy, but we wanted to ground them in their intensity. I think a lot of times, smart girls are seen as only intense academically, and when we first talked about Molly, the phrase we kept using was that she used a titanium bite guard — meaning that’s just how intense she is in her life.

I actually thought a lot about Molly on Insecure. That was one of the first characters that I’d ever seen that had just a phenomenal job and was really smart, but it was not really referenced ever. She had work drama at her law firm, but her character wasn’t, like, “the smart one.” She’s just a member of their friend group, and she just happened to have this great job. Watching that, I was like, that’s what my friend groups are like! Someone’s a doctor and someone works at an investment bank, but I think of them just as part of our social circle. Their brilliance isn’t always their defining quality, or their only quality.

It’s interesting talking to so many people about this movie because it seems like everyone sees themselves as a Molly. I wondered what you thought that meant.
I think, honestly, a nice aspect of Molly’s arc is that she realizes how much she has to learn. Everyone, male or female, at whatever age, has hopefully gone through a phase where they realize they thought they knew everything and didn’t, or has gone through a phase where they were putting people in boxes or put themselves in a box and realized that other people could be multidimensional.

We like to say it like astrology: I’m Molly under an Amy moon, with a Jared rising. That’s who I was in high school. Who did you think you were, when you watched it?

I was totally Molly.
I also think people want to be Molly. They want to have that drive and passion and ambition, which I think is a testament to Beanie and the way she played it.

Maybe I’m a Molly in some ways, but I have so many Amy qualities too. Sometimes I’d rather hang back and be more passive.
I can be a total Jared. I can really go overboard in terms of gift-giving, but also just being like, “Is everybody happy? Are we all good?” I need someone to tell me to calm down sometimes.

Tell me more about 17-year-old Katie Silberman. What was she like?
I feel like I really was a Molly, in that I had wonderful friends, and I had fun with them, but I did not do a lot of social stuff. I was the friend who would drop everyone off at a party, and then be like, “Have fun!” and then drive home. It’s because I had convinced myself that I was a serious person: I was focused, and I loved school. It wasn’t until my 20s that I realized that everyone who had partied and had fun was much smarter than me, and doing much better than me. I was forced to acknowledge that it was probably out of fear and insecurity, as opposed to any responsibility. So when I pitched the idea [for Booksmart’s script], it was what I wished had happened to me in high school.

What I appreciate about Booksmart is that it’s hard to apply the stereotypes that usually provide the framework for movies about high school; Nick is hot and popular, but he’s also a big Harry Potter nerd.
It’s so easy to project the idea of the mean cool guy onto [Nick], but he’s just like — the life of the party. He really is nice to everybody. He’s a lovely, much smarter guy than you would give him credit for because he can be kind of a ding-dong when it seems like he doesn’t take anything seriously. When Olivia and I were developing it, we wanted to think, What is the easy cliché for all these characters? The dumb jock, or the rich kid, or the wild girl, or all those things. How can we reveal something more about them by the end? How can they all be something more than that by the time the story is over?

One of my favorite moments is when Theo (Eduardo Franco) sees the teacher he has a crush on (Jessica Williams) walk into the party. He has that really long hair braided into two braids, and he quickly pulls his hair down. How did that come together?
We saw Eduardo’s braids when we got on set for that party. I don’t know if he had done it or if our really brilliant hairstylist Aubrey Marie had done it. When Olivia and I saw it we were like, “Oh it’s perfect,” because his hair is his power. He’s like Samson and Delilah. When he sees her, he can take it out to be like, I thought this was a night for my boys. And now it’s become a true romantic moment. But that was the kind of fun stuff we were coming up with as the party was happening.

The way he performs it is so intentional, it’s great. The tone of the evening has changed; it’s no longer a night with his friends.
Right, the way he performs it is like the most serious thing I’ve ever seen, the fury with which he’s unbraiding.

Can you tell me more about writing the Triple A character? She has my favorite line in the movie, in that scene with Molly in the car on the way home. [“You know this is why people say I gave guys roadside assistance, right? I gave them a ride home, that’s all,” Triple A says to Molly after picking her up in her car. “Okay, that’s not true; I blew them. But it’s not like they ran out of gas and I showed up to suck their dick while they waited for help. We hooked up in their car. It makes sense to hook up in a car. I’m not going to, like, suck a dick at my own home when my father can walk in at any moment. Also, I want to enjoy it. Fucking sue me.”] That whole conversation seems really tricky to pull off.
That was my favorite scene to write. I felt like that was the answer I’d always wanted for those characters. I wanted to hear, in their own words, their defense of themselves. First of all, I think Triple A is a good arguer. She’s right, and she is not ashamed of [her sexuality] in any way. Like, the only thing that bums her out is that the girls see her as this cliché. [Actor] Molly Gordon is such a genius, I just loved the opportunity to let her truly defend herself in a way where you’re like, “She is right!”

