Source: Entertainment Weekly

After moving to Hollywood in her early teens, the future Clueless star was in a pattern of almosts.

“At first, I was auditioning almost every day, but I wasn’t getting anything,” Silverstone tells Entertainment Weekly. “Then, all of a sudden, I started to get close to everything. They would say, ‘It’s between you and one other girl.’ But that actually was worse. I’d get so close and then be disappointed, where before I didn’t care.”

And initially, that was her experience with The Crush, writer-director Alan Shapiro’s film about a 28-year-old writer who finds himself the object of a 14-year-old girl’s dangerous obsession.

“They had me back many, many times, and it seemed like I was going to get the part — and then they offered it to someone else. It felt really bad. For some reason, I felt like I was supposed to play this psychotic character,” she recalls with a laugh.

But then, Silverstone says, the original star dropped out, she got the call that the part was finally hers.

“I just remember that, when I was little, telling people that I was ‘going to kiss the boy from The Princess Bride, but he’s a lot older than me,'” Silverstone says of starring opposite Cary Elwes, who is almost 14 years her senior. “We had this kiss in the film and, because I was young, I thought that that meant he was my boyfriend now. Not really, but little bit. I went to his trailer and asked him if that was okay, and he was so kind.”

“Lisa Marie [Kubikoff], his wife, sent me pictures from back in the day where we’re laying together, and I’m looking at her while she’s taking the picture like, ‘This is my man,'” Silverstone — who recently graced the cover of EW’s ’90s Issue — continues. “But, really, he was a really good big brother to me and took care. He was so lovely. We had a very professional relationship and he was very big-brother-like to me, and very sweet and kind. It was just a great job. What a great part to play. It was so fun.”

Silverstone shared the Elwes anecdote as part of a larger cruise down Memory Lane, looking back at her iconic ’90s roles, including The Wonder Years, Batman & Robin, Blast from the Past, and more. You can also watch the video interview in full above.

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