Filmmaker Jordan Weiss loves telling love stories—just not the kind that end with a kiss.
“I’ve made my career writing out of unconventional love stories” Weiss told Decider in a recent Zoom interview. At the age of 31, she’s already created and produced the Hulu series Dollface, starring Kat Dennings; directed and co-written the new Max movie Sweethearts, starring Kiernan Shipka and Nico Hiraga; and penned the script for the upcoming Freaky Friday sequel, which wrapped up filming with Lindsay Lohan and Jamie Lee Curtis earlier this year.
“Dollface was a love story about a girl and her female friends,” Weiss explained. “Sweethearts is a love story about two platonic best friends. And Freakier Friday is a love story between mothers and daughters.”
Sweethearts, which began streaming on Max today, followes two high school BFFs, Jamie (Shipka) and Ben (Hiraga), who start their freshman year of college together while maintaining reluctant, long-distance relationships with their high school sweethearts. Things aren’t going well, so Jamie and Ben agree to participate in the time-honored college student tradition of dumping their partners over Thanksgiving break. Turns out, that’s easier said than done. Especially when everyone—the audience included—seems to be expecting Jamie and Ben to get together.
You might say this is an anti-romance romantic comedy, and inspired by the platonic dynamic between Weiss and her co-writer, Dan Brier. “Dan is my real-life best friend,” Weiss said, adding that the pair met in their 20s. “Sweethearts was a reimagination of our younger selves, had we known each other in childhood, high school, and college.”
Weiss spoke to Decider about landing her first feature film, her firm belief that men and women can be friends, and visiting the set of Freakier Friday.
Tell me about writing and developing the script with your co-writer, Dan Brier. Is any of this story based on personal experience?
Dan is my real-life best friend. Our friendship, our relationship, inspired the dynamic between the main characters played by Kiernan and Nico. In terms of dumping a high school partner—I wouldn’t say that the events of the movie are exactly pulled from either of our lives. Sweethearts was a reimagination of our younger selves, had we known each other in childhood, high school, and college. Dan and I met in our early 20s. A lot of the fodder for the movie came from us going on a best-friend road trip about five years ago, and spending a lot of time in the car giving each other context and backstory. You know when you’re telling your friend, “Here’s what’s going on with me romantically. But to understand this, you need to hear about ten years of my lore—the first person that hurt me when I was 16—to get what’s going on now.” We were having a lot of those types of conversations, and a lot of that ended up being early story breaking hours in the car.
Did you know when you were writing it that you wanted to direct this as your feature debut?
I didn’t know I would direct it when we wrote it. I really credit that to our producers at Picturestart, and honestly to Dan, for encouraging me to put myself out there and raise my hand once we started hearing directing pitches for the film.
Can you walk me through the process of pitching the film to studios, and how it found a home at New Line and then Max? What kind of notes were you hearing from studio executives?
Our first stage was to share [the script] with our agents, who sent it around to some production companies. We took a few meetings with companies that had read and enjoyed the script. Famously, one company—and I will not name them—really wanted the two characters to end up together in the end. That felt like it betrayed what our message of the movie was. So, it was an easy choice to partner with Picturestart, who really felt like they understood the film, and embraced exactly what the script was. We had a great vibe with the team there.
Once it was with Picturestart, we went into the process of packaging it up, finding a director—which eventually, ended up being me. I put together a directing deck. We met with Kiernan Shipka, who signed on as Jamie, and then we did some chemistry reads to find Nico. Their chemistry was so obvious from the first audition. Once we had our complete package, New Line was the first place that we pitched it to. They have a deal with Picturestart, and they really flipped for it. From day one, we always knew it was going to be a New Line movie made for Max.
How did you bring the movie to Kiernan Shipka? Was anyone else considered for the role?
She was top of the list. Her agent is a friend of mine. I went to lunch with him and said, “Look, I wrote this script. I’m going to direct it. And Kiernan is absolutely who I’m picturing. She’s my first choice. She’s perfect for it. She’s so funny. Will you please read it? And if you like it, will you pass it along to her?” He was a fan of the script, and he passed it along to Kiernan. After she read it, she called me and we had an amazing initial conversation. I felt like, “Wow, not only is she beautiful and talented, but she’s also smart and thoughtful and has so much insight on what she wants to bring to Jamie and how she sees the character. She’s such a professional.” I’m older than Kiernan, and I want to be Kiernan when I grow up. That’s how I feel. She’s wise beyond her years.
I loved seeing Caleb Hearon in this movie, as a fan of his comedy–can you tell me about casting and working with him?
Dan and I were such fans of Caleb’s comedy. [We’d] seen him doing stand up. I have followed him on TikTok and was obsessed, as many of us are, with all of his viral videos. We sought him out and asked his team to have him send us an audition when we were looking for Palmer. We were struggling with that part. And then we weren’t, because the second we saw Caleb’s tape, I was like, “Done. That’s him.” I mean, we knew that we wanted to cast someone in that role, specifically, with a comedian’s background. So much of the purpose of his story is to bring levity to the film. But also, he has a heartfelt journey. I think that Caleb had such a special ability to be laugh-out-loud funny, and have so much heart as well.
