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Sean Kaufman discusses 'The Summer I Turned Pretty' season two
Photo: George Chinsee. Suit: Catou. Shirt: Oak + Fort. Shoes: Magnanni.

It’s a sweltering June day in Midtown Manhattan and Sean Kaufman asks for a green tea. Green seems to be a theme for the day: green tea, green suit, and a green photo backdrop on set; it’s an appropriate motif for the cool, calm, and collected actor standing before the camera. Deep inside, though, he’s ecstatic to see his best friends and The Summer I Turned Pretty co-stars at the season two premiere later in the day.

Every now and then, his excitement bubbles to the surface by sneaking in a joke in-between camera angles and humming the tunes of David Bowie. He’s also looking forward to grabbing food at the Japanese market down the street where he used to go to with his mom while growing up in New York City. It’s a full-circle moment when the up-and-coming actor is recognized by a fan outside the grocery store immediately after his shoot and proudly takes a selfie with them. “You know, sometimes I can’t wrap my brain around it,” he says about public recognition and the feverish fanbase following the success of The Summer I Turned Pretty. 

Not a big fan of love triangles, but the fantasy of it is a wonderful thing.

Fame and fanfare are relatively new concepts to Kaufman, who, like most of the cast, are getting used to stardom. Adapted from Jenny Han’s book series of the same name, The Summer I Turned Pretty became one of Prime Video’s most popular series and captured a plethora of fans in 2022. Thousands of theories and fan cams proliferated on social media with the complicated love triangle of Cousin’s Beach between Belly Conklin (Lola Tung) and brothers Conrad (Christopher Briney) and Jeremiah Fisher (Gavin Casalegno). Kaufman plays Belly’s older brother, Steven, and draws from his own experience to help guide—and, true to most sibling dynamics, lovingly tease—his onscreen sis. 

In the opening scenes of season two, Steven gives an ambitious and wise graduation speech as valedictorian in the midst of tragedy. Conrad and Jeremiah’s mother (and Belly and Steven’s mother’s best friend) Susannah has just passed away from cancer, which causes major tension in each character’s relationship throughout the new season. The fresh grad steps up to set the tone for the summer—establishing hope for the unpredictable future. 

Photo: George Chinsee. Suit: Catou. Shirt: Oak + Fort. Shoes: Magnanni.

Though the storyline for this season can be depressing at times—like the Fishers and Conklins facing the threat of losing their childhood beach house and experiencing a ton of heartbreak—Kaufman assures that the cast reveled in fun summer activities when they could. “Even in Jenny’s trailer she would be watching, laughing, and taking notes while we were dancing,” he says about filming an energetic scene with his castmates. His photoshoot with StyleCaster echoed that same atmosphere of unfiltered joy and fun as he posed with a grin for the camera. I caught up with Sean Kaufman to talk about his brotherly love beyond the small screen, his relationship with his fellow cast members, and the immense popularity of the show.

Photo: George Chinsee. Suit: Catou. Shirt: Oak + Fort. Shoes: Magnanni.

In what ways do you relate to Steven and in what ways are you different from him?

Off the bat, the sibling relationship is something I can relate to a lot. When I first got the audition, the first thing I related to was that I have a younger sister by three years. I had that understanding of older brother/younger sister kind of stuff. Every time Steven goes, “Ew,” that somehow really means “I love you” to Belly. It’s something that I know from experience myself. I did it to my sister all the time. Steven has a really big heart for a lot of his friends—Conrad, Belly, and Laurel—which I’d like to think I share with him. Maybe that’s a tad narcissistic. But then we differ in where he cares about stuff. He really loves stuff and really likes nice clothes. He always likes to look a certain way and feel a certain way. He’s very concerned with (and very rightly so) money, college, and these things he puts a lot of his focus into. I think just for myself. I’m like, “I’m cool like the Earth. That’s all I need.”

I’m really glad you mentioned your relationship with your sister. Were there any parallels that you saw in your own personal life experiences as a brother?

She might get mad at me for saying this, but I don’t care. It wasn’t until a couple of years ago that I realized my sister was capable of dating and that she is going to become a grown adult. I think that’s a huge thing for Steven as well. Especially with these two brothers, Conrad and Jeremiah, who he just thought of as his best friends, he didn’t even think about them being in a relationship with Belly at all. Then all of a sudden, one summer, they come in and all eyes are on her, and his best friends are kind of taken away. I’m like, “Oh my God, wait, my actual sister is not a little 12-year-old. She’s a growing adult who can make decisions and has personal life?” It’s a very funny realization for any older sibling to go through.

How did you deal with all of the emotions Steven has at the beginning of season two? 

It was a little hard because I think all the characters are dealing with grief immediately. It was tough to figure out for Steven. He says in the show that he feels like an asshole—where he’s very excited for the bright future that he has. He’s going off to Princeton and things are looking up for him but he struggles to allow himself to feel good sometimes, because of this heavy emotional toll and seeing it, especially on Belly. Seeing how affected by it she is, and him being like, “Am I an asshole for wanting more in life and not just wallow all day?” It was tough. It was just a lot of script work that went into it. A lot of my scenes with Conrad were really lovely and emotional. Chris and I lived together for season two, and we just spent every night after shooting eating together and then we would sit on our porch and just run those scenes just over and over until they were second nature. Just like a level of work.

