Although I couldn’t stand Jess for years, I eventually ended up completely reversing my opinion of theGilmore Girlssupporting star thanks to one episode. Ask any fan ofGilmore Girlswho Rory should have ended up with, and you will be liable to get a diverse array of answers. To Dean’s defenders, he is a source of solid support who grounds Rory’s high-minded academic side. To his detractors, Dean is too small-minded and parochial for her. For Logan’s fans, he is charismatic and playful. To his critics, he is a privileged embodiment of the world Lorelai Gilmore rejected.
A Subtle Gilmore Girls Season 2 Moment Makes Lorelai’s Backstory So Much Sadder
In one underrated season 2 moment, Gilmore Girls offered a subtle insight into the secret sadness that underlies Lorelai’s pre-series backstory.
Looking atGilmore Girls’ cast of characters, I was once able to offer a definitive answer. Anyone but Jess, I would have said upon my first viewing of the series. Long before2016’s revival,A Year in the Life, Jess was Luke’s cocky nephew who constantly needled at Rory, made jabs at her school and her friends, and did all he could to upset the idyllic town of Stars Hollow. Now, however, I’m not so sure. Now, I think Rory might be lucky to end up with a guy like Jess and, ironically, he may have outgrown her.
I Was Never Team Jess On Gilmore Girls, Despite Rory Loving Him
Jess Came Across As Standoffish, Angsty, And Aloof
Jess’s first crime was terrible timing, as he arrived during Rory’s tenure at Chilton. Whether it was making an ally of her former bully, Paris, maintaining her close connection to Lane despite the distance between them, or making her relationship with Dean work, Rory could do no wrong during this era. The character’s precociousness hadn’t become exhausting at this point, and it was still endearing to see her struggle with balancing schoolwork, romance, and small-town life safe in the knowledge that everything would always work out alright. Jess, with his bad kid attitude and complicated, contradictory emotions, was a harbinger of darker times.
Like Rory, I couldn’t go back to ignoring the cracks in Gilmore Girls' cheery facade after Jess’s arrival.
I resented Jess making the simple morality ofGilmore Girlsmore complex. From the moment he arrived, Jess upset the peace, pitting the previously supportive Lorelai against her daughter and making the seemingly sweet Dean look close-minded and boorish.Gilmore Girls’ April Nardinimight have had a more explosive impact on the show’s overarching narrative, but Jess was a more conscious chaos agent than Luke’s hapless daughter. He hated the saccharine image of Stars Hollow and its golden child, Rory Gilmore, and, like Rory, I couldn’t go back to ignoring the cracks inGilmore Girls' cheery facade after his arrival.
Gilmore Girls Season 6, Episode 8 Fully Changed My Mind About Jess
Jess Matured More Than Rory In Later Seasons
In season 6, episode 8, “Let Me Hear Your Balalaikas Ringing Out,” Logan and Jess met for the first time in a scene that finally made me understand the former character’s appeal. Jess is a confident author working in publishing by this point, and he is dismayed to hear about Rory’s recent disregard for college, academia, and her ambitions more broadly.I understood why Rory wanted Jess whenGilmore Girlsrevealed he was a committed artist who cared about her, and all of his teenage brooding retroactively seemed understandable. His artistic prowess and publishing industry success contextualized Jess’s struggles.
It seemed pretty clear that Jess hated Stars Hollow because he belonged in the city, and that he acted out because he was sick of the constraints of adolesence.Rory’sA Year in the Lifestorylineproves that her journalistic ambitions weren’t guaranteed to succeed, whereas Jess writing a novel at his young age displayed considerable work ethic and talent. His investment in Rory’s future was also touching, considering it had been two seasons since she ended their romantic relationship for good. Jess cared about Rory even as a friend, ironically proving he might have been her best love interest all along.
Why Rory & Jess Never Could’ve Worked In Gilmore Girls
Rory and Jess’s Maturity Never Quite Aligned Throughout Gilmore Girls
In a brutal turn of events,Jess and Rory never quite made sense inGilmore Girls. When Jess first encountered Rory he might have been smitten with her, but he was too angry, frustrated, and inarticulate to set up a life with her. He didn’t have a clear plan for his future, while she had almost too much ambition and drive, so the pair didn’t make sense together. Then, years afterMitchum warnedGilmore Girls' Roryabout her limitations as a writer, the tables had turned. InA Year in the Life, Rory was a wreck in both professional and personal terms.
Gilmore GirlsandA Year in the Lifeare available to stream on Netflix.
Her career was in shambles and, worse, she didn’t seem all that concerned about it. She complained of setbacks ad nauseam but did little to change her circumstances. She continued an affair with Logan despite having a fiancée while, in contrast, Jess had gone from strength to strength in the intervening years. I was sad to see how disastrous Rory’s journey into adulthood was, but I wasn’t surprised to see that Jess had succeeded during their time apart. In the revival, Jess is a successful novelist who once again helps Rory get her life back on track by advising her to write.
Rory & Jess Could End Up Together If Gilmore Girls Season 9 Happens
A Year in the Life Follow-up Could Make Rory and Jess Work
AlthoughChristopher and Lorelei’s ill-advisedGilmore Girlsmarriageproves that not all the show’s old couples needed another shot,Jess and Rory could still get back together in a ninth season. Rory’s pregnancy will likely lead to her taking things more seriously, while her manuscript could be the shot in the arm that her waning literary career needs. If this is the case, Jess could be open to a romantic reunion between the pair. He seemed to still hold a candle for his high school girlfriend inA Year in the Lifewhen he was advising Rory on her next step.
Jess could potentially help Rory with editing her manuscript.
It is hard to imagine howGilmore Girlsseason 9 could bring Jess and Rory back together after so much time has passed. However, since Rory’sA Year in the Lifeplot ended with her penning a tell-all memoir, Jess could potentially help Rory with editing her manuscript. This would be enough to allow sparks to fly between the pair, and their relationship might prove more fruitful than her earlier romances with Dean and Logan. As long as any future episodes ofGilmore Girlsdon’t force Jess to settle down in Stars Hollow, as I doubt he would survive the town even now.
