As you already know, I’m no fan of Dean Forester. So when it comes to picking the best of Rory Gilmore's beaus, who do I prefer? I have to admit I’ve been on Team Logan ever since Matt Czuchry joined the Gilmore Girls cast way back in 2004, but I’ve always had mixed feelings about most people’s favourite: Jess Mariano (Milo Ventimiglia). This is partially because my eldest sister (the one who got me hooked on GG in the first place) never liked him, but also because the first time I watched the show, my 12 year old heart couldn’t understand the appeal of Jess’ “bad boy” persona. Even though I’ve been appreciating him more during my current re-watch, I’m still not entirely convinced that Jess is the best, so I pulled a Rory and made a list of his pros and cons.
P.S. I enlisted two of my GG-loving pals to give me some insight as to why they’re charter members of Team Jess. Special thanks to Alex and Emillie for trying their hardest to get me on their side (P.S. It's working).
When it came to chemistry, Rory and Jess were explosive. Perhaps it was because they were dating in real life, or maybe it was just excellent casting. Either way, their romance was palpable, even before they were officially together. It was obvious from the start that Jess was super into Rory, and she fought it for as long as she could, but they couldn’t resist their attraction to each other. If nothing else, at least his attention got Rory out of her semi-abusive relationship with boring Dean.
Jess Mariano wasn’t always the boyfriend Rory wanted. He didn’t call on time, he didn’t always show up, and he didn’t take pride in the town festivals. Still, he was the boyfriend Rory needed—and still does.
In his teenage years, Jess was the picture of troubled youth. Not that you could blame him, with a flighty mom, a whisper of a dad, and a life spent growing up alone in one of the world’s biggest cities. He stole gnomes and skipped school and took life as it came to him. In comparison to our favorite doe eyed seventeen year old (at the time), he shouldn’t have fit at all. But he was witty, and he read like she did, and he listened to her music, and the two fit better than a coffee cup in Lorelai’s hand.
That almost nonsensical compatibility isn’t what made Jess Rory’s OTP, though. Instead, it was the fact that he challenged her. When she was dating Donna-Reed-daydreaming Dean, Jess disrupted their (already doomed) relationship by reminding her of all the things she wanted that three kids and a mortgage weren’t going to give her. When she dropped out of Yale, stole a yacht, and followed in the footsteps of silver spoon bred Logan, it was Jess who reminded her where she came from. And when she found herself back in Stars Hollow at 30, running a long dead local paper, and still searching for her underwear, Jess reminded her that she was still a contender. Jess showed up at all the pivotal times of Rory’s life, whether as a boyfriend or a trusted ally, because Jess is the only person who got what Rory was about. He was the only person who loved her enough to set her back on the track she’d lost sight of. He was the only person who made her see that life wasn’t all town adoration and Chinese takeout. Jess is the boyfriend that grows up with you, and helps you become the version of yourself you always wanted to be. Jess is the boyfriend we all need, and I like to think he’s the Luke to Rory’s Lorelai, the ultimate endgame, the man who will raise Rory’s baby into another generation of strong, powerful, Gilmore’s. (And I definitely have not started dating anyone because of their likeness to Jess, whoever told you that is a liar.)
- Emillie Marvel
I mean...he reads a lot so he can keep up with Rory’s literary habits (though I still can’t forgive him from stealing/borrowing her book and then WRITING IN IT, WHAT KIND OF MONSTER DOES THAT??), and he’s just an overall intelligent guy. Even though he drops out of high school, he proves to be an above average student...he just lacks the motivation. We know that, in the future, Jess works in publishing (owns a publishing house?) and is a successful writer, so at least he puts his brains and talents to good use.
Whether it was convincing her to go back to Yale in season six, or giving her the perfect idea for her book in the revival, Jess always had Rory’s best interests at heart. He encouraged her to be her best self and, even if she didn’t end up breaking her own boundaries like she did with Logan, Rory’s life was admittedly better with Jess in her corner. He didn’t hold her back, but he didn’t pressure her either (in that way, at least...), and they were very comfortable with each other.
