When you think of a “tourist spot,” Connecticut probably isn’t the first place that comes to mind. Maybe you think of Italy, Greece, New York, or Cancún.
What I’ve recently learned, however, is that for a small, fiercely devoted demographic, Guilford, Connecticut is an annual must-visit. Each fall, as the leaves begin to change and the air grows brisk, they make the trip for a festival celebrating their favorite fictional town.
This demographic, if you haven’t already guessed, is the Gilmore Girls fandom. The Firelight Fan Festival, hosted by the Fan Fest Society, ran from Thursday, Oct. 15, through Sunday, Oct. 18. Attendees spent the weekend immersed in the fan community, meeting cast members, participating in Gilmore Girls Trivia, and enjoying Guilford’s small town charm.
As I spoke with visitors, I felt less like a reporter and more like a fellow fan. Some told me that they’d seen the show ten, twenty, even hundreds of times. I can’t quite compete with that, but I’d still say Gilmore Girls basically raised me.
Growing up in a small Connecticut town with a single mom, the comparisons to Rory Gilmore began in high school and never stopped. The fact that I have brown hair and blue eyes didn’t help. Neither did my decision to attend Yale with plans to pursue journalism. I wish I could say it was a total coincidence, but I guess I also took a bit of inspiration from Rory. I mean, which ambitious high school girl hasn’t watched those social media videos promising to teach her how to “study like Rory Gilmore”?
It’s safe to say that the show means a lot to me, something the visitors of the festival clearly understood. But beyond the heartwarming, perhaps slightly sentimental connection I have with Gilmore Girls, I also have some deeply held (and slightly controversial) opinions about its characters. This, in my eyes, is the marker of a true fan.
Every Gilmore Girls fan eventually encounters the show’s most timeless debates: Team Jess, Dean, or Logan? Team Luke or Christopher? Is Rory Gilmore’s arc realistic?
As I stood in front of the massive line of fans waiting to meet Scott Cohen (AKA Max Medina), I began to wonder:
Could there be a better place to settle these contentious debates?
Team Jess, Dean, or Logan?
Arguably the most heated debate within the Gilmore Girls fandom: which of Rory’s boyfriends is actually the best match for her?
Among those I interviewed, Team Jess appeared to have the upper hand (85 percent). One woman, Kelly Dougherty, grew up watching the show with her mom and admitted that she has probably rewatched it “about one hundred times.” Her allegiance, however, has changed over the years.
“Growing up, I couldn’t stand Jess. He was mean to her, and I don’t like the bad boy persona,” she said. “But as an adult now, after seeing how he evolved and matured, I’m team Jess.”
“Plus he’s hot,” she added.
Dougherty’s emphasis on Jess’s evolution reflected a recurring theme among his supporters: his appeal lies not just in his chemistry with Rory, but in his evolution.
“His character arc is the most interesting, and he’s the only one with opinions and a personality, in my opinion,” said Caroline Weaver, who traveled from New York City for the event.
Still, Jess’s supporters weren’t the only ones making their case. Logan had his share of defenders as well.
“He didn’t change himself for Rory. He was just himself, and he held her accountable,” said Travis Doerfler, who traveled with his wife from Arizona.
Others cited Logan’s support for her professional ambitions. Brianna Ennis, who has watched the show about five times, shared that she loved their relationship, particularly the way he “supported her as a reporter.”
No one claimed to be team Dean, for obvious reasons.
Emily Gilmore: A Genuine Villain, or Misunderstood?
Emily and Lorelai Gilmore’s strained mother-daughter relationship is a focal point of the show, as Emily masks her emotions and attempts to manage Lorelai’s life, while Lorelai responds defensively with stubborn independence.
Within the fan community, it is widely debated whether Emily’s behavior signals cruelty—most notably her emotional manipulation and inability to apologize—or if she is simply a product of transmitted trauma and loneliness.
“She is a product of her upbringing, and I think that she did the best she could,” Dougherty reasoned.
Although Emily could have been kinder, Dougherty argued, her flaws are part of what makes her such a compelling character. Her wit provides some of the show’s funniest moments, while her love for her family often emerges beneath the sarcasm.
“She has villainous ways, but she has a good heart, and she became the star that she was because of her strong personality and how much she loves her family,” she maintained.
Among most groups I talked to, Emily was hailed as an icon, a fan favorite. Many praised her memorable lines, while Doerfler went so far as to call her the show’s “MVP.”
“She grew up in a place and time where she didn’t really get to have an opinion, and I appreciate the arc where she becomes herself again,” said Caroline Weaver.
Lauren Spiegel, from Massachusetts, added that Emily’s journey was particularly meaningful, sharing, “I feel like there are probably a lot of older women who can relate to that.”
While fans have grown to love Emily, even for her faults, several fans acknowledged that having an Emily in their own life would not be quite as ideal.
“She’s one of my favorite characters, but if she was in my life, I think it would be pretty difficult,” Ambar del Moral admitted. “You still feel for her, knowing the context of how she grew up.”
Rory Gilmore’s Character Arc: Development or Downfall?
As the show progresses, Rory’s journey can be divided into stages: Chilton Rory, Yale Rory, dropout Rory, and AYITL (A Year in the Life) Rory. For some fans, the early seasons represent Rory at her best. As the series progresses, they argue, her once-endearing ambition gives way to entitlement and increasingly questionable decisions.
“She’s a brat,” declared Spiegel. “She gets everything she wants and then cries when she doesn’t, and she steals boats.”
Weaver was even less forgiving, describing Rory as “truly the worst character.”
Others argue that the perfection we see from her in early seasons was inevitably short-lived, and that her later development is more realistic.
Tammy Adams, who travelled from Ohio, cited Rory’s sexual relationship with Dean, a married man, in season four, which remains a point of controversy surrounding her character.
“Her thing with Dean was a big mistake. It was wrong,” she said. “But let’s take a poll. Who hasn’t made mistakes like that? I feel like it was only a matter of time for her to mess up a bit, which is what you’re supposed to do in your teens.”
Rori McCarthy, a volunteer at the festival, echoed this sentiment.
“I like that in a Year in the Life she still doesn’t have it all together. It’s realistic,” she noted. “You’re still figuring things out throughout your entire life.”
Across all of these debates, one thing remained clear: the energy and life surrounding this nearly two-decades-old show has not died. It has not even begun to fade.
As I spoke to guests, taking in Guilford’s Stars Hollow charm, the camaraderie was palpable, even when people disagreed. As a reporter, it can be challenging to approach groups for interviews, particularly when they’re deep in conversation. Here, it was comforting to be met with pure excitement, joy, and laughter, as fans jumped on the opportunity to discuss their comfort show.
I always thought the show’s greatest accomplishment was creating characters that people could grow up alongside. But maybe it’s creating a community of people who still find reasons to come together over them.