Photo: George Chinsee. Suit: Catou. Shirt: Oak + Fort. Shoes: Magnanni.

During these episodes, there are definitely undertones of grief. But, there’s also a sense of urgency where the characters want everything to be OK when saving the house while also having fun at the same time. How did you all balance those feelings? 

It was so funny because we’re a cast that likes to laugh, joke, and break attention always. I remember shooting the funeral when all of us are really taking the time to get in that space and prep before. Jackie, Lola, Colin, and all these people are just sitting, meditating, and you see some tears flowing. Then half the time I would just try to crack a joke, and it would just not land and it would just be silent. I had to be like, “Oh yeah, you guys are in the middle of crying right now. I’m sorry.”

But then it would also be balanced by the carnival days. Oh my God, I will never, ever, ever forget the laser tag scene. Our wonderful director, Isabel Sandoval, actually let us do a whole complete round of laser tag. They just said, “There will be cameras somewhere. Don’t even worry about the plot, just play.” It was those situations and days where it all just flowed back—like the ease and the forgetting everything else, but just being in that moment and having fun. Everything else kind of faded away. It was weird doing that on Monday and then having a funeral on Tuesday. 

Even with that laser tag scene, I can see that your relationship with the cast is phenomenal. What’s that relationship like beyond filming scenes together? 

They’re my best friends. It’s not even in a cliché way. I see them every day. Chris and I play video games every day. Whenever somebody’s in the city, we’re just constantly hanging out and doing shenanigans together. To the point where when I was first doing interviews, I was transitioning slowly from saying the word “castmates” or “co-stars” to “my friends.” It was a really lovely realization. I feel so lucky and so blessed to have them in my life.

The popularity of the show completely boomed last year. Before the show started, would you have imagined yourself here where you are right now? 

No, I don’t think we imagined it. I don’t think we really tried to. I know the vibe on season one was that we were just going to do the best job possible. We were going to have the most fun doing it. When it finished, we were not ready to send off or to say goodbye to these characters, but we did what we could. And we all felt really happy and overjoyed by that. 

Every time Steven goes, ‘Ew,’ that somehow really means ‘I love you’ to Belly.

When the news came that season two was coming back, we were just hyped and excited that we get to run it back! We get another chance to just be with the best people and just do the best thing. For a lot of us, this was our first thing so we really had no idea what it was like to shoot. I think one of the things that was always really funny to me was when we filmed season one, a lot of the crew would tell us every day, “This is a special project. You guys have a special bond, it’s a special thing.” We thought they were just buttering us up like as an ally just to make us feel better. So we were like, “Yeah sure, whatever.” Then, the huge reception came back from many, many wonderful fans. When we went back to shoot for season two, the crew was just like “Yeah, we told you so.” We were like, “Oh yeah, you know, you’re right.”

Because this is your first big thing, do you have any fun fan interactions that you’ve experienced in the past year?

There are so many. It’s really awesome to see how much we’ve affected people. One of the craziest things ever is when my girlfriend participated in this traditional Bulgarian dance troupe, and they had the honor of performing in Chicago for this giant Bulgarian festival. I went with her and tried to be a supportive boyfriend. I remember there were so many young people there that recognized me. Some of them barely spoke English. A lot of them were from Bulgaria and they would come up to me and express that they watched the show and loved it. It meant so much to us. That was when I realized that it reaches so many more communities than what I could think of. To think that something like this has that power is a crazy, insane thought process.

Photo: George Chinsee. Suit: Catou. Shirt: Oak + Fort. Shoes: Magnanni.

How do you want Steven and Taylor’s upcoming relationship to evolve, and how will you explore it as an actor?

Hopefully, we get the chance to. I’m excited to see how it goes. I think season one was very much about Cousin’s Beach, and this is what’s going on. Season two is the start of the world opening up. It’s really beautiful to me to think about, like a tree growing, and every single branch kind of roots off in different directions. It’s still the same tree, but these branches go in separate directions. I’m like, “OK, well now Steven is going to college, Connie and Jer are going to college. The characters could go to the real world and do whatever. There are so many possibilities for the story to branch out to that I’m just excited to get the chance with Rain to explore that, especially being a little bit older and closer to our actual age. I can’t express how amazing Rain is, so to get the chance to work with her again is *chef’s kiss*

What advice would you give to someone who has a sister who is in a love triangle with their best friends?

This may be unpopular, and people might not like to hear this, but if my sister were in a love triangle with two brothers, I’d tell her to figure that shit out. I think something that is really hard to see in love triangles is that all they do is inherently end up hurting each other. They never mean to want to hurt one another. But throughout both seasons, they just do. To think that if it was my sister, I’d tell her “Hey, like, you gotta make a choice. I know it’s hard and it’s tough. But the more you prolong this, the longer this keeps going, the more you’re just going to hurt the people that you love. That’s not good for anybody.” So not a big fan of love triangles, but the fantasy of it is a wonderful thing.

The Summer I Turned Pretty is available to stream on Prime Video, with new episodes dropping each Friday.


Photographer: George Chinsee
Stylist: Alison Hernon
Grooming: Laila Hayani

This interview and photoshoot were conducted before the SAG-AFTRA strike.

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