There is nothing better than getting cozy, grabbing some snacks, and watching a series you used to love. Shows like Gilmore Girls, which ran for seven seasons and also had a four-part reboot on Netflix in 2016, are rare in the current age of streaming. Now we’re lucky if we get 10 episodes from one season of our favorite shows. Back when Gilmore Girls came out, they were producing 22 episodes a season, resulting in over 150 episodes. I got to bask in the lives of Lorelai and Rory Gilmore and the townspeople of Stars Hollow on a weekly basis for most of the year. It was magnificent.
What I remember most is that I was completely obsessed with Rory’s love life. Jess was my favorite, which explains a lot of my dating life in my 20s, but I digress. It’s now been over 20 years since the first episode aired, and my perspective has shifted. The show is still so heartwarming, funny, and captivating, but it speaks to me from a different place. While the Gilmores are cemented in time, I have grown up and life experiences have inevitably made me see the world in a new light. Watching Rory and Lorelai go through seven years of their life again simultaneously made me realize how much they shaped me and how much we’ve grown apart.
Before we dive into my new perspective on the show, if it’s been a while since you’ve visited Stars Hollow, you can watch a recap of every season on YouTube.
And now, without further ado, here’s what struck me the most when rewatching Gilmore Girls as an adult:
The love triangles are not the point
I’ve been in a lot of discussions recently about love triangles and how most people are over them as a storytelling device. These plotlines have been written time and time again. It would be difficult to name a show in which there isn’t some sort of love triangle, especially in the Gilmore Girls era. Throughout the show, there is always a love interest for Rory. We often see Rory through the lens of the men that are constantly falling in love with her. The bad boy Jess vs. the good boy Dean is a tale as old as time. As I mentioned before, I was very into Jess at the time, much like I was into Chuck Bass in Gossip Girl or Damon in The Vampire Diaries.
Loving the bad boy is a classic pattern many of us fall into and the psychology behind why is something that I would love to do a research paper on one day. Bad boys like Jess typically don’t follow the rules, they don’t care what anyone thinks, and they aren’t afraid to put other people in danger for a little bit of fun. But they also tend to have emotional depth and creative instincts and are exciting to be around. And then there are the good boys like Dean. They thrive on being kind, responsible, and moral, but they sometimes get a reputation for being boring. However, there’s one thing that is certain: Both the bad boy and the good boy tropes in Gilmore Girls are exhibiting major red flags.
Rory’s love life is not something to aspire to
This leads me to my next point. Growing up, all I wanted was to be Rory Gilmore, who manages to be humble, relatable, and good at school, yet also attracts the attention of desirable partners. But now I realize her love life was not relationship goals. It was actually a hot mess.
Dean’s pursuit of Rory is kind of creepy
When rewatching, I noticed that a lot of the flirting and pursuing was done by Jess and Dean. Dean literally watches Rory from afar until he finally approaches her when she accidentally drops her box of school stuff. He already knows a lot about her. It’s kind of creepy and definitely a red flag, whereas I used to think it was romantic. Pursuing a partner until they finally say yes, or being pursued in the same manner, is no longer attractive to me. Mutual attraction and respectful boundaries are more romantic in the long run. I would have been more into the Dean storyline from the beginning if their first meeting was the moment in the hallway when Rory drops the box. Instead, the first time we see Dean, he’s leaning against a wall watching Rory and Lane walk into school, with a look on his face that’s more “evil character from The Vampire Diaries” than “possible love interest.”
Jess and Rory’s constant bickering is no way to flirt
One of my favorite episodes is the 24-hour dance-a-thon, where Lorelai enlists Rory to be her partner. Jess and Dean are both there, Rory and Jess are constantly bickering, and Dean breaks up with Rory in front of everyone, realizing she’s in love with Jess. The bickering between Jess and Rory, like the love triangle, is also a tale as old as time. It normalizes fighting as a form of flirting and becomes a roadblock whenever they’re working through conflict. I was shocked at how much my perception of Jess changed from when I first watched the show. What I once thought was cool and hot was actually just immature and misguided. (Rewatch The Notebook and you’ll see a perfect example of this—I thought it was a great love story but it’s actually an example of a toxic relationship, at least in the couple’s youth.)
