Interview (Written): Katie Silberman

Conversation with the screenwriter of the romantic comedy Set It Up.

A Vulture interview with Katie Silberman, screenwriter of the Netflix romantic comedy Set It Up, directed by Claire Scanlon, starring Zoey Deutch and Glen Powell. Her producing credits include Hot Pursuit and How to Be Single.

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.

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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.

Here is a trailer for the movie Set It Up:

For the rest of the interview, go here.

Twitter: @katiesilberman.

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