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Celebrating the Lost Gilmore Girls Spin-Off With Alix Kermes
The actress who played Lily in Windward Circle joins us for an illuminating chat
We all wonder at some point how our lives might have been different had one thing happened or not. It’s the “sliding doors” or “butterfly effect” phenomenon: if one event happened, how would that one event have changed everything? All Gilmore Girls fans know about the spin-off series that never was: Windward Circle. In Season 3, Episode 21: “Here Comes the Son,” Milo Ventimiglia’s Jess leaves Stars Hollow to go out to Venice, CA to find his father. During this “backdoor pilot” episode, fans were introduced to new characters: we had already met Jess’ father, played by Rob Estes, but we also met Sasha played by Sherilyn Fenn and her daughter Lily, played by a young Alix Kermes.
During June 2022, we threw a month-long Gilmore Girls extravaganza at Remarkist with a Super Sensational Summer Spectacular, and we took the opportunity to speak with lots of former cast members who had anything to do with the beloved TV show. During a watch party of “Here Comes the Son” we invited actress Alix Kermes, who at the time of filming was just nine years old! Our conversation with her was so much fun and informative, and at the end all attendees were downright sad 😢 that Windward Circle never took off.
Alix, like many actors and former cast members of Gilmore Girls, had never watched the series all the way through. She had of course watched this episode as it was one of her big breaks as an actor, but other than that she confessed she’d only seen a handful of episodes.
Getting a role on Gilmore Girls
Based in Minnesota as a child, Alix got into acting when she was five and continued through the age of fifteen. At that point, she took time away from the profession. “I had a talk with my parents. I was really focused on school at the time and I wanted to basically be a kid. My parents were always really good about balancing it, but there came a time in high school and middle school where kids can be mean if you have that weird hobby.” She would fly ✈️ to Los Angeles for “pilot season” in the spring, leaving school for a month, and then fly back to CA for auditions. Her mother would take her back to L.A. for three months every summer. They were checked into her flight back home to Minnesota when she got the callback for the Gilmore Girls/Windward Circle audition. She recalls that she and her mother briefly considered getting on the plane anyway, because it was her sister’s sixth bday party! 🎂 But they stayed, her dad handled the party, and Alix pursued the opportunity of a lifetime.
Alix remembered that she did five (!!) rounds of auditions which seems crazy for what Gilmore fans consider a small role of Lily, but because it was a backdoor pilot show, the casting was a very big deal. She explained, “In this episode, they were just introducing our characters…Back in 2003 I signed ✍️ my contract for six or seven years. My very next episode, Lily was going to have a huge long monologue and discussion with Milo…so she had this whole character development that was going to be happening. They had to make sure that they found someone not only just for this quick little appearance here, but someone who could do monologues 🗣 moving forward. And so it was five rounds of auditions; I was nine and the final round of auditions was down to myself and one other little girl. I walked into the room and there were thirty-something adults sitting there.”
Windward Circle: the spin-off that never was
The reason there were so many people in the room was because this wasn’t just a cast audition for a small role: Windward Circle was slated to be a huge new TV show on the WB network, with lots of support behind it. The casting of the character of Lily was crucial.
“The final [audition] was at the Warner Brothers Ranch which was where they brought in everyone…because it was down for the next lineup of shows. Back then you didn’t have all the streaming platforms so not everyone could get their show out there; you had to fight for the slots. It came down to One Tree Hill and us that were bidding for the final time slot. 😬 If a different show didn’t get renewed or whatever, it was us or One Tree Hill. Well, we all know what happened; One Tree Hill got that time slot. But they had signed us for seven years.”
Attendees at the event grappled with this and a hush came over the room: the idea that a young actress was signed to a seven-year contract for a show with a huge amount of promise, only to lose the opportunity to a time slot that another show everyone in the room also loves was really hard to hear! Not much is known about Windward Circle, and other stories about why it never took off reference budget concerns. We might never know the full reason, but this revelation from someone who was deeply affected by the cancellation was mind-boggling.
Alix continued: “It was a huge publicity thing…Gilmore Girls was launching this new series spin-off and they were tying us into Gilmore Girls. They were going to have us mingling in throughout the episodes here and there. But it was BIG publicity. It was a spin-off with Milo; Jess was getting his own show. We knew it was Gilmore Girls, but at the time I was nine; I didn’t really understand, I wasn’t watching it, and my parents weren't big on it either. I knew it was big at the time but my nine-year-old self didn’t grasp it.”
Alix was awarded the part out of hundreds of young hopefuls, and it certainly felt like her entire life was about to change. “I got the part, I flew home to Minnesota, I came back out and shot the episode, I flew home, we were invited to the wrap party, all of that.” In March she was cast, in April they shot the episode. In the meantime, her family started making plans to relocate her and her mother to Los Angeles for filming, and making all the necessary arrangements.
“There was a period of time where we were looking at apartments…my mom and I were going to be moving out there. We were talking with schools 🏫 and looking into the studio schools. As a child actor, back then, it was three hours a day. If I was on set I had to have time in my trailer where my studio teacher would come and my school would send over the homework I was missing out on and I would complete the homework with her in my trailer for three hours.”
