Sweethearts star Kiernan Shipka, director Jordan Weiss in convo: Fake boobs, first kisses, Easter eggs, and more

Audiences came to know her as Sally Draper, daughter of Jon Hamm's Don Draper on Mad Men, and then she earned a whole new legion of fans as teenage witch Sabrina Spellman on that Netflix series.

Now, Kiernan Shipka is at the center of the new movie Sweethearts — streaming Thanksgiving day on Max — alongside Nico Hiraga (Love in Taipei, The Power) as best friends who make a plan to break up with their high school sweethearts on the same day. But is there something more between their characters, Jamie and Ben, or are they truly just friends?

Co-written by Dan Brier and Dollface creator Jordan Weiss — who's also making her directorial debut here and wrote next year's Freaky Friday sequel, Freakier Friday, with Jamie Lee Curtis and Lindsay Lohan reprising their roles — the movie is a modern-day When Harry Met Sally..., and pays tribute to other memorable rom-coms, while also leaving its own mark on the genre. Set at the fictional Densen College, the two freshmen are ready to explore life outside of their relationships — but making the move is easier said than done.

The movie is just one of five in which Shipka appears this year, along with Longlegs, Twisters, the recently released Red One (with Dwayne Johnson and Chris Evans), and the upcoming The Last Showgirl (opposite Pamela Anderson, Jamie Lee Curtis, and Brenda Song).

Below, Shipka and Weiss interview each other about the making of the movie, Shipka's love of rom-coms, Weiss' anticipation for Freakier Friday, the day of filming that almost broke the director, their shared Curtis connection, and more.

KIERNAN SHIPKA: Jordan, you've been doing Sweethearts press for a minute and obviously have been involved with the film since day Zero. Is there something that someone has not asked you that you wish you'd been asked?

JORDAN WEISS: That's such a good question. This is such a silly thing, but I feel like no one's asked me about Easter eggs. We all have fun ones in the movie, and I love that we named the fictional college in the movie Densen College and that all of my in-laws wear Densen College swag because that's my married last name, and that Dan and I made the school mascot the Terriers because both of our dogs are terriers. I literally stole everything that said the Densen Terriers off of the set.

SHIPKA: Incredible.

WEISS: That's going to be my question for you: Did you take anything?

SHIPKA: No, I didn't take anything from set. I'm always so bad at taking stuff from set. I feel like I should know better by now. [Laughs]

WEISS: Your jacket that you wore was so cute.

SHIPKA: I know, it was cute, and I would wear that kind of bomber jacket too, but I didn't take it. Some of those things are rentals, but I don't think any of our stuff was — maybe I could have taken something, but alas, I did not. However, someone at SCAD [film festival] made a very sweet Sweethearts friendship bracelet, and I still have that. I guess what you're saying is that, basically you and Dan Brier are Taylor Swift with your Easter eggs. [Laughs]

WEISS: [Laughs] Yeah. Perfect! We really are!

SHIPKA: That's pretty amazing. But no, I didn't take anything besides the memories. I really am very unskilled at taking something from set. I think I have somewhere...I remember going to a fitting for — this is so tangential — but I remember an early fitting for Mad Men, it was maybe season 1 or 2, and I was obsessed with the fake boob things; I took one. I think until really recently, it was still in my bra drawer. [Laughs]

WEISS: "Fake boobs from the set of Mad Men sell at auction, raises $50,000 for charity." That's incredible. I was going to say my other favorite Easter egg is when they drive by the movie theater in their town, all of the movies are our favorite movies. You picked one. Nico picked one. Me and Dan picked some. They're all in the Warner Bros. family, our favorite Warner Bros. movies — so it's When Harry Met Sally..., Rush Hour, Crazy, Stupid, Love, is on there.

SHIPKA: Oh, Crazy, Stupid, Love is such a good movie.

WEISS: It was mostly rom-coms and comedies that were New Line movies. Wedding Singer. He's Just Not That Into You. That is one of my favorite Easter eggs.

SHIPKA: I think that was one of my favorite things about the movie. Were you nervous going into it? I keep talking about what an amazing energy you brought to set every single day, and you were so confident and so just good all the time that I didn't really think about the fact that this is your debut feature. Did you have a lot of nerves going into it, or were there things happening on set where you were just kind of holding it together for your actors so that we didn't know that something else was going on?

WEISS: The thing by far that I was the most nervous about — this is the big secret reveal — was meeting you for the first time. I was so nervous before our first Zoom when I knew you had read and liked the script. I was like, "At this point, she likes the script. Only my personality can ruin this." [Laughs]

SHIPKA: [Laughs] No, it made it!

WEISS: I remember being really nervous. I was like, I want to be the director that she deserves because you have done this way more times than I have, and I feel like you made me so comfortable, and I drew so much confidence from our relationship. I'm not even saying this to gas you up, but I genuinely feel like I walked onto set day one confident because I was like, I can tell that Kiernan trusts me, and I know if everyone else senses that, then they will follow her lead. I drew all of my confidence on set from the way that you made me feel. [Gives Kiernan heart hands]

SHIPKA: And I drew it from the way you made me feel, so we were basically just fooling each other the entire time.

WEISS: Okay, wait, is it cheating if I ask a non-Sweethearts-related question, Like a general Kiernan question? I remember asking Nico this on set, and I don't think I asked you: What's a dream role that feels like people wouldn't know to offer you? Nico said he wants to play a Yakuza mobster.

SHIPKA: That's such a good question. It's interesting because, over the past couple years, I've done a lot of different genres, and I really like it all. [Laughs] As I get older, I start to have more and more fun on set, and I kind of crave the variety. I've always said I really want to do a musical. I really want to sing and dance my ass off. I think it'd be so fun. I grew up just adoring musical theater and musicals.

WEISS: What?! Do you want to come see Wicked with me tomorrow?

SHIPKA: I saw Wicked six times on stage.

WEISS: Wait. It's hitting me now. I feel like the part of my brain that's now remembering this from set, of you having Theater Kid energy, was a scene in the car where you, Nico, and Caleb are in the back of the minivan, everyone had their it's-four-in-the-morning, we're-doing-a-night-shoot sillies, and you and Caleb are full on belting out, doing bits, singing songs from musicals. And I thought Nico was going to absolutely jump out of the car. [Laughs] That was the one channel that he couldn't match the energy. He was like, "I will blast my cool playlist, but I do not know musicals."

SHIPKA: That's so funny because I was just talking about that scene last night because I could not keep it together when Mr. Mendelson says to me that I've grown up or whatever, and you told Caleb to go like, [whispers with hands over her chest] "Your tits." I think that's why the cut on my face is so quick because I'm genuinely really good at keeping it together most of the time, even when stuff is funny, and that was one of the times that I just absolutely lost it.

WEISS: You really didn't break that much.

SHIPKA: Well, what was really nice about watching the movie is that I think a lot of the stuff that's happening in the movie is not funny to the characters, but it is funny to the audience, and it was really nice to finally sit and watch it and laugh at it because so much of it feels like, oh my God, my entire world is utterly crumbling in this moment, and nothing is ever going to be okay again — that's kind of how these 18, 19-year-olds feel about these things.

WEISS: A hundred percent. And I think that's why I love what you guys did. The characters are taking it seriously. I hate comedies when the characters in it know that they're in a comedy, and I feel like you and Nico didn't; you guys were in an intense drama — that was the genre you were in.

SHIPKA: Yes! [Laughs]

WEISS: Okay, on the topic of Nico, you met him for the first time in our chemistry read. What, in general, surprised you about Nico?

SHIPKA: I think it was the fact that we were dying laughing in our chemistry read and couldn't even get through the scene that made me think, This is my guy. It just felt like that instant sort of soul connection thing. He's a closet sweetie pie, though. He's got a cool boy facade, but he doesn't even pretend for a minute that he's not an angel pie. I think that surprised me because you never know. He's this cool skater boy.

WEISS: Yeah, you never know. I remember seeing him look at his phone and being like, "What are you looking at?" And he was just staring at a picture of the Golden Gate Bridge and was like, "I'm really homesick. I miss San Francisco." [Laughs]

SHIPKA: That boy loves San Francisco, and he loves his parents. It's so sweet. His soul is very pure.

WEISS: I feel like you're both very close with your families. You both love your moms. That is a Keeks and Neeks special.

SHIPKA: It's true. We're mom-obsessed.

WEISS: [Laughs] Okay. I have to ask because I feel like we have so many funny stories from the treehouse scene and the night of the kiss. Were you nervous about the kiss? Obviously, you have had love interests in other projects that you've been in. Do those scenes not phase you at all? Talk to me about the kiss.