Out of the three boyfriends, Jess was the best for Rory. He always pushed her to be the best version of herself, and to chase after what she wanted instead of following others. He was the only one who'd tell her how it was and didn't try to protect her from the world, or manipulate her for his own gain. Sure, he did some stupid things and was problematic just like all of Rory’s boyfriends, but back then he was a kid with a troubled life, and he grew out of that—in the revival he’s shown to be possibly the most stable and together character out of everyone. Not letting his past define him is a mark of true growth and character.
He was intellectually her equal, and challenged her—which is really important in any relationship. In doing so, he represented everything Rory could be: fearless, independent, and unapologetically herself. Instead of trying to change her, he was always the one asking what she wanted, to think of herself more. That kind of selfishness is healthy; it stops you from getting backed into a corner where you make rash decisions and act out (*cough* yacht joyride anyone?). There’s a difference between being nice and being supportive—Rory’s always been coddled and sheltered, and a bit of tough love from him has always been exactly what she needed. Shielding someone from the actions of their decisions isn’t a viable or healthy way to go through life, and it shows an enormous amount of respect and integrity to stand up to the ones you love and tell them the truth. It’ll only make them better people; as much as I love the citizens of Stars Hollow and their quirks, over-coddling was their biggest flaw when it came to Rory, and I only wish Rory had more people in her life like Jess. Maybe she would have made better choices.
Team Jess all the way!
- Alex Bear
Growing Up is Hard
Jess isn’t the easiest person to get along with (see CONS), but he grows and matures as the series goes on. His relationship with Luke was one of the best parts of the revival – when they (SPOILER ALERT?) hugged upon his arrival in “Summer”, I just about wept. They had their rough moments, but ultimately Jess gave his uncle the love he deserved. Just like with Rory – it wasn’t always smooth sailing between them, but he tried to make it work, even when everyone else (*cough Lorelai cough*) was against them.
He’s Attractive (I Guess)
I’ve never been super into Milo Ventimiglia, but I can see why people are attracted to him on a physical level. He does the broody thing very well, but that’s a trait I seem to find more appealing in (stereotypical YA) novels and less in real life.
He’s a Jerk (at first)
During his first few appearances, Jess is not the nicest person. He’s straight-up disrespectful to Lorelai (in his defense, even HE could see she and Luke were Meant To Be...he just didn’t point it out in the nicest way), and is constantly rude to poor Luke who is struggling to give this kid a break even though he’s in over his head when it comes to raising a teen. The worst, of course, is when he comes back in season four and basically makes Luke feel like a complete failure and it makes me so mad every time. And while it is somewhat romantic, you have to remember that he tries to woo Rory while she’s IN A RELATIONSHIP.
Of course, Jess's attitude led to one of the best scenes in the entire series, so I guess it wasn't all bad:
"Mr. Reliable" is a Bit of a Stretch
Jess is referred to as “Mr. Reliable” during his time working at Walmart and it’s hilarious on so many levels. He’s not actually that reliable – he takes off at least three times, without talking to Rory about it (admittedly, the first time, they’re not together so he doesn’t owe her anything, but still), and that last disappearance really throws her for a loop. There’s also the time she goes to a hockey game because he said he’d call and then he ignores her for most of the day (he makes up for it with concert tickets, but you can see their relationship start to crack).
Pressuring Someone isn’t Cool
The number one moment that makes it hard to be fully Team Jess is that time at the party when he tries to pressure Rory into having sex...even when she distinctly says “NO”. He makes her (and the viewers) uncomfortable when he reacts poorly to her rejection and then he picks a fight with Dean (who always wants to fight so it’s not actually Jess’ fault) and it all gets very messy.
Jess does have more pros than cons, and Alex and Emillie present some extremely convincing arguments, but I’m still waffling. I have a feeling that by the time I finish my re-watch, I'll be firmly on Team Jess.