‘Sweethearts’ Is Jordan Weiss’ Semi-Autobiographical Ode to John Hughes — Just Don’t Call It a Millenial Comedy

If “Rebel Without a Cause” took teenagers onscreen seriously for the first time beginning in the 1950s, then John Hughes helped revitalize them once more as a full-fledged genre in the 1980s. The new film “Sweethearts” celebrates both moments in cinematic history.

“Sweethearts,” whose title is a nod to the ’50s lingo of high school sweethearts in the era of going steady, is “Dollface” creator and “Freakier Friday” screenwriter Jordan Weiss‘ directorial debut. The filmmaker co-wrote the script with her real-life best friend Dan Brier; Weiss and Brier’s relationship also in part inspired the not-quite rom-com about Jamie and Ben, two college freshmen who make a pact to break up with their high school sweethearts over Thanksgiving break… and realize that they might actually have feelings for each other instead.

It’s fitting that Kiernan Shipka, a breakout of ’50s-set series “Mad Men” who later went on to lead the ’80s-aesthetic “The Chilling Adventures of Sabrina,” was the first star cast in “Sweethearts.”

“She was always who I dreamed of to play Jamie … She’s such an amazing performer onscreen, but off-screen, she’s really, really smart,” writer/director Weiss told IndieWire about working with Shipka. “She had such great things to say about how she wanted to bring Jamie to life, and I just knew she was going to be such a great leader for a set. And as a first-time director, I just knew she was going to be such a dependable, amazing energy to have.”

But who could balance out Shipka’s Jamie? According to Weiss, for whom the character Jamie is a surrogate of sorts, the film was “going to live and die by the chemistry between her and whoever played Ben.”

Enter: “Booksmart” alum Nico Hiraga.

“There was no decision to be made once Nico walked out of the room. I think he got the part about four seconds after the door closed, leaving their chemistry read, because it was so obvious,” Weiss said. “[Dan and I] wrote this together. We were all also both executive producers on the film. We really knew the dynamic we were looking for … captured by our friendship in real life. And so just the way that Nico and Kieran are so different, they have such opposite personalities, but there was just this magic when they made each other laugh, even when they were just goofing around in between reading the scenes. I was like, ‘That’s them, that’s Ben and Jamie.'”

‘Sweethearts’

The cast is rounded out by “Severance” star Tramell Tillman, Joel Kim Booster, Ava Demary, Charlie Hall, and Christine Taylor.

And while the film is semi-autobiographical for Weiss, she encouraged the cast to improvise on set, especially to avoid making the script seem too “millennial.”

“I’m a big fan of improv. I’m definitely a comedy girl through and through, and I come originally from TV. TV is very democratic, the best joke wins, so I have really no ego about that. And I love when my actors make me look funnier than I am by coming up with amazing stuff on set,” Weiss said. “I tried to really encourage and foster an environment on our set for the actors to play, for them to improvise … where our actors, especially the younger generation ones who are closer to the age of the characters than Dan and I are as people in our 30s…We really wanted to make sure this felt authentic to young people”

But, she said, “We were also pretty intentional to try to avoid too much modern slang or vernacular just because I think it can date things.”

She added that like her “all-time favorite director” John Hughes, “Sweethearts” had to have a “sense of timelessness” like “Ferris Bueller.”

“I think that we were really intentional with the way that we styled their costumes and the music that we picked and the sort of slang we tried to avoid to create that evergreen timelessness,” Weiss said. “But we did definitely sit down all of our cool Gen Z actors on day one, and we were like, ‘If we have written any line in the script that makes us seem like cringe millennials, you are obligated to say so and to tell us and to work on it with us.'”

It was also important that Shipka infused the character Jamie with her own “experiences and touchstones and personal style and way of speaking” so that Jamie “isn’t just about me anymore,” Weiss said.

As for the character’s backstory, Shipka said, “[Developing a character] is always important to me, and I was lucky that in the movie there’s actually a glimpse of why Jamie is the way that she is, so that I thought a lot about. I thought a lot about our friendship and our relationship growing up, and honestly just being on set with such awesome set pieces made it very easy to feel the energy of this film while in production. It was all there, no green screen. It was very practical, and we were just having a good time.”

‘Sweethearts’

Weiss wanted to build out a ’50s-inspired idyllic town to emphasize just how much Jamie and Ben’s perspectives on where they grew up would have changed after just a few weeks away at college. It’s the rose-tinted glasses, of sorts.

“A lot of what this movie is about is when you leave your hometown and return from the first time after being away with fresh eyes, and I think that is such an interesting, unnerving sort of cardinal event of being a young adult and returning to your hometown for the first time after you don’t live there anymore,” Weiss said. “The first time you go back to your bedroom, and it’s not your bedroom anymore, it’s your ‘childhood bedroom.’ And I think sometimes it can feel like you’re stepping into a time capsule or like you’re stepping into the past, and so I thought it would be a really cool interpretation of that feeling to embrace a little bit of a retro feel in our production design and our costumes. We have a lot of 1950s touches, mid-century aesthetic touches; even the title ‘Sweethearts’ is a reference to the phrase high school sweethearts. It makes me think of like ‘Archie Comics’ and my grandparents and sockhops and ‘Grease.'”

Of course, there’s another Shipka connection: The actress led “The Chilling Adventures of Sabrina,” which literally was an “Archie” comic.

“Sweethearts” isn’t all sweet — it also captures the heightened emotions of being a teenager trying to navigate adult situations. Shipka pointed to a “blowout fight scene” alongside Hiraga that she “really loved” filming. Hiraga, though, did not.

“It was tough to do,” Hiraga said. “You’re looking at this angel [Shipka], and your voice is getting louder. It kind of makes you not too stoked. I didn’t love that.”

Yet Shipka explained that it was a real-life time crunch that led to how intense the onscreen drama was.

“There was a lightning storm situation, and we didn’t have that long to film it before set had to shut down,” Shipka recalled of the scene, “and I kind of love a time constraint or some sort of pressure. It felt like very high stakes, and when we did it, it ended up being so cathartic.”

It helped that Shipka saw herself in Jamie, too.

“I’m in my 20s, I have lots of guy friends, and there’s always that energy, for me at least, with a lot of people,” Shipka said of the “will-they, won’t-they” storyline. “I always think about the what if, even if it’s not meant to be.”

“Sweethearts” writer/director Weiss hope the film can live up to the John Hughes legacy of teen angst and love onscreen.

“[Hughes] films were so successful … because he took teenagers seriously and he took their stories seriously and I think we tried to do the same thing,” Weiss said, “even if sometimes one of the characters might be a little misguided or might be realizing something that to an adult would seem obvious, it’s still really meaningful to them.”

Weiss is set to adapt Curtis Sittenfeld’s bestselling novel “Romantic Comedy” and also sold a rom-com pitch to New Line Cinema about the NFL playoffs. She additionally wrote the “Freaky Friday” sequel, “Freakier Friday,” from “Late Night” and “And Just Like That” director Nisha Ganatra. Shipka’s “The Last Showgirl” co-star Jamie Lee Curtis reprises her original role from the 2003 film alongside Lindsay Lohan, Chad Michael Murray, and Mark Harmon.

To Weiss, “Sweethearts” is a throughline for all her projects.

“The theme of my career thus far, and the kind of stories I’m really interested in, are unconventional love stories,” Weiss said. “I think that ‘Dollface’ was a love story between a girl and her female friends, and ‘Sweethearts’ is a love story about platonic love, and ‘Freakier Friday’ is a love story for mothers and daughters.”

“Sweethearts” premieres November 28 on Max.