By Shirley Li
February 13, 2019 at 03:30 PM EST
Credit: Everett Collection

Every day until Valentine’s Day, Entertainment Weekly is celebrating our special romantic-comedy-themed Untold Stories issue. Check out all of our behind-the-scenes tidbits, reunions, and oral histories — and follow #LoveEWstyle on Twitter and Instagram.

Cameron Crowe’s directorial debut turns 30 this year, and we just can’t be chill about the film — even though we know we must. Crowe and star Ione Skye — who played Diane Court, the brainy, pen-wielding love of John Cusack’s Lloyd Dobler — share some tales from the making of the teen romance.

Skye — at 17, the youngest in the lead cast — was fearful of letting everyone down.

“I was really intimidated,” she says. “I remember feeling, ‘Oh no, I’ve got these big scenes coming up. I hope I’m good.'” Her nerves ended up working in her favor, Crowe says. “She wasn’t written to be quite as fragile, but seeing Ione play it that way was really tender. [Her performance] made me feel like Lloyd understanding her better than anybody else would be really powerful.”

John Mahoney had plenty of competition for his role.

Crowe remembers some boldfaced names coming in to read for Jim Court, Diane’s father: Danny DeVito, Randy Quaid, Dick Van Dyke, Jeff Goldblum, and Richard Dreyfuss were all considered — but only Dreyfuss felt he was up for the wrong part. “He said, ‘I want to play Lloyd,'” Crowe recalls. Hey, if Crowe hadn’t been able to convince Cusack to do it…

Skye and John Cusack dated years after filming — sort of.

Both were in relationships while working together, but they reconnected down the line and, well… “We ended up having a couple dates over the course of a few years,” says Skye. “Here and there, we would meet up and fool around a little.” The pair eventually fell out of touch, but Skye says they’ll always share “a fondness” for each other as friends.

Filming the boom-box scene was a lot less romantic than you think.

“In my mind, I was like, ‘I hope my stomach isn’t looking fat in this nightgown,'” Skye recalls. “I was a real teen.” Besides, she never heard Peter Gabriel’s heartfelt, iconic track “In Your Eyes” while filming — or even saw Cusack. The two shot the sequence separately; in fact, Cusack held up the boom box in the middle of a park in North Hollywood, across from a 7-Eleven.

Speaking of the boom box, “In Your Eyes” almost played a third time in the film.

Editor Richard Marks fought hard to incorporate the song into the ding-lightful ending, but Crowe pushed back. “There was a big debate,” Crowe remembers. “I was so adamant [in saying], ‘Let’s not go back to the well.'” When he revisited the film recently, though, Crowe saw things differently. “I was like, ‘Richie was right,’” he says. “If push came to shove, I would not use it again, [but] it was funny to think I could have.” Because in the end, the film’s perfect as is.

—Additional reporting by Ruth Kinane.

For more Untold Stories from your favorite rom-coms, pick up the new double issue of Entertainment Weekly on stands now, or buy it here. Don’t forget to subscribe to EW for more exclusive interviews and photos — and follow #LoveEWstyle on Twitter and Instagram.

Related links: