Set It Up’s Katie Silberman Is Here to Save the Rom-Com

Katie Silberman. Photo: Monica Schipper/Getty Images for Netflix

Love isn’t dead as long as screenwriter Katie Silberman wields her laptop. Last month, Silberman’s Set It Up premiered on Netflix to swoons as romance-starved audiences rooted for aggrieved personal assistants Zoey Deutch and Glen Powell to successfully hook up their horrible bosses Lucy Liu and Taye Diggs — or at least fall in love themselves. Set It Up was Silberman’s first hit rom-com, and next year, she’ll have two more: the girl-nerds-unleashed Booksmart, directed by Olivia Wilde, and the ultrameta Isn’t It Romantic, in which a cynical Rebel Wilson wakes up inside a warped world of rom-com clichés.

Meanwhile, Silberman’s just returned from her own honeymoon to a Hollywood that, after a decade of swatting down passionate blockbusters, might finally be ready to fall in love again. But how does the rom-com fit into a culture that’s reexamining gender roles and bewailing Tinder? And are we finally done writing scripts about cute blonde cupcake bakers with zero personality?

Congrats! You got married the week Set It Up premiered, proving love is for real.
It was crazy. It was especially fun because Zoey and Glen were at the wedding. They were such good sports to come to my rehearsal dinner with my entire family who had all seen Set It Up that day and all wanted to talk to them. They were bigger celebrities at the wedding than I was. But it was a really, really extraordinarily fun weekend. It was the highlight of my life and it will all be downhill from there.

You were an assistant. Is that where the idea came from?
I developed the script with Juliet Berman, our producer, who is a good friend of mine in real life as well. She and I both met when we were assistants, and she and I both had terrific bosses who wound up being terrific mentors. But we knew some people who were assistants to people who weren’t as great. She was more connected to the general assistant world. I was an assistant to a writer, so it was a little more isolated. She had heard so many stories about terrible experiences and great experiences and she came up with the idea that two assistants could try to set their bosses up because they know so much about them and control their schedules. Once she came up with that great idea, she and I were able to develop it and come up with a story and speak with all of our friends who were assistants, and some of our friends who had assistants, and come up with their backstories that helped inform that world. I’ve only had one boss and she was the greatest boss in the world, so getting to research all the situations that weren’t as great, I got to go, ‘My boss was awesome!’

Were you worried your former boss might think a detail in there was about her — or that people who knew you worked for her would?
I wasn’t! Her name is Dana Fox and she’s truly the kindest, most beloved person in Hollywood. I don’t think anyone would believe that, but I’ll also shout from the rooftops about how wonderful she is forever for the rest of my life, even if this movie hadn’t been made.

You were on set the entire shoot. Was there a moment when you saw the director, Claire Scanlon, add a beat that made the romance bloom?
Claire talked a lot about her experience on The Office and how they were taught to lean into the emotion of things and not always try and make a joke or be cynical. I think she had a great sense throughout the whole thing of making sure we kept the heart alive. The night that we shot the engagement party was really fun. We were on a beautiful rooftop in New York and playing the kind of music we were dancing to in the scene so they whole crew felt a little bit like we were at a party. The transition from the goofy dancing to the slow dancing, to watch Claire find those moments of them looking at each other in such an already-romantic setting. Obviously, the pizza scene was fun, seeing the two of them as they were quite literally inhaling pizza at a rate I’d never seen in my human life.

Zoey eventually threw up from too much pizza.
I was jealous. I was trying to eat the prop food the entire time and that was the one night I thought there was enough pizza no one would notice. But they were going through it at such a clip, even I couldn’t sneak a piece because we were going to run out. I think Claire was always very aware of moments that wouldn’t seem romantic, but if you catch the right look between people as they’re behaving in a real way and feeling grounded, you can start to develop those romantic moments even earlier. I learned a lot watching her find those moments in places I hadn’t expected.

Zoey said she stole you for the character: the way you talk, your hair color.
That’s true! I love romantic comedies and I grew up watching all of the old screwball ones, all the Katharine Hepburn movies, all the Rosalind Russell movies. I was hoping to write in that kind of rhythm and it was such a miracle to find Zoey, who I feel like you could put in The Philadelphia Story or Woman of the Year or Bringing Up Baby or His Girl Friday. She could take over any one of those roles so easily, her rhythm and her delivery and her timing are impeccable. It’s very kind of her to say she tried to talk like me. I also had to teach her about sports because she wasn’t as familiar with a lot of them, so that was fun to give her a crash course.

What reaction were you hearing when you told people you wanted to do a romantic comedy?
Juliet was so supportive of this the whole time. I felt like everybody really wanted to find a way to make it work because everybody loved romantic comedies so much. Producers and different studios I spoke to, sometimes the answer was, “We’d love to do this, but we just don’t see a way for it to work for us.” I believed that they wanted the genre to come back because they loved it. That was inspiring in its own way. I think I wrote the kind of movie that I wanted to watch and hoped to figure out somewhere to make it. But I do feel like when we were talking about the project, everyone’s reaction was, “We love rom-coms,” even if the second part of that sentence was, “but we just can’t make them right now.” I felt a lot of love for the genre, even if some of them were saying it under their breath like, “Don’t tell anyone I love rom-coms.”

