Jess Mariano Was Rory's Most Empowering Boyfriend On 'Gilmore Girls', Hands Down

I’m going to be completely honest here. Ever since Milo Ventimiglia revealed that Jess Mariano is in the Gilmore Girls revival (and starring in three of the four episodes, no less), that brooding, hot mess of a character has been on my mind ever since. This isn’t an admission that a woman who turns 30 in less than a month is proud to make, but it’s the absolute truth. It also comes down to more than simply swooning at the potential for Rory to rekindle her romance with the man who was basically her best boyfriend ever (seriously!), or thrilling at the thought of a grown-ass Jess scowling frustrations at the world from only half of his lovely mouth in that battered biker jacket of his. There’s a part of Jess, and a very big part of the relationship he had with Rory, which feels familiar to my own experience, and I feel an intense need to defend every aspect of that.

I appreciate that there’s a sub-sect of Gilmore Girls fans who detest Jess, and I can easily understand why. He could be obnoxious (ugh, don't remind me about that "prank" phase he had when he first joined Stars Hollow), he wasn’t dependable, and his unpredictable, damaged character gave him irrational, impulsive traits which could be heart-wrenching to those who cared about him and those who were ultimately pushed away for their affection. The truth is, though, even for his failings, and perhaps because of his failings, Jess was possibly one of the best boyfriends that Rory could have had at that time.

Though his impulsive nature could be brash and unreliable, it also made him spontaneous and exciting. (I would have given anything as a teenager to have a boyfriend who sprung me with last-minute tickets to see The Distillers. Dreamboat!) Though he carried the insufferable baggage of a damaged cynicism with him wherever he went, it was these qualities which also made him a realist within a town of surreal optimism and daydreamers. Though volatile, he was also resolute, and, though wary of the trappings of emotional investment, he was also carelessly romantic. And you know what? That’s hot as hell.

As a character, Jess was essential for pushing Rory out of her comfort zone and for making her realise her own power, desires, and capabilities as a woman. Prior to Jess, Rory was emotionally immature and dangerously naïve at a crucial time when her life was set to enter the new, demanding phase of college. Knowing Jess gave Rory the harsh dose of reality that she sorely needed and, frankly, helped to mould her into being a tougher, more assertive version of herself.

For instance, it’s doubtful that Rory would have ever had the guts to play Logan so cool at the start of their relationship without Jess’s influence or that she would have figured out how crucial it can be to take risks in order to evolve. (Whether those risks yielded positive or negative results, such as dropping out of Yale or stealing a yacht, is a completely different story.) Jess was a gateway boyfriend, one who introduced her to the fact that life is a balance of good and bad, and that you have to not only be brave enough to follow your heart regardless of the potential results, but also be prepared to face all the disappointment, heartache, and frustration that life can spit back at you when you dare to care enough about something.

I dated a lot of Jess types in my teenage years and early 20s, and, though the majority of them drove me excruciatingly insane or completely broke my heart to the point where I wondered if I would ever actually recover, I appreciate the lessons that each and every one of them taught me. Most of these guys weren’t bad people, and they weren’t horrible boyfriends either. But they were young and impulsive, and they allowed problems from their pasts to influence their present in a way which was suffocating. Though fleeting, I count many of these relationships as being integral to making me the empathic, tough, and gutsy woman that I am today.

I still speak to many of these old boyfriends from time to time, and I’d like to think that my heavy handed, overly emotional influence may have helped push them to figure out their strengths too and to drop some of the baggage which was holding them down. We all deserve to have relationships with friends and lovers who challenge us to be the best we possibly can be. And that process can be painful, whether our hearts get broken in the process or not.

As such, I’m obviously waving a big Team Jess banner for the Gilmore Girls revival and am holding out for the smart, poetic, and creative part of the character to have devoured all the toxic parts of him. Furthermore, I want the woman that he helped Rory to become to find kinship in the identity that Jess has grown into; like estranged love letters lost in the post finally finding their way back to the sender, I suspect that Jess and Rory will have matured into being exactly the right characters at the right time for each other when the revival starts up again.

For those of us who are grateful to the smart, creative, difficult heartbreakers of our youth for making us the badass women we are today, this would be the ultimate tribute and the perfect closure.

Images: Warner Bros. Television; Giphy (3)