July 14, 2016 07:00 PM

It’s never easy being a teenager, but when your best friend starts hooking up with your archenemy of an older brother, high school can become unbearable.

That’s where Hailee Steinfeld finds herself in the new coming-of-age film The Edge of Seventeen, and PEOPLE has an exclusive first look at its trailer.

The actress-singer, 19, stars as high school junior Nadine, who is at peak teen awkwardness when she catches her golden child brother, Darian (played by Blake Jenner), in bed with her best friend (played by Haley Lu Richardson).

Hailee Steinfeld in Edge of Seventeen
Murray Close/STX Productions

But just when Nadine thinks she can’t feel any more alone, an unexpected friendship with an empathic classmate (played by Hayden Szeto) gives her a much-needed confidence boost. The film also stars Kyra Sedgwick as her good-intentioned but ultimately inept mother, and Woody Harrelson, as her history teacher and reluctant confidante.

“I remember reading the script and feeling like I’ve never connected with a contemporary piece the way I connected with this one before,” Steinfeld tells PEOPLE of the new role.

Steinfeld, who snagged an Oscar nomination at the age of 14 for True Grit, did not exactly have the typical high school experience, but that doesn’t mean she can’t relate to those awkward teen years.

Edge of Seventeen
Murray Close/STX Productions

“I think some people tend to forget that just because I didn’t necessarily go to a high school, I didn’t live any of those experiences, but I did,” she says. “I’ve experienced so much of what she has gone through in my life – just in a different way.” Working on a new movie set, she says as an example, can be a lot like the first day of school.

Hailee Steinfeld and Woody Harrelson in Edge of Seventeen
Murray Close/STX Productions

In an effort to make the film as authentic as possible, screenwriter and first-time director Kelly Fremon Craig interviewed teenagers across the country to learn more about modern high school life.

“That research was just incredible,” Craig tells PEOPLE. “I talked to a ton of teenagers for hours and the interviews started turning into therapy sessions. All of a sudden you get incredible details that are painful and funny and beautiful and weird. Things you can’t possibly makeup.”

For more on Steinfeld and The Edge of Seventeen, pick up the new issue of PEOPLE, on newsstands Friday

People Magazine Cover

Having an actress as talented as Steinfeld also went a long way toward giving the film the realness Craig was looking for. “She’s an amazing human being and an amazing talent,” the director says. “She can make you laugh and then break your heart the next second. It was one of those things where nobody could do it but her.”

And the admiration is mutual. “Working with Kelly was amazing,” Steinfeld says. “The script is very, very close to her heart, and I connected with it on a very high level, so her and I were really on the same page since day one.”

Steinfeld also raved about her time with Harrelson. “We just couldn’t keep it together,” she says, laughing. “I really hope there’s some kind of blooper reel.”

The Edge of Seventeen arrives in theaters on Sept. 30.

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