Chris Pine’s directorial debut, Poolman, is almost here, and earlier this week the Hollywood star strutted the red carpet in a viral ensemble only he could pull off that had him in a blazer with shorts and hiking boots. While at the premiere for his upcoming movie, Pine was asked to reflect on his first big red carpet, which happened to be for Princess Diaries 2: The Royal Engagement, and it turns out he wasn’t always this effortless at events.

While on the red carpet for Poolman, which is coming up among 2024 movie releases this May, Chris Pine thought back to his first premiere, which was circa 2004, with ET. In his words:

The premiere for that was at Disneyland. I got picked up in a stretch limo with my agent. We went there and I was so nervous.

Talk about an iconic first red carpet-premiere, eh? Chris Pine was 23 years old when he made his feature film debut in the Princess Diaries sequel, and it was alongside Anne Hathaway and Julie Andrews. When speaking about his first premiere further, he recalled his outfit at the time:

I remember wearing converse, and like, gray pants and just being absolutely terrified, just because this whole experience, people shouting and doing the whole thing is like you gotta get used to that whole thing.

Princess Diaries 2 was Chris Pine’s introduction to being a Hollywood lead, and he recalls the red carpet experience getting him super nervous. When CinemaBlend spoke to Pine about his first movie back in November, the actor recalled being on the set of Princess Diaries 2 as well. As he shared, he was “so terrified basically the whole time” that he was going to “screw up.” He also described being on the set of the Disney movie as a “PhD fast course in how to be an actor.”

If you can believe it, Princess Diaries 2: The Royal Engagement turns 20 years old this August, making it the perfect time to rewatch it. You can check out our thoughts on the Disney sequel after we rewatched it and stream the comedy with a Disney+ subscription. Word on the street is that another Princess Diaries movie is in the works, with Hathaway recently telling V Magazine that development on another installment is “in a good place.” We’ll of course have to see if Pine does get a chance to return as Mia Thermopolis’ man.

As Chris Pine paid homage to his first premiere 20 years later, he celebrated a milestone having directed his first feature film with Poolman. It’s about a pool cleaner living in Los Angeles who uncovers a water heist, i.e. Chinatown. The movie initially premiered at the Toronto International Film Festival last year and is set to hit theaters on May 10.