With all due to respect the big pregnancy cliffhanger at the end of Gilmore Girls: A Year in the Life, the craziest twist of the four-episode Netflix revival was the reveal that Jess Mariano (Milo Ventimiglia), the former token bad boy boyfriend and all-around punk of Stars Hollow, is actually now a sane voice of reason who is too good for Rory Gilmore (Alexis Bledel).
Of course, Jess' transformation actually began during the original series' run, but it's important to make this distinction now because the revival implied Jess was likely Rory's version of Luke (Scott Patterson) while Logan (Matt Czuchry) was her version of Christopher (David Sutcliffe). And while it's true Rory is more than just her love life, when past and current romantic exploits are given center stage like they were in the revival, you can hardly fault fans for placing so much emphasis on her complicated relationships. However, to fully comprehend why this turning of the tables really matters now, we need to look at where these characters started.
Once upon a time Jess Mariano was the worst thing to ever happen to the small New England town of Stars Hollow and its most revered resident, the angelic and studious Rory Gilmore. He stepped off the bus from New York — the big city! — with a chip on his shoulder the size of the duffle bag that carried his belongings. With a near-permanent scowl and what apparently was a non life-threatening disease that only allowed him to speak in monosyllabic grunts, Jess was an angry teenager with no outlet for said anger so it manifested itself in the form of band T-shirts and sarcasm.
When he arrived in town it was because his mother — Luke's sister — wasn't able to control him any longer, and although we never really found out what exactly Jess was doing in New York that led her to send him to Luke, it's fun to imagine he was running a floating craps game or something equally weird, because despite his status as the town bad boy, Jess wasn't actually all that bad. He earned the title of hoodlum because Stars Hollow is a town where time appears to have stopped and the effects of the outside world don't reach past the town limits. Jess' offenses measured up to disrespecting authority figures, smoking cigarettes whenever the show needed him to, stealing garden gnomes, terrorizing Taylor Doose (which, to be fair, is something everyone does) and drawing some chalk outlines to create fake murder scenes. There's really only so much mischief one can get up to in a town like Stars Hollow. Still, despite this obvious darkness within him, Jess managed to charm Rory.
After months of flirting and courting her through the usual ways — stealing her books to write in the margins, yelling at her mother, outbidding her much taller boyfriend at the Bid-A-Basket Festival so he could eat lunch with her and talk about Ernest Hemingway — Jess eventually managed to win Rory's heart and the two embarked on a relationship... after Dean (Jared Padalecki) dumped Rory because she wasn't woman enough to admit she had feelings for a guy most of the town thought was a punk. This probably should have been our first clue Rory wasn't the saint she'd been presented as.
Though their romance was the shortest of Rory's three longterm relationships -- lasting for just two-thirds of the show's third season — it was such a deep connection that many fans immediately took to 'shipping them hard — though in the early 2000s, no one called it that. In contrast to good old boy Dean — who was, in all fairness, not written to be dumb until the show needed him to be in order to highlight Jess' connection with Rory — Jess was the sexy, intelligent and experienced boyfriend who pushed Rory out of her comfort zone. However, by the end of the third season there were plans to spin him off into his own series focusing on his life in California with his father. The project was never picked up to series and so the way Jess was written out — skipping town on a bus without saying goodbye to Rory after A) being told he wasn't going to graduate and therefore couldn't take Rory to the prom, and B) taking out his issues regarding said non-graduation on Rory (and later Dean's face) — was viewed more as the ultimate dick move rather than a dick move that was also a poorly designed spin-off attempt.
Jess' decision to leave Stars Hollow without a word was without a doubt the worst possible decision he could have made at that point, but Jess was a teenage boy and teenage boys are notoriously stupid. Jess was his own worst enemy, and he eventually paid the price for it when, after returning in Season 4 and confessing his love for Rory, he later asked her to run away with him and she rejected him before falling into bed with a then-married Dean. Rory was an idiot even if an entire town refused to admit it. Though for what it's worth, this time Lorelai (Lauren Graham) and the entire Gilmore Girls fandom were in agreement over this obvious misstep.