SHIPKA: See, I don't really don't get nervous for the kiss of it all. I was excited slash thinking more about the scene leading up to it than I was the actual kiss. I don't know if it's because my first kiss was probably professional...[Laughs]

WEISS: Was your first onscreen kiss in Mad Men?

SHIPKA: I kissed someone in Mad Men. I kissed someone in Flowers in the Attic, which was Ellen Burstyn...I did not kiss Ellen Burstyn! [Laughs]

WEISS: Definitely print that.

SHIPKA: [Laughs] You can! Or you can say I've never kissed Ellen Burstyn, which is true, or Heather Graham. But I kissed Mason Dye in Flowers in the Attic. Oh! I also kissed a boy in this Hallmark movie called Smooch when I was maybe 10.

WEISS: Smooch!

SHIPKA: Smooch! I don't remember in what order it happened, but [my first kiss] definitely wasn't in my personal life. I definitely had my first three or four kiss moments on screen. Got my TV period before my real period — all the things I got prepped for before the real deal. But no, I wasn't thinking about the kiss that much, also because I don't think they were thinking about it. It felt like it was this spontaneous thing, so I didn't want to dwell on it too much because it felt almost like it was out of...curiosity and because they'd had this wild sort of night, and they were exhausted and kind of raw and sitting there. To me, the movie wasn't about this massive sexual tension and we're trying to hold each other back. It felt like it was more this curiosity that was maybe a little bit more spur of the moment or came in little energetic bursts versus a simmer throughout the entire film. There were scenes that I definitely thought about. I thought about their fight scene, and I thought about Jamie retelling her childhood trauma scene a lot, but when it came to the kiss, no.

WEISS: That scene, your big fight scene — I don't know if you could tell — that was the night of the shoot I was the most upset because I had carved out four hours to shoot that. I wanted to give you guys all the time in the world to emotionally dig into that. And that was the only night we got shut down from a thunderstorm and we ended up having to do it in three or four takes, which felt so unfair to the process and to you guys. And I think I had to run down the street and scream at the weather in the sky, but was trying to act very calm in front of you and Nico. [Laughs]

SHIPKA: Woman screaming in New Jersey. [Laughs]

WEISS: Yeah, truly. Random, guttural scream.

SHIPKA: Well, you did a good job not stressing us out.

WEISS: It was so fast. And that was the one scene from the beginning with the A.D. where I was like, "We cannot rush them; I want them to have all the time in the world to dig in on this. We are going to spend our longest night on this important emotional scene." Fully shut down. I was going to ask you: I think the world sees me as a writer, and now I'm taking on this new thing [by directing my first film]; the world knows you as an actress, but tell me something you want to take on that maybe people don't know that you want to do.

SHIPKA: I love writing and...

WEISS: I want people to know that about you because you're brilliant and smart.

SHIPKA: That's so sweet. I've been doing this for coming on 19 years, which is so wild to me. And being kind of at the foundational level of a project is something that I have been loving, so I really adore writing — I have a writing partner — and it feeds my soul. If I can tell stories that I think up and can bring them to life in some kind of way, shape, or form, assemble all the thoughts into my head on a page, there's something that's just deeply cathartic about it and exciting. I've always written in some way, even when I was a kid, and it's something that I'm getting back into on a serious level now. And I love that. I admire directing so much. Watching people like you makes me want to do it someday — I don't know when, but definitely one day.

WEISS: Start with writing, and then you'll graduate. But I think that it speaks to how you are as a performer because the first time we talked about the script, you were so thoughtful about it, and it felt like talking to another writer. I think that is part of why we connected so well and I think that's so cool.

SHIPKA: I also like writing for my characters, little journal entries.

WEISS: Did you do any Jamie character work that maybe I don't even know you did?

SHIPKA: I unpacked that bee-sting moment — it was really important to me. We all have those core childhood wounds that shape how we act as adults.

WEISS: Even though it's so stupid. Every time I watch with an audience, I'm like, this is so stupid. [Laughs]

SHIPKA: Well, some can be really silly, but our brains are super-elastic.

WEISS: That was pulled from stuff in middle school. No one was ever being made fun of for something that made any sense. It was always something so crazy like that.

