Although Jess and Rory’s relationship is one of the best love stories inGilmore Girls, Jess’s surprisingly sudden exit never made all that much sense. Theentire cast ofGilmore Girlshad compelling subplots, but Lorelai and Rory’s love lives were never far from the show’s focus. There is a reason that theGilmore Girlsfan base still argues online about who Rory should have ended up with, and this is because the show devoted a lot of screen time to fleshing out her relationships with potential paramours like Logan, Jess, and Dean.
Two Of Gilmore Girls' Most Unloved Stories Were Virtually Identical
April Nardini’s arrival and Rory’s relationship with Marty and Lucy both arrived around the same time and highlighted the same Gilmore Girls problem.
EvenDean’s briefA Year in the Lifereturnprompted anger from some viewers who wanted Rory to return to her first love, despite the very different paths their adult lives took.Logan’s exit before theGilmore Girlsfinalewas equally contentious, even though Rory turning down his marriage proposal did fit with her character arc. As a career-oriented young woman, Rory wanted to prioritize her work life over her love life and Logan wasn’t open to a long-distance relationship. As sad as it was, this breakup made sense, unlike one even more infamous love interest exit.
Jess and Rory’s Breakup Justified His Gilmore Girls Exit
Jess first leftGilmore Girlsin season 3, although he returned repeatedly in season 4, and this summary alone hints at how awkward and strange the character’s arc was. Actor Milo Ventimiglia famously wantedGilmore Girlsto kill off Jess, a hilariously dark twist that would have jarred with the show’s cozy, low-stakes tone. Although Jess never did get hit by a bus as his actor suggested, he did end his relationship with Rory on bad terms in season 3. Jess left Stars Hollow to pursue a relationship with his estranged father, but never properly ended his dalliance with Rory.
Jess’s Gilmore Girls redemption makes more sense considering the behind-the-scenes context.
This played into the town’s conviction that Jess was a bad kid, but future seasons soon disproved this theory. As Rory’s life began to spiral out of control when she stole a yacht and earned community service as a result, Jess got a job in publishing and wrote his first novel after moving to New York. By the time he met her in season 6, Jess was the responsible adult and passionate literary enthusiast, while Rory was the rebellious ne’er-do-well Stars Hollow treated Jess as.Jess’sGilmore Girlsredemptionmakes more sense considering the behind-the-scenes context.
Where Jess Goes After Leaving Stars Hollow
Jess Moves To New York And Becomes A Writer
Jess was originally supposed to move to California in pursuit of his father, and his misadventures would have been chronicled in aGilmore Girlsspinoff show titledWindward Circle.Season 3, episode 21, “Here Comes the Son,” was intended to be a backdoor pilot for Jess’sGilmore Girlsspinoff, but the series wasn’t picked up. SinceWindward Circlenever happened, Jess instead returns to Stars Hollow in season 4 before eventually moving on to New York. He seemingly stays there off-screen for much of seasons 5 and 6, occasionally returning to Stars Hollow for brief guest appearances.
Jess Has Appearances In Later Seasons Of Gilmore Girls & A Year In The Life
Jess Returned For The Gilmore Girls Revival
Although Jess never lived in Stars Hollow for long after season 3, he was a frequent visitor. Jess appears in both seasons 4 and 6 as well as inRory’sA Year in the Lifestory, where it is implied that he still has a crush on her. By this stage, Jess is a successful author, and it is he who tells Rory that she ought to write a memoir about her experiences with Lorelai and Stars Hollow. This draws Rory out of the creative funk that she spent the rest of the revival stuck in.
Why Milo Ventimiglia Exited Gilmore Girls In Season 3
Milo Ventimiglia’s Exit Facilitated Jess’s Spinoff
Jess ending Rory’s writer’s block lends credence to the idea that they may eventually end up together, butA Year in the Lifeends with Rory single and pregnant. If a future revival does pair up the couple, it will be tough for the show to explain why Jess left all those years ago. In reality, it appears that Milo Ventimiglia’s exit was predicated on the series pickup ofWindward Circle. This would explain why Jess returned relatively swiftly and why he remained an occasional guest star throughout the rest of the show’s run.
Rumors swirled online about Ventimiglia being offered a six-season contract withGilmore Girlsand refusing it, but no credible source has verified this. There is a lot of documentation aboutWindward Circle’s existence and its backdoor pilot is tough to ignore, so it is most likely the case that Ventimiglia never intended to permanently leave the world ofGilmore Girlsat all. Instead, the actor hoped to star in its spinoff and so he returned to the original show when theGilmore Girlsspinoff never came to fruition.