For Nico—how did approach doing chemistry reads for two leads that need to have a certain type of chemistry, but not a romantic type of chemistry?
Dan and I knew, specifically, the dynamic we were looking for, because it’s honestly our dynamic. It’s this best-friend, male-female energy that we have. As soon as we saw Nico and Kiernan read together, we recognized something that we see in our own friendship. The moments as a director, that I was paying very close attention to, were how they acted around each other when they weren’t doing the scene—when they broke because they both were laughing, or when they were chatting in between takes. They had such an ease and an effortlessness around each other, even from the first time they met, that I knew I was going to be able to sell them as lifelong childhood friends.
I want to talk about the ending, because I have to say, you really had me thinking it was going to end in a romance!
I feel like we’ve also tricked everybody who saw the trailer on YouTube. All the comments are angry, being like, “Another rom-com where these people end up together!” And I’m like, “Guys, watch the movie.”
Was there ever a version where it was romantic? If not, why is it so important to you that it always be about this platonic friendship?
That was always the ending we intended. We actually started with the end and worked backwards. For us, in approaching this question, “Can men and women be friends?” Dan and I are best friends. We’re happily married to people who are not each other. We obviously believe that men and women can be friends. What we wanted to do is tell a story with an extremely happy ending. When I look at two kids who are freshman in college, for me, the happiest ending I can imagine for them, is the time and space to learn about themselves, explore, go on adventures, make mistakes, fall in love, get heartbroken. That is, to me, the richest way you can fill your college years, come of age, learn about yourself. Them ending up single felt like giving them the happy ending that I would wish for my 19-year-old self.
The inclusion of the clip from When Harry Met Sally makes it feel like this movie is, if not arguing with Nora Ephron’s film, at least in conversation with it.
When Harry Met Sally is absolutely my favorite movie. I truly am such a super fan of Nora Ephron. I feel like I am agreeing, in a new way. That movie asks the question, “Can men and women be friends?” And even though the characters end up together, you watch them be very good friends for 12 years first. I actually think that that movie is showing that, yes, men and women can be friends, even though those two characters do hit a point where they end up together romantically. With Ben and Jamie, they legitimately are friends. No matter what happens in the future, that doesn’t take away from the fact that, at this moment in time, they are friends and their happy ending is being friends. Would Ben and Jamie, if we follow their story for another 15 years, find a romantic connection in their 30s? Who knows? But it wouldn’t negate the fact that they had been friends that whole time.
Did you want the audience to, for a moment, think Ben and Jamie were going to get together?
Yeah. We felt that subverting that trope would land it more powerfully if we created a bit of an intentional mislead. The scene—specifically in When Harry Met Sally, but in the rom-com genre in general—of someone running to express their feelings, is an iconic rom-com trope that we wanted to turn on its head. So, positioning [the scene where Ben runs to Jamie’s house] right after he’s watched that Billy Crystal and Meg Ryan scene helps land the comedy when it goes so opposite of what you would normally be anticipating for that moment.
Definitely worked on me! I’m so excited for the Freaky Friday sequel, which you wrote. Did you get a chance to go to set? What was it like seeing Jamie Lee Curtis and Lindsay Lohan back in those roles?
I did. It was very hard not to fan girl when I was there. I had to keep it really cool. My joke since being on that set is: “Don’t meet your heroes, unless your heroes are Jamie Lee Curtis and Lindsay Lohan, in which case absolutely meet them because they are lovely, wonderful humans.” They have such a great relationship with each other. When you have two actors who genuinely get along, and they genuinely love and care about each other, and there is so much mentorship and reciprocity in their relationship in real life, it really comes through on screen.
As a younger, first-time female director coming off of Sweethearts, to get to observe Nisha Ganatra, who directed Freakier Friday—who has more movies under her belt and was taking on this project at a larger scale—I felt really lucky to have the opportunity to watch her work and learn from her. It made me excited to try to do it again myself. I feel really privileged that I was brought on to a project with a lot of history and a lot of people that have cared about it for the last 20 years.
Can you give me the basic plot summary for this sequel? Who gets swapped with who?
I would say that it is still definitely all of the fun of the first one, and all of the mother-daughter tension. It’s really a love story for mothers and daughters in the way that the first one was, but that breathes new life and brings in a new generation, in addition to Lindsay and Jamie. But I feel like that’s all I can say.
We do know Manny Jacinto has joined the cast as Lindsay Lohan’s on-screen husband, what more can you say about his character? How does Chad Michael Murray’s character, Jake, fit into the story?
I can say officially, on the record, that Chad Michael Murray and Manny are both extremely dreamy. Quote Jordan Weiss. [Laughs.]