However, Rory turning Jess down was also the best thing that could have happened to him. By the time the character returned in Season 6, he was a changed man. In the time since Rory's rejection he had found a job at a small publishing press and even written a book, which he claimed he couldn't have done without her. He'd finally managed to carve out a life for himself that proved he was no longer the jaded teenager acting out but a responsible adult who chose to walk away from fights rather than engage in crossfire. It was during a fateful dinner with Rory and Logan that Jess proved to be the bigger man before getting through to Rory and convincing her to reenroll at Yale. With the exception of her ill-fated trip to Philadelphia later on in which she kissed Jess in an attempt to get back at Logan, that was the end of Jess' story. It was what it was. Until the revival.
Now a relatively successful adult, Jess has a stable career and solid relationships with both his mother and his uncle. He has become a voice of reason and a sounding board for his friends and family thanks to his unique perspective as an outsider who sees through Stars Hollow's admittedly infectious whimsy. He has twice put Rory back on track — it was also Jess who pushed Rory to write about her life with Lorelai in the revival, thus giving her life direction and helping her to tap into her formerly missing passion — and has proven to be quite helpful when it comes to Luke, too. It seems that in the time since we'd seen him in Philadelphia, Jess has matured even more and so in the grand scheme of things, Jess finally became the man many fans always knew he could be. His return also couldn't have come at a better time for Rory.
It was abundantly clear by his arrival in "Summer" that the former good girl wasn't capable of making good decisions on her own. In addition to the affair with Logan, she was a failing freelance journalist who took a handout from Mitchum Huntzberger and who also thought she was too good for a HelloGiggles-like website. When she was desperate enough to finally meet with the founder of the site, she assumed she'd be offered the job without actually having to interview for it, which further highlighted her sense of entitlement. In a not-all-shocking twist, Rory wasn't hired. To add fuel to the fire, she fell asleep while interviewing a source and then later slept with another. For once Jess looked like the shining star of Stars Hollow and Rory was the aimless problem child with a growing pile of poor life choices at her feet. The tables had turned considerably, and yet, Jess still loved her.
But the implication that Jess harbors feelings for Rory 15 years after they dated is a little surprising given there wasn't a single romantic beat in their interactions in the revival and they hadn't seen each other in at least four years. This brings up the question of whether or not Jess has been sitting around waiting for Rory all this time or if his feelings have simply been reignited. For what it's worth, it does seem more like the latter, as if being in her orbit is all it takes to wake up dormant feelings that have really never gone away. But it's almost too hard to believe that with that face, those biceps and a book in his back pocket Jess is still single at 32. What's more confusing though is why he's pining for Rory at all.
It's true Rory isn't wildly changed and there's evidence that points to her frequently undermining the perfect facade we all bought into during the show's original run — which could be spun as Jess always loving Rory, flaws and all — but between the selfishness, the cheating on her understanding boyfriend with an engaged man who never gave her any indication he wanted more, and an obnoxious sense of entitlement, Rory was obviously unlikeable in the revival in a way that she wasn't in the original series. And yet that longing look through the window revealed Jess has, as Usher once famously sang in the rain, got it bad.
That Jess could be Rory's version of Luke will probably please the fervent #TeamJess faction of Gilmore Girls fans, and it's kind of sweet to think that one day they'll again find happiness again like a warped live-action fairy tale. After all, what is Stars Hollow if not a theatrical dreamland full of enchantment? But this raises the question of whether or not Jess should wait for Rory while she attempts to figure out the next stage of her life, which will now include another man's baby. Luke waited years for Lorelai and we considered it romantic, but should Jess wait for Rory?
On one hand, he has come too far on his own to be saddled with Rory's growing problems, even if he appears to know exactly what she needs. So it's not going too far to suggest he, a well-adjusted man capable of doling out sound advice and who is finally comfortable with who he is, should maybe reconsider his feelings and get as far away from Rory and Stars Hollow as possible for fear of being dragged down with her. On the other hand, love makes you do the wacky and as Jess told Rory all those years ago in Philadelphia, "It's what it is. You, me."
Jess is a grown man capable of making his own decisions — and making good decisions — but because of the open-ended nature of "Fall", we may never know what happens next between them. However, one thing is certain: Until Rory figures out her issues and gets herself fully on track, Jess will remain much, much too good for her.
All four episodes of Gilmore Girls: A Year in the Life are currently streaming on Netflix.