Rory Gilmore’s love life remains a topic of conversation for Gilmore Girls fans. It has been over 20 years since fans met Rory Gilmore as a high school sophomore and bid her farewell, in the original series, as a college graduate. During the show’s initial run, Rory had three main love interests.
Dean Forrester served as her first significant love interest, while Jess Mariano was the bad boy who stole her away from Dean. Later, she hooked up with the sophisticated and exceedingly wealthy Logan Huntzberger. While Logan was her most significant love, many fans believe Jess was the man for her. We’ve put together a timeline of Rory Gilmore and Jess Mariano’s love story for your consideration.
Jess Mariano appeared in Stars Hollow in season 2 of ‘Gilmore Girls’
Jess Mariano first appeared in season 2 of Gilmore Girls. As Luke Danes’ troubled nephew, Jess made short work of causing a stir in Stars Hollow. The New Yorker didn’t want to spend his time in the tiny hamlet of Stars Hollow, and he made his feelings known. Still, he was instantly interested in Rory Gilmore.
Rory and Jess formed a strange, albeit casual, friendship pretty quickly. Their friendship caused a rift between Rory and her high school sweetheart, Dean Forrester. It quickly became