A girl Zoey Deutch’s age has never lived in an era of big rom-coms.
I know! I feel like I’m the last generation who got to see them in theaters being truly celebrated. Maybe not the last, but when I was growing up, they were the big movie of the summer. You went to see How to Lose a Guy in 10 Days or You’ve Got Mail — even movies I love like What Happens in Vegas or Nick and Nora’s Infinite Playlist or Man Up. When I was first starting to love movies, people were psyched about them. I feel so lucky to have been a kid watching movies in that time period, to be of an era when people used it as a compliment instead of under their breath.

Was there any deprogramming you had to do as an adult after the ’80s and ’90s movies where Big Gestures make everything okay and holding up a boom box solves all relationship problems?
I just loved watching old romantic comedies because it felt like all the women in them really had things they wanted. The characters were grounded and the women really had lives outside of whatever romance they were developing in the story. [You’ve Got Mail’s] Kathleen Kelly really wants to run her bookshop and keep her business afloat. In Woman of the Year, one of my favorite rom-coms, Katharine Hepburn is a really successful journalist who’s trying to manage a relationship with a man who isn’t as comfortable with her professional success. Even one of my favorites when I was little, One Fine Day — which I feel like no one talks about! — Melanie [Michelle Pfeiffer] in that movie is a single, struggling working mother, but she had such a tangible life. You were watching real people fall in love instead of a shtick about falling in love. So many of my favorites from the ’80s, even if they included Big Grand Gestures, I wanted to watch movies where people were doing other things besides just falling in love. That’s a great bar to try to reach for in all movies, but especially this genre. I wanted to try to make a movie starring the kinds of female characters that I loved so much.

But then what makes the right guy, especially when we’re having this cultural conversation about men who pursue the wrong way? Glen Powell in Set It Up isn’t a fantasy Ken doll — he’s prickly.
Making them interesting and grounded people doesn’t mean that they’re not going to make a lot of wrong choices and mistakes. It’s funny, I have all these clear images of the women in romantic comedies, and I don’t have a strong vision of Spencer Tracy. Joe Fox in You’ve Got Mail is the ultimate because he’s smart and charming, but he’s making a lot of wrong decisions. It takes falling in love with someone and seeing himself through the eyes of someone he respects and admires to reevaluate the choices that he’s making. That’s a great moment in any rom-com. George Clooney in One Fine Day is like that. Creating male characters who aren’t perfect Ken dolls or the bad cliché of what you wouldn’t want in a partner either, any person who’s able to change and better themselves for themselves and for someone else.

Is that what went wrong with rom-coms in the mid-2000s? Characters just flattened out into cute guy meets cute girl?
I don’t know? The truth is, I truly love all rom-coms so I’m not the right person to talk about what went wrong because I saw all of them in theaters. All my favorite rom-coms are timeless in their character arcs, the way they show falling in love. But they can also be timely. They also say something about the time. Like, You’ve Got Mail is very timely in terms of the ’90s and technology and the anonymity of AIM chats. The Philadelphia Story is all about Highline society in the 1940s. When Harry Met Sally… is men and women becoming friends in this decade where women were going into the workplace. I think the best romantic comedies take advantage of showing what it’s like to fall in love in that moment, in addition to being timely. I hope that more rom-coms going forward are able to capture what it’s like to fall in love in 2018 or the coming years because it’s changing so much with technology. That’s not to say that’s what went wrong with previous ones, but when I think of the ones that I love the most, they do feel very specific.

On that technology note, all the stories about what it’s like to date as a young person are about how Tinder is ruining everything and hook-up culture has made everybody unromantic. You blend Tinder into Set It Up, but all the news sounds awful — even though people are still falling in love.
It sounds so scary! And there’s also the difference that when my parents went on a date in the ’80s, you wouldn’t know anything about the person. The amount of information you can gather about the person you’re about to go on a date with before you lay eyes on them is bonkers. So with what it’s like to fall in love with someone when you’ve seen so much of another side of them that they haven’t shared, outside of the time you’ve spent with them? That, I think, is a really interesting dynamic. I’m curious to see how it changes dating. Is it cyclical and people will be like, “I don’t want to know much about this person?” I’m so curious about how it will be for high-school students and college students and young people in their 20s going forward.