SHIPKA: But I recognize that you did such an amazing job of depicting her in a way that was psychologically very interesting and accurate. There was a version of a line that was something like, "I'm so unworked," and I just kept going with it. She was quite wound up and didn't really know how thick her walls were. So I did a lot of work around that moment, and then I just let it go because that's what happens — these things happen, and then you try to lock 'em out some of the time. But that was sort of a fixation of mine, making sure that I could feel in my own body that level of...

WEISS: Her cardinal wound. Her villain origin story.

SHIPKA: Jamie's villain origin story, if you will, making sure that shame just simmered the whole time. Are you excited about Freakier Friday?

WEISS: I am excited!

SHIPKA: Were you on set for most of it?

WEISS: I wouldn't say most of it. I was writing a bunch of other things this summer, but I popped in and out of set when I could. It was nice because they were shooting in L.A., so I could pop in and out. It was awesome. It is a project that so many people care about. I think because the things I've done so far have both been original ideas of mine, it's really cool and overwhelming in a good way how many people care about this title and are so excited for it. So it definitely is a different kind of pressure, but it's my first rodeo with that.

SHIPKA: Were you a fan of the original like pretty much everyone?

WEISS: Oh, absolutely. I remember seeing it in theaters with my mom when I was 10 years old. And now we're both Jamie Lee Curtis heads.

SHIPKA: We're Jamie Hive.

WEISS: Curtisans.

SHIPKA: What should Jamie Lee Curtis fans be called?

WEISS: You're really good at this. You're going to come up with a good one.

SHIPKA: Jamie Lee Curtisans...Curtistans!

WEISS: Jamie Lee Curtistans! We are such Jamie Lee Curtistans!

SHIPKA: I would say I'm in the top .0001% of Jamie Lee Curtistans.

WEISS: She's had such a big career for such a long time, but it does feel like she's in a really cool moment right now with Emmy and Oscar. It's so amazing to see her just in her full...Curtistan moment. [Laughs]

SHIPKA: When I was working with her, there was one day where we were all going to go have lunch and asked if she wanted to come. She was like, "No, I just kind of want to chill here and put my legs up the wall." She knows exactly what's good for herself in a moment and is able to then just give her entire self to a project and the people around her. She is so wise and so grounded.

WEISS: You've been in so many movies, so I'm really hesitant to say this, but would you say this is the most rom-com that you've done? I feel like this is your main character, leading lady rom-com moment.

SHIPKA: Yeah, absolutely! I would almost go as far as to say it's my first rom-com because I did a movie maybe six years ago called Let It Snow...

WEISS: That was sort of ensemble, almost like Love Actually, right?

SHIPKA: Yeah. It was a little Love Actually. It was Christmas. It could technically fall into the rom-com bucket, but as far as a first proper rom-com goes, this is it for me.

WEISS: How do you feel about being a rom-com leading lady? Because I think you're destined to be an iconic one.

SHIPKA: I'm obsessed. I love watching rom-coms. I love being in them. This movie was so special because I love characters that feel three-dimensional and have depth and have life and a film that is of quality and has a message and all these beautiful things, but also this material is so fun to work with, and I love having fun too. If every rom-com experience was like making Sweethearts, I mean, sign me up — one a year, baby, let's go. I'll just keep doing them. I love it. There's so many different variations of rom-com, and this one was really relatable to me because I have a lot of friendships in my life that have similar sort of tones, and there's those questions we always ask ourselves, even if it doesn't feel like this is a person I should date. I have one weird dream about them and then start questioning everything. We've all been there, so this was such a fun niche topic within the broader rom-com space to tackle.

WEISS: Yeah, it's still a rom-com, even though it ends the way that it does. Okay, you're promoting three movies right now. If you had to plan a dinner party with one person from every movie that you're in right now, who would be at that dinner?

SHIPKA: The variations are so endless.

WEISS: I keep thinking of Pam Anderson, Caleb, and the Rock at your house.

SHIPKA: [Laughs] You're right! This is a perfect dinner. I need to see it immediately, and I need to be there, too.

WEISS: We need to have a combined cast party for your three movies. It's Shipka Fall.

SHIPKA: This is why I usually have a holiday party. There's not one this year because of kitchen renovations, but next year, let it be known...

WEISS: Literally, one of the best holiday parties in Los Angeles is the Shipka Holiday Party. People should know.

SHIPKA: We are going to get the Rock and Pam Anderson under the same roof!

WEISS: With Caleb!

This interview has been edited for clarity and length.