How Sophia Lillis and Wyatt Oleff’s IRL Friendship Inspired the Core Relationship of ‘I Am Not Okay With This’

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I Am Not Okay With This

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When you’re talking about Netflix’s new series I Am Not Okay With This, IT is bound to come up.
That’s because IT and IT: Chapter Two stars Sophia Lillis and Wyatt Oleff are reunited in I Am Not Okay With This as awkward friends Sydney Novak and Stanley Barber. Syd is a grieving teenager struggling with her ambivalent feelings towards her own innate superpowers. Stanley, on the other hand, is an all-too normal boy who is crazy cool because he’s not cool. Together, the two make a perfect odd couple and their chemistry zings through the series’ first season.
During a visit to the show’s Pittsburgh-based set, Decider got to chat with the cast and creative team behind I Am Not Okay With This. According to Lillas, Sydney has a lot in common with the Molly Ringwald characters of the Brat Pack era, while Oleff shared that Stanley is loosely based on Pretty in Pink‘s Duckie. As it turns out, Lillis and Wyatt were cast not because of their resemblance to John Hughes’s characters or their work in IT, but thanks to their real life friendship.

“They don’t have to hide themselves…and I feel like that’s kind of the same with me and Wyatt. I get to really be myself with him.”


One of the show’s executive producers, Dan Levine, explained the casting process to Decider and about a dozen other journalists during the set visit. “It was a really interesting process. It took us a very, very long time, and a little bit of panic towards the end where we just didn’t find that right person [for Sydney]. When we found Sophia, we just knew it. She just had that deadpan quality, she was really likable, and really vulnerable, and you really feel for her,” Levine said.

“And then the Stanley search was even harder. We didn’t know what to do. And then someone had the brilliant idea — they saw that [Sophia and Wyatt] were actual friends in real life. There’s a lot of stuff on social media with those two palling around and it was just a brilliant lightning stroke. We were like, ‘Oh my god, this is our Stanley.'”

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Wyatt Oleff’s recollection of the events that led him to be cast are a little bit different. He told a roundtable of reporters, “For this role, I was lucky enough to get an audition for it. And then I saw Sophia was in it, and we were like, ‘Oh, okay, well this is important,’ so we prepared a lot. I went into the audition and I had a great time…and we were able to get extra behind-the-scenes info on where I was at in terms of getting the role. Finally, yeah, I got the role.”
Levine said, “Thank God we did that because the chemistry they have — and even watching those two between takes — they’re so funny and goofy. It’s like a brother/sister vibe. They bring out great qualities in each other.”

“In real life, it’s my duty to annoy her, and Stan does it [to Sydney] anyway.”


Oleff explained that he and Lillis didn’t actually become close on the set of IT: Chapter One, but rather over the time they spent together afterwards.

“Obviously were were all really good friends on IT 1, but I didn’t get the full experience of just interacting with Sophia very often. So when we started doing more press for it, then there was a time when it was just her and I, and our parents, and we’d go somewhere and we’d hang out and stuff. We would just have those little moments where we would build our friendship,” Oleff said.


Lillis burst into a giddy smile when Decider asked her about working with Oleff on I Am Not Okay With This. “I am so happy he is apart of this as well,” she said. “I’m really happy I know him, so I don’t really have to pretend to be friends with him. I’m already friends with him. It’s always fun to get to know people. It’s also really nice to have someone and you know that person already.”

Lillis went on to explain that Sydney and Stanley “get very close” over the course of the first season of I Am Not Okay With This. “They’re very good friends and kind of the way they talk to each other, they don’t have to hide themselves. What you see in Sydney is she’s still trying to accept every part of herself, but being with him, she can really feel like herself, and I feel like that’s kind of the same with me and Wyatt. I get to really be myself with him. And I think it’s the same vice versa,” Lillis said.
Oleff’s interpretation of their characters’ bond was a little more mischievous. “In real life, it’s my duty to annoy her, and Stan does it [to Sydney] anyway,” Oleff said. “He doesn’t mean to, but he does it. It’s not on purpose or anything. After a bit, she’s like, ‘UGH,’ but in the best way possible. She still views him as a nice friend, but just some stuff he does, just some little quirks he has, just make her a little annoyed.”
I Am Not Okay With This premieres on February 26, 2020 on Netflix . 

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