When I’ve asked men about rom-coms, they almost all have the same favorite: When Harry Met Sally…

Yeah! And we’ve had, like, a million prestigious World War II movies since it opened three decades ago. Why is it so rare to have another When Harry Met Sally…?
I don’t know! I love that that’s the movie they identify with. I don’t think it’s a coincidence that that was the movie where Nora Ephron and Rob Reiner were teaching each other what it was like on the other side. But also, that’s a movie about two really well-developed, interesting, unique people. They say “Battle of the Sexes,” and it’s not because one is a man and one is a woman, but the specific differences in perspective that they bring and what they want out of life, and each other, and how that evolves. I think that it makes total sense to me that men identify with that movie. I think it’s because the two of them are real equals, and that’s hard to do in romantic comedies — it’s hard to feel like you want these characters to fall in love with one another. In addition to the terrific writing and terrific performances—everything about it is so wonderful and perfect — it sets a high bar in terms of showing two really distinct people try to get to a place where they’re ready to yield to each other.

And Set It Up had the same production designer, Jane Musky.
Oh my gosh! Jane is incredible!

What were you dying to ask her?
I asked her a lot of sweater questions because I love the sweaters in When Harry Met Sally… so much and she was like, “That was not my arena.” I was just so obsessed with every sweater. She’s someone I talked to a lot, both in terms of asking as many questions as I possibly could, but also because she was a terrific perspective on exactly what we’re talking about: How the best romantic comedies are considered timeless, but end up being very timely. Talking about the ’80s in that movie and the concept of single men and single women in that movie living in New York, the way that they live, the kinds of restaurants that they go to, tangible things that she could put in the production design. How lived-in that world felt as they were evolving and how that made you want them to get together. I thought she did such a terrific job in this movie of showing a version of people in their 20s who are living with roommates in small apartments and don’t have the wherewithal to decorate in the ways that they want to, and then going into offices that feel like a bigger, shinier, more glamorous version of the life you’d like to be living in before going home to your fifth-floor walk-up. I learned a lot talking to her about how characters’ homes in movies like this can inform how you understand them as people and where they go when they’re not onscreen.

And Meg Ryan wasn’t a star when she did When Harry Met Sally… and Julia Roberts wasn’t a star when she did Pretty Woman. Reese Witherspoon and Sandra Bullock, all these major stars we still have today, have romantic-comedy backgrounds. It feels like we owe it to Zoey’s generation to get these going again.
Yeah! And how much of those rom-coms were about falling in love with an actress who was strong and smart and has so much presence. I totally agree. I hope that there are more opportunities for talented people like Zoey to sink their teeth into a fun role where they get to show off all of the skills that they have.

Is there an actor who you would just love to make fall in love?
I just saw that photo of Cher and Meryl Streep and it’s all I can think about now is them doing a romantic comedy together. I will work free. I will pay them.

There’s probably conversations you’re having on your side about not just making rom-coms with a bunch of white, straight people.
Absolutely. And I think the only way the rom-com will stay relevant and evolve will be to show everyone falling in love, gay or straight, different ages. I’m really excited about another rom-com that Netflix is making starring Gina Rodriguez and Lakeith Stanfield [Someone Great] that’s going to be really terrific. Just different things going on in their lives, that’s the way to keep the rom-com as prominent in 2018 as it was in the ’80s.

You’re talking about a sequel?
I haven’t been because of the wedding, so I’m really just coming back and getting bombarded with this, so I haven’t talked about it at all. But it’s been really nice to see that people might want one — that’s been really exciting. I hope that Netflix and the studios will make a hundred different rom-coms, whether it’s Set It Up or other stories that we’re telling.

You’re also making a movie called Isn’t It Romantic, which is about a woman who gets stuck in a rom-com?
Isn’t It Romantic is a really funny movie that Todd Strauss-Schulson directed — I was one of three writers on it with Dana Fox and Erin Cardillo — where Rebel Wilson plays a woman who really dislikes rom-coms and thinks they don’t bring any value to the world, has big problems with them. And then through circumstances, wakes up and discovers that New York City has turned into the rom-com version of New York City, and has to figure out a way to get out of it. It’s a very meta look at rom-com tropes and what may be silly about them, but also what’s really great about them. Rebel’s terrific.

Are there rom-com jobs that are totally over, like Cupcake-Making Lady?
You know, I feel like a lady in a rom-com should be able to whatever she wants. I’m excited to get to potentially watch rom-coms about ladies doing different kinds of jobs. My best friends are pediatric neurosurgeons and lawyers. They work at a news channel, they’re scientists who do weird blood research. I love the show Insecure, and one of my favorite things about it is the women also have these really great jobs. They’re smart, they work in financial-consulting firms and stuff, and I’m ready to see a lady doing weird petri dish science experiments. That shows you how much I know about it — I don’t even know how to describe what she’d be doing — but smart ladies. Maybe a Supreme Court clerk in a rom-com.

Ruth Bader Ginsberg’s love story with her husband is a beautiful romance.
I know! I know! I don’t know if anyone wants to watch a rom-com about anything having to do with Congress right now, but there’s so many smart, cool women everywhere that I’m excited to see the jobs in these movies expand to watch that.

I wonder if all this Congress nonsense is why people are extra-craving romance?
And joy and kindness and empathy — they’re looking for it somewhere!

This interview has been edited and condensed for clarity.

Set It Up’s Katie Silberman Is Here to Save the Rom-Com