Julia Stiles in 1999; Natalie Portman in 1994.Photo:David Keeler/Getty ; Ken Weingart/Michael Ochs Archives/Getty

Julia Stiles At The Premiere Of The Television Movie, The 60s,On NBC. Natalie Portman poses for a portrait in 1994 in New York City, New York. .

David Keeler/Getty ; Ken Weingart/Michael Ochs Archives/Getty

Julia Stilescrossed paths with many other famous actresses in the ’90s, but one encounter still stands out to her.

“I do remember seeingNatalie Portmanand being really starstruck and thinking, ‘Oh, I’m never going to get this job,' " theWish You Were Heredirector told PEOPLE during an episode of thePEOPLE in the ‘90spodcastin 2021. “She was way famous already.”

At the time, Stiles, now 43, was a teenage actress auditioning for roles in New York City. The 18-year-old was living with her parents in 1999, the same year she appeared on the cover of Teen PEOPLE as one of the ‘21 Hottest Stars Under 21.’ She was named alongside other ’90s icons likeJustin Timberlake,Joshua JacksonandKatie Holmes.

Julia Stiles in 2025; Natalie Portman in 2024.Jamie McCarthy/Getty; Maya Dehlin Spach/WireImage

Julia Stiles attends a screening of “Wish You Were Here” at the Crosby Street Hotel on January 15, 2025 in New York City. Natalie Portman attends Apple TV+’s “Lady In The Lake” photocall at SAG-AFTRA on December 02, 2024 in Los Angeles, California.

Jamie McCarthy/Getty; Maya Dehlin Spach/WireImage

“I was auditioning in New York, which is kind of a smaller group,” theJason Bourneactress said. “LeAnn Rimes,Josh HartnettandMichelle Williams, they were probably all in L.A.,” she added of some of the other stars on the Teen PEOPLE list with her.

But Stiles rubbed elbows with her fair share of future megastars on the East Coast, too.

“My last year of high school, I switched to a performing arts school andChristina Ricciwas there,” Stiles recalled.

The budding actress’ circle of famous friends grew as she continued to work and book roles.

Julia Stiles in 1999.David Keeler/Getty

Julia Stiles At The Premiere Of The Television Movie, The 60s, On Nbc.

David Keeler/Getty

“Once you actually have the job and you’re on location, not only are you sort of forced to hang out with everybody and you quickly become friends, but you have the confidence of, I’ve already got the job,” she says. “People that you would see every day, we’d become more friendly with.”

In more recent years, the mother of three has taken a step back from acting but still appears in projects from time to time. In 2024, she starred alongsideHeather GrahaminChosen Family. This year, she is making a foray into directing.

PEOPLE recently caught up with the star at the premiere of her directorial debut,Wish You Were Here,on Jan. 15 in New York City, whereshe reflected on her character Kat Stratfordin10 Things I Hate About You, therole she gets “recognized” for most.

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“And then I read10 Things I Hate About Youand Kat Stratford was like this feisty outspoken girl who did not care what people thought about her,” Stiles continued of the character, who played opposite the lateHeath Ledger’s Patrick Verona.

“So it meant a lot to me to be in that movie,” she said, “and that it resonates with people still is so great.”

source: people.com