The line “You think I’m gonna suck a dick in my own home?” is the funniest thing I’ve heard in my whole life.
“When my father could walk in at any moment?” I also just loved setting it up as if the twist is gonna be that none of this is true, that she doesn’t do any of this stuff with guys. But then she’s like, “Okay, but I will though.” We wanted it to be earnest, we wanted to swing for being real, but we loved to cut back just before it gets too earnest. That’s my favorite kind of bit.

This is becoming a cliché, or at least I say it all the time, but what I really like about the Booksmart script is that it does feel like Lady Bird in the sense that you could zoom in on any of these characters and have a full feature. Everything Gigi does in an hour is a movie in and of itself.
We had so much fun figuring out what the movie of Gigi’s night would be. Like, how she physically got from place to place. It would be like Fast & Furious: Hobbs & Shaw, just Gigi going from party to party. That is such a wonderful and generous comparison because what blew my mind when I was watching Lady Bird was how much I felt every person with a single line was a full character. I understood characters just as much as if there had been four seasons of television about them. Do you remember the girl who was telling the story about their priest to Lady Bird and Danny, sitting on the wall? She’s like, “Anyway his son killed himself. My mom’s here, bye!” I would watch a whole movie about her!

Tell me more about writing that scene between Molly and Nick at the party.
We wrote it as a three-part evolution. You come back to them at the beer-pong table three times: First there’s Molly’s shock that Nick is so happy to see her. For Nick, this really is the ultimate recognition as a party thrower: “If I could get Molly to come, I’ve thrown the best possible party.” I remember feeling like this at parties, about the person that comes to a party when you’re not expecting it — especially the kind of preemptively nostalgic party like the last party of high school. It feels like it’s already legendary. That becomes the narrative of the night: “And we got Molly Davidson to come.”

We wanted her to be really good at pong, so the second beat is him being like, “You are fun!” which is what she’s wanted to prove the whole time. Things are going well, he’s impressed, and she’s kind of killing it at the party, which is not something that she expected.

And the third beat is when it actually starts to get kind of sexual and romantic, which is the Harry Potter moment. [As a kind of pickup line, Nick tells Molly that she’s probably half-Slytherin, half-Ravenclaw.] We realized that the thing that would arouse [Molly] more than anything is someone correctly identifying her Harry Potter house.

Did you read Harry Potter? Do you know what your house would be?
Thank you so much for asking. I really like that nowadays people do half-houses, which obviously can’t happen in real life, meaning Hogwarts. I think I’m probably a half-Gryffindor, half-Ravenclaw. I think I’d probably be Gryffindor just because I would want it so bad that the Sorting Hat would be like, “Okay, calm down. You can go.”

Okay, so not to return to Lady Bird again but —
Please. I am the @LadyBirdBot.

Booksmart establishes that, for a certain generation or life experience, the big emotional third-act swing of a movie is dropping someone off at the airport before they move into the next stage of their life. In Lady Bird, it’s more dramatic, but here in Booksmart, it flips it into a joke: “Let’s go get pancakes!” How did this ending come together?
When Olivia and I were first cracking what we wanted this story to be, we realized it would have the structure of a breakup movie. One of my original pitches was like, “I want to structure this like a romance because it’s a romance between Molly and Amy. So I think we should look at a rom-com structure for how this goes in terms of treating it with that kind of value.” We always knew we were going toward the airport scene. With your best friends, you can’t just say good-bye or I love you. It was never gonna be a true good-bye. Molly isn’t able to look at Amy when she’s leaving, but she’s being so casual about it — that’s what you do when you truly love somebody. They both realize that their relationship as they’d known it up to that point was over.

It’s hard to grow up and not grow apart. It’s hard to just acknowledge that a friendship is changing in a way you didn’t anticipate.
The reason female best friends, I think, are so valuable is because of the insane intimacy and almost one-person-ness of that friendship. We used to have things in the script where it was like Molly and Amy were like an entity that just moved around together. It’s really hard to become your own person when you have that connection, and I think that’s what Amy is subconsciously pushing against the whole time, and what Molly is realizing and clinging to so tightly because she doesn’t want that to change. When you really love someone — that airport scene is about them loving each other enough to recognize that they’re gonna have to go off on their own to kind of become the full people that they want to be, which is so sad. It makes me want to call all my friends from high school and be like, “I’m so sorry that we don’t talk as much as we used to.”

How Booksmart’s Screenwriter Gave the Movie a Rom-com Ending