Remember the days of debating which boyfriend was The One for Rory Gilmore? Well, maybe those days aren’t totally behind us — it’s still very much an ongoing debate now that Gilmore Girls fans anxiously await the Netflix four-part revival series. (At least in my head.)
Back when the original series was airing, I argued none of them were worth her time — not Dean, not Logan, not even Jess. Instead, I theorized that she would meet someone better suited for her while covering the campaign trail as a journalist, which is where the show left off. But that was before I had any experience with relationships myself — the good, the bad, the toxic … and the boring. Now that I’m many years older and a mom to two girls, my opinion has shifted.
If life was like a television drama, perfectly scripted with memorable punch lines and wacky characters; if all three men — Dean, Logan, and Jess — were standing on my daughter’s doorstep the summer after college graduation, asking for a second (or third) chance, I’d tell her to do the unthinkable: Stick with Jess.
1. Let’s face it — Dean was lovable, but not exactly evolving.
Don’t get me wrong; Dean was a gentleman. He was tall and handsome, with a boyish smile that admittedly made me swoon when the camera first panned over that ridiculously cute face, staring at Rory from the school steps. He was the quintessential good guy; a mom’s dream: respectful, understanding, communicative, and committed.
In other words: A perfect first boyfriend.
But here’s the catch: There was never any real growth with Dean. He didn’t evolve at the same pace as Rory, which I’ve learned can lead to both boredom and resentment. Dean supported Rory, but he didn’t challenge her or push her into new experiences. (Unless you count that whole Donna Reed situation; but I digress.)
And let’s not forget, while Rory may have wanted the best for Dean, she also wanted to change him. I don’t want my daughter seeking out relationships that require changing the other person just to get them to fit into her version of “the perfect guy/girl.” I want my daughter to have dreams and goals of her own, and I want her partner to have that same desire for learning and growing as a person.
2. Logan may have been motivated and ambitious, but man was he stubborn.
I gotta be honest, Logan was the worst. Unlike humble Dean, Logan was arrogant and entitled. Yes, he had a certain allure: a squinty-eyed smile and boyish charm, paired with perfectly tousled hair. He was also extremely smart and witty, with big plans for his future. It was all really promising in the beginning, once he finally committed to Rory.
But the longer he stayed with Rory, the more his sense of entitlement shined through, which is a huge turnoff. (Plus, he cheated on her during their one-second break — so that right there should be Reason No. 1 to give him the thumbs down.)
As a parent, I bristle at the possibility of his return in the new reboot. Although I could (maybe) get past his brief infidelity and childish behavior, I would not be able to get past his inability to stand up for Rory when she really needed support. At the very least, Logan should have stood up to his own dad for not accepting Rory into his family, and told her that his father was completely wrong when he insulted her — she did have what it takes to be a journalist. (Instead, he helped her steal a yacht.)
And lastly (because no, I’m not done with Logan just yet), I still have a bone to pick with him over having his life with Rory all planned out in San Francisco — without actually consulting her on any of it. I want my daughter to be with a man who doesn’t vie for control in even the most subtle of ways.
3. Sure, Jess was flawed. But above all, he was sincere — and that makes all the difference.
Jess came into Rory’s life at the worst possible time. Things with Dean were running pretty smoothly, she had finally caught up at school … it was all (relatively) good. Now enter “bad boy” Jess. At that moment in time, there would have been no way in hell I’d cheer on that relationship.
If a Jess-like character rolled up into my daughter’s life in these circumstances, my mom instincts would have gone into overdrive, and I would have done my best to keep them apart. I would hope it was a phase. I would tell myself, It’s high school. What high school relationship is drama-free?
Of course, Jess came with some obvious flaws — like leaving Rory at home on Friday nights or shutting down when things got hard; but he was also just a teenager. Even for adults, communicating feelings and having uncomfortable discussions are tough.
The truth is, Jess challenged Rory in new ways, and she did the same for him. They were equals, and their conversations were intellectual. They pushed one another into new experiences and they gave each other space to pursue their own dreams. And who can forget how Jess helped Rory get back on track, by calling her out on her hasty decision to leave Yale?
If you ask me, grown-up Jess — a few years out of teendom and (hopefully) a few years wiser — would be my pick. For my daughter, for Rory, for anyone.
Relationships can be hard and challenging and full of amazing highs and serious lows. They require daily work and communication. But ultimately, I want my daughter to wind up with someone who supports her, lifts her up, calls her out on her crap, and challenges her.
A Jess will do that. And I hope, once we return to Stars Hollow later this year, Rory finally realizes that, too.