Rooting for Rory and Dean comes with its problems
I would also be remiss if I didn’t bring up the shattering moment when Rory loses her virginity to Dean, at a time when he’s married to someone else. Of course, there are major red flags going on there all around. When I was younger, I always rooted for Dean and Rory, even in that moment. I think at the time I didn’t understand the full repercussions of what was happening. But now, Lorelai’s reaction when she realizes what’s happening hits deep, as does Rory’s initial denial of it being a problem. The whole scene highlights how often shows lead us to root for the characters to get together and leave a relationship, without thinking about the other person involved. There’s a very poignant moment where Rory attempts to blame Dean’s wife Lindsay for the affair, and Lorelei shuts it down immediately, proving her hard-earned wisdom. The affair is one of the first times we see Rory make an irreversible mistake, and it sets the tone for the rest of the show.
Rory’s storyline stays consistently rocky
Speaking of huge mistakes, I was relieved later in the series when Rory didn’t accept Logan’s marriage proposal. Logan was the good and bad boy remix on the show, and I’ve always felt fairly neutral about him. So watching it back, I was practically screaming at the screen for Rory not to settle for a life with Logan. So many other shows at the time would have seen their engagement as a happy ending for Rory, but Gilmore Girls did not give in to that pressure. The story lets Rory move forward owning the hot mess that is her love life, not needing to wrap it up in a bow. However, as anyone who watched the reboot can attest, Rory continues to have a rocky love life and career far into adulthood. When I first watched this show growing up, I aspired to be like Rory. Now? Not so much.
Lorelai is way more relatable
When I’m rewatching shows, I always look up how old the characters were when the show began. Lorelai is 32 years old in the first episode, and Rory is 16. While I was close in age to Rory when I originally watched the show, I am now closer in age to Lorelai, and honestly, her story got better with time. Not unlike Rory, Lorelai has quite a complicated love life (including more than a few close calls with marriage). But her relationships aren’t the only thing that defines her; she runs her own business and raises Rory—two things I’d argue she puts before her love life. Every action she takes is not only for Rory but for her own personal growth. Rather than marry Christopher and fall into a life she never wanted, Lorelai chose herself and arguably, the harder path. For that, I respect her character so much more. In almost every decision, Lorelai deeply considers the life she dreams of having for herself and Rory and doesn’t compromise it, because she knows just how much is at stake.
I can now totally get on board with Lorelai’s motivations and gained a new respect for her character when rewatching. I also found myself always agreeing with her when she was arguing with Rory. Like Lorelai, I was absolutely distraught in the first episode when Rory suddenly didn’t want to go to Chilton after just meeting Dean. Especially since, as noted above, Dean was a red flag from the beginning. This teenage crush is something I might have felt when I was Rory’s age, but at the age I’m at now, there is absolutely no way I would give up an opportunity for a person I just met. Lorelai understood this, having been through a life-altering event at Rory’s age, and her wisdom is still relevant—as it is throughout the show, despite Rory not always listening to it.
Stars Hollow does not exist
The ending of the original series sets Rory up to leave home to write for a news outlet while on President Obama’s campaign bus. It was not a bad first job and her choice had nothing to do with Logan or Jess or Dean, which I loved to see when rewatching. In fact, the last episode focuses on the town of Stars Hollow, Rory and Lorelai, and the strength of the life they built for themselves there. That was the true heart of the show. Stars Hollow is small, it’s community-driven, and everyone seems to have their role and know their purpose. It’s a simpler life than the one I grew into as an adult, where I live in a big city, am constantly traveling, and wear more than a few hats.
Back when Gilmore Girls first started, I thought something like Stars Hollow was a place I might be when I reached the ripe old age of 30 and settled down. Hilarious as it is that I thought 30 was a time to settle down (now I hope to never settle down ever), I truly believed that a place and a feeling like Stars Hollow would be plausible. Yes, small towns exist, but I don’t think life will ever be quite like the one Lorelai and Rory had. It’s a show based on reality but also feels more like a fantasy now—one I no longer fantasize about. I’m no longer the kid who wondered what my adult life would be like. Instead, I am living it. And that realization is the biggest gift rewatching Gilmore Girls could have left me with.