By Samantha Highfill
March 30, 2018 at 09:30 AM EDT

A version of this story appears in the latest issue of Entertainment Weekly, on newsstands now. Buy it here or subscribe for more exclusive interviews and photos, only in EW.

Gilmore Girls fans know the scene: Rory drops her books in the hallway at school, and when she looks up, there’s a cute boy standing next to her. From the moment he gets her Rosemary’s Baby reference, it’s clear that he’s more than just a pretty face. His name is Dean Forester, and he’ll become Rory’s first love. But before Jared Padalecki stood in that hallway in Dean’s leather jacket in 2000, Nathan Wetherington did it — in Dean’s cargo jacket — for what’s become known as the “unaired Gilmore Girls pilot.” “Gilmore Girls was my first experience on set, ever, professionally,” Wetherington tells EW. “We shot that scene, like, 45 times so they could get the books to fall the right way. It took all day.”

Wetherington, who was in his early 20s at the time, doesn’t remember much about his brief experience filming the pilot in Canada, aside from the fact that Sean Connery was staying in his hotel. And then there was the hair. “I kind of let myself get hustled. I remember going into makeup for the first time and they sprayed my hair over and they were combing it down and I didn’t know if I could say anything,” Wetherington says. “I was like, ‘This doesn’t look like me, I don’t know what’s going on right now.’ I remember feeling very uncomfortable in my own skin.”

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And that uncomfortable feeling wasn’t helped by an incident that nearly stopped production on the entire pilot. “I was brushed by the knuckle of a focus puller who was taking a measurement and I couldn’t have cared less. It almost shut down the set,” Wetherington says. “I remember that getting the set pretty tense, especially with the camera department. I immediately felt horrible about the whole situation. He barely touched my cheek. It was such a minimal thing but that kind of set the day off. That’s the only scene I remember.”

To be fair, Wetherington’s spotty memory has a lot to do with another role he was up for at the time, this one taking place in a galaxy far, far away from Stars Hollow. “I was actually at Skywalker Ranch, having just walked out of a meeting with George Lucas for Anakin, when I got a call that I had booked Gilmore Girls,” Wetherington says. “I think the only reason I got cast in Gilmore Girls was because word was traveling that I was in the running for Anakin.”

Ultimately, an overwhelmed Wetherington took himself out of the Anakin race before it was cast (the role went to Hayden Christensen), a move he regretted: “I wrote George a letter after it had been cast and was like, ‘I really feel like this should’ve been me. I think I made a mistake.'” As for Gilmore, that experience also ended with a letter … or two: After shooting the pilot, Wetherington received a letter telling him the show had been picked up, followed by a second one telling him the role of Dean was being recast.

But those whirlwind couple of months wouldn’t be the only time the young actor almost landed a life-changing role. “I tested for The O.C. years later for Seth,” Wetherington reveals. “I tested with Ben McKenzie. It was myself and Adam Brody.” Ultimately, of course, the role went to Brody. As for Wetherington, he eventually grew tired and left the business to try his hand at Corporate America for a few years. But he didn’t stay away for long.

He might not have been Dean or Anakin or Seth, but he’s still trying to make a name for himself. Currently, he’s finishing up his directorial debut, a film titled A Thousand Miles Behind, which he also wrote. This time, he’s making sure the word “almost” isn’t a possibility.