But all of this planning was cut short very soon. During “upfronts” season, which is where networks showcase their seasonal TV lineups to advertisers, everything changed. “May was the upfront and shortly after that timeframe was when we found out that it wasn’t going to go.”
Revisiting the episode
Alix hadn’t watched the episode in years, and her excitement to watch it again was palpable. She had so much exciting information and anecdotes to share, including memories about the set, attention she got from everyone, and hanging with Milo. Her stories were front of mind thanks to the handy scrapbook 📸 that she made during her time filming! (You can catch a glimpse of her incredible scrapbook on her Instagram!)
The father/son dynamic
Alix talked about how Windward Circle was going to highlight the father/son relationship between Jess and his dad, which has an opposite characterization to the mother/daughter relationship of Rory and Lorelai. In Gilmore Girls, the hallmark of the show “is the closeness of the mother daughter dynamic and how they know every in and out of each other, but with Windward Circle it was going to be Jess who is virtually a stranger to his dad and how they have to learn about each other so it was going to be a completely different twist on a father/son versus the mother/daughter.”
Working with Milo Ventimiglia
Lily and Jess “were going to have a really cool close knit brother/sister-ish relationship,” Alix said. “They were going to be extremely close but of course we never got to show it.” Of costar Milo, she said he paid a lot of attention to her and was really nice to work with. “He would come up and hug me and we would just hang out on set.” 🤗
The show, Alix explains, “was going to be Amy’s [Sherman-Palladino] new baby where she was going to put all of her energy and all of her effort. This was going to be her new big project. The amount of backstory that was there, and thought…they were trying to set it up for as much success as possible.” Alix had been given the second episode’s script 📒 and remembers reading it. “Lily had huge monologues of dialogue [with Milo’s character] about Abraham Lincoln. I don’t remember the synopsis. This was back in 2003.” She revealed that the writers had written six episodes for the show that never ended up getting filmed.
When asked how similar Alix was to Lily, she said, “I was very similar in certain ways and then completely different. I wasn’t quite as eclectic as her but I did have glasses 👓 and ironically they called my mom and had gotten in contact with my true eye doctor and they sent over the real prescription for my glasses at the time and they had replicated my prescription in a pair of their set glasses.” She went on to say that her right eye’s eyesight is much worse than her left, and her glasses had a much more magnified prescription on the right side. So wearing glasses, her right eye was more magnified on film than her left, which looked tiny by comparison! So she ended up wearing costume glasses.
And what about that wardrobe she’s seen hiding in? “They did have that wardrobe custom built to my measurements. They had to have me sit down in a crouched position; they had to have my mom measure how big I was from the butt to the top of my head when I was sitting, how far out my legs would go comfortably because they didn’t want to cram me into that little wardrobe.”
“My character in the original breakdown was described as…they wanted her to look like an owl, a true bookworm.” 🦉 Cue the “aw!” They certainly got it right. When Milo, as Jess, opens that wardrobe and Lily is hiding inside, that’s exactly how Alix looks in the scene. Alix explained that Lily “was always going to be hiding somewhere with a book 📚 and that was going to be one of her favorite spots so they custom built it.” Sound a little familiar? Maybe a little bit like Rory….or April?
The star treatment
On the set, “I was treated like a little bitty rockstar. It was the coolest experience,” Alix said. “Being on set it was…I don’t even know…it was like, ‘Alix is traveling, Alix is traveling!’ and boom everyone was moving making way and cars were going and things were happening and it was just like an entourage. It was the weirdest, coolest experience I’ve probably ever had.” She recalled this experience with so much excitement and gratitude.
“I remember vividly even back to my very first audition, in the casting room…at one point they literally were chanting ‘We love Alix! We love Alix!’…from then on it was the red carpet treatment, because they were planning on having this child grow up on this set.” The cast and crew knew in the back of their minds that this was the start of a nine-year old girl’s career trajectory over the course of the next seven years; they planned to watch her transform over the course of the show.
“My agents sent me star lilies. They sent a huge bouquet 💐 of star lilies for their new “star” “Lily”…it was a whole production.” But she’s not at all regretful about what happened. “It’s opened so many doors 🚪 and I just cherish all of it. It’s a really cool experience to look back on; not a lot of kids get to see it.”
What if Windward Circle had made it to air?
Here’s a thought experiment: what might have happened if the show had aired and been successful? Gilmore Girls would have had a larger fictional universe with a spin-off show, and the existence of Windward Circle might have changed some Gilmore storylines. Sherilyn Fenn wouldn’t have been on Gilmore Girls as April’s mother; April also might have been a different character, or not existed altogether, because Lily’s bookworm 🐛 status is so similar to the April character. The alternate universe that might have been is mind-boggling!
There also might not have been a One Tree Hill! Can you imagine? Chad Michael Murray (or Gavin DeGraw!) wouldn’t have had his big break; instead, maybe this would have been Milo’s big break (also: imagine a world where Milo Ventimiglia didn’t go on to star in Heroes or This Is Us? His career trajectory might have been entirely different.)
We loved hearing from Alix Kermes about everything she’s been up to since that glimpse we had of her in her custom-built wardrobe, looking cute as a bookworm. In 2021, she starred in Baking Up Love, a romcom about a small town bakeoff. And just a glimpse at her IMDB page shows a slew of projects coming up for her that we can’t wait to watch!
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