Jordan Weiss’ Platonic Love Stories

At 26, Jordan Weiss was feeling burnt out. She’d just wrapped the first season of Dollface — the Hulu series about a 20-something reconnecting with her friends after a bad breakup — which she created, wrote, and executive produced. But instead of taking a beat to rest, all Weiss could fantasize about was putting hundreds of miles between herself and Hollywood. “I was like, ‘I need to get in the car and drive the farthest.’ And Dan [Brier] was like, ‘Hell yeah, that sounds so fun. I want to come. Let's make a road trip of it,’” Weiss tells Bustle.

She and Brier, whom she’d met in a writer’s group years before, had always been strictly platonic. But after they hit the road, their friends and family had a hard time believing they were just friends. “Every single time we posted there were people texting us like, ‘You guys are dating. You've run away with your new boyfriend.’ Our moms were like, ‘Why are you guys lying?’”

At first, Weiss was annoyed by the inquisitions. But as a consummate When Harry Met Sally fan, she was also struck by the fact that nearly 25 years had passed since the film debuted, and people still couldn’t comprehend that she and Brier were friends without benefits. So as their trip went on, they began batting around ideas for a film that would send up the classic “will they, won’t they” trope.

Now, five years after that fateful road trip, Brier and Weiss’ Sweethearts is debuting on Max. Starring Kiernan Shipka and Nico Hiraga, the film is a clever, highly comedic look at what it’s like to navigate the world as two straight, attractive, male and female best friends who genuinely just want to be friends. “To be able to get inside of my girl brain and Dan's man brain and be like, ‘Yeah, why would a guy do that?’ Or, ‘Why would a girl assume that he meant this when he said that’ was so helpful,” says Weiss, who also made her directorial debut on the film. “I think that we have this natural battle-of-the-sexes energy that comes out.”

And though Weiss and Brier’s relationship never grew romantic, their working partnership is still thriving; these days, they’re adapting Curtis Sittenfeld’s bestselling novel, Romantic Comedy — a story about a writer on a Saturday Night Live-inspired show who falls for one of its celebrity hosts — for Reese Witherspoon’s Hello Sunshine. Meanwhile, Weiss is gearing up to release her next project: Freakier Friday, the long-awaited Lindsay Lohan and Jamie Lee Curtis reboot, which will hit theaters next August. So how is she battling the burnout now?

“I should probably have a better work-life balance, but I still do that thing where I put off laundry to the point of wearing bikini bottoms as underwear sometimes,” she says. “But these days my go-tos for burnout are dirty martinis, Love Island, and hangs with my husband and our dog, Stevie Nicks.”

Below, Weiss reflects on writing Freakier Friday, psychosexual thrillers, and Danny Zuko.

While the rom-com is your genre of choice, your work tends to focus on the platonic love shared between friends. What is it about friendship that’s such an endless source of inspiration for you?

I find it easier to write about my personal experiences when I’ve had a little bit of distance from them. I can look back on the time in my life [that inspired] Dollface and Sweethearts, and it was when my friendships really were the most impactful, important relationships to me. But it might be harder for me to sit down and write the movie about meeting the love of your life because I only got married last year.

I also love the structure of a rom-com, and it’s daunting because there have been so many amazing movies made in that genre, so I’m often looking for a slightly different way in. Or a door that I can walk through that’s maybe been walked through a few less times.

Something I think that also differentiates this film from others in the genre is that it’s just as much “com” as it is “rom.” Kiernan and Nico are both hilarious in it, but you also have a murderer’s row of comedians in the supporting roles.

I obviously idolize Nora Ephron, and I think people forget she literally has Dave Chappelle playing Tom Hanks’ best friend in You’ve Got Mail. Surrounding your romantic leads with comedians and people who can really bring that improv or a different infusion of energy is a way to make sure you’re making a movie that, while sweet, is still hitting really jokes. But I think our supporting cast and the comedians — specifically like Chloe Troast, Stavros Halkia, Caleb Hearon, Zach Zucker, Sophie Zucker, and Joel Kim Booster — really helped create the tone of the movie.

There’s also one recurring joke in the film, that I can’t not ask you about. Without giving away too many spoilers, can you please elaborate on the origin of the sex tape Nico’s character films for his girlfriend, dressed as Grease’s Danny Zuko?

I was a theater kid, but I never made anyone send me a sex tape as Danny Zuko. I wasn’t that far gone! I think you can a way you can really push comedy so that it’s big and broad but still feels grounded is to [ask yourself], “Does it feel real to the character?” So I think because his girlfriend was that sort of ridiculous theater person, it felt weirdly grounded to that person.

Between Dollface and Sweethearts, you’ve been able to mine your life for your own original material. But your next project, Freakier Friday, is a highly anticipated reboot. Was it hard to find a way into that story?

In the same way that I have done friendship love stories, to me this is a mother-daughter love story. I’m really close with my mom, and though we had those phases where we fought a ton when I was a teenager, she also had breast cancer when I was a teen. So going through that experience with her was really formative.

This was the first time I got to write a mother-daughter thing. So even though it’s not based on my own experience — it’s based on this huge popular movie from 20 years ago — I got to infuse a lot of my feelings about mothers and daughters in a way that felt like such a love letter to my mom.

Lena Dunham announced earlier today that she’s writing a Sam Bankman-Fried biopic, which I found so fascinating because it’s such a departure from the friendship-romance world you both occupy. It made me wonder, if you were to create something entirely out of your wheelhouse, what would it be?

Diners, Drive-Ins and Dives is one of my all-time favorite shows and if I were ever going to take a left turn, I’d want to do a millennial or Gen Z, girly version of it where you have a night with your friends. That being said, I loved Challengers and I think it’s definitely on my bucket list to write something a little more psychosexual like that.

This interview has been edited and condensed for clarity.