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As one of the biggest things to ever hit Stars Hollow, the arrival of the bad boy Jess Mariano (played by Milo Ventimiglia) in Gilmore Girls changed everything. With his heavy Rebel Without a Cause vibe, good looks, and passion for literature, it didn’t take long for Jess and Rory (Alexis Bledel) to get together.

'Gilmore Girls: A Year in the Life' actors Milo Ventimiglia as Jess Mariano and Scott Patterson as Luke Danes
Jess Mariano and Scott Patterson as Luke Danes | Saeed Adyani/Netflix

But, after their teen romance ended, Jess was painted as perpetually single throughout the rest of the original series and Gilmore Girls: A Year in the Life—an idea that just doesn’t make sense.  

Jess carried a torch for Rory throughout Gilmore Girls

Dumped on Luke’s doorstep by his flaky mother (Luke’s sister), Liz, Jess arrived in Stars Hollow with a serious chip on his shoulder. His attitude got him a bad rap in the bucolic little town.

Still, he and Rory formed a bond that quickly surpassed her picture-perfect yet unstimulating relationship with her first boyfriend, Dean Forester (Jared Padalecki). As noted by Gilmore Girls Fandom, “although Rory never says it out loud, she feels like she and Jess are kindred spirits, sharing very similar interests.”

Acknowledging the writing on the wall, Dean dumps Rory, and Rory and Jess become a couple. However, Jess soon disappears to California to live with his long-lost father, and Rory reluctantly moves on. Her story continues, and Rory begins attending Yale, where she meets Logan Huntzberger (Matt Czuchry). 

Jess, however, never seems to move on. He returns from California and asks Rory to run away with him, but she denies him, opting to get back together with Dean. Rory then later shows up in Philadelphia, where Jess is living, and the pair share a kiss, but Rory again dismisses him to return to Logan. 

Despite everything Jess has going for him (which, let’s face it, is a lot), his character is never seen in another relationship in Gilmore Girls and is left in an abyss of waiting for Rory.

‘Gilmore Girls: A Year in the Life’ hinted that Jess was still waiting for Rory

Even years—decades—later, when Gilmore Girls: A Year in the Life takes place, Jess is still single. Now in her thirties and the throes of a serious rut, Rory takes over the Stars Hollow Gazette, where she is busy withering when Jess strolls into her life once again.

While Rory desperately slurps down her liquor at noon and wallows in her failures during the revival’s “Summer” installment, Jess appears to have grown into even more of a catch than he was before: He is now more handsome than ever and a successful author. Yet, when Rory asks him about his personal life, he is still, illogically and inexplicably, single. 

Will Gilmore Girls’ Rory and Jess ever get their Lorelai-and-Luke ending?

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But while Jess remaining single doesn’t make any sense, his perpetual pining for Rory may reveal Gilmore Girls’ creator Amy Sherman-Palladino’s true endgame for both him and Rory. Despite Rory’s widely discussed unattractiveness as a character (fan forums have discussed at length her entitlement and habitual cheating), she is still her mother’s daughter, which bodes well for her.

Lorelai, too, showed flippant disregard when suddenly calling things off with Max and later (sort of) cheating on Luke with Christopher, but she got her happy ending. And, like Luke spent decades pining for Lorelai, Jess may just be as hooked on his Gilmore girl as Luke was on his. This may explain Sherman-Palladino’s chosen ending for Jess in Gilmore Girls: A Year in the Life’s “Fall.”  

Brought together again in preparation for Luke and Lorelai’s wedding, Jess excuses himself from the pre-marital chaos only to linger on the Gilmores’ front porch with his military-style bag slung over his shoulder, staring longingly at Rory through the window. The scene mirrors one from early in the original series when Jess is leaving Stars Hollow, and Rory, behind for California. The symbolism may mean that Jess has now returned for good.

Certainly, he has proven himself to be as steadfastly devoted to Rory as Luke was to Lorelai, and should Gilmore Girls: A Year in the Life get a sequel (as the cliffhanger ending allows for), it is likely that Jess and Rory get their happily ever after as well.  

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