The real reason Jess left Stars Hollow.
Although Jess and Rory’s relationship is one of the best love stories in Gilmore Girls, Jess’s surprisingly sudden exit never made all that much sense. The entire cast of Gilmore Girls had compelling subplots, but Lorelai and Rory’s love lives were never far from the show’s focus.
1 Even Dean’s brief A Year in the Life return prompted 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 the Gilmore Girls finale was 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.
Where Jess Goes After Leaving Stars Hollow Jess Moves To New York And Becomes A Writer ✕ Remove Ads Jess was originally supposed to move to California in pursuit of his father, and his misadventures would have been chronicled in a Gilmore Girls spinoff show titled Windward Circle. Season 3, episode 21, “Here Comes the Son,” was intended to be a backdoor pilot for Jess’s Gilmore Girls spinoff, but the series wasn’t picked up.
Why Milo Ventimiglia Exited Gilmore Girls In Season 3 Milo Ventimiglia’s Exit Facilitated Jess’s Spinoff Close Jess ending Rory’s writer’s block lends credence to the idea that they may eventually end up together, but A Year in the Life ends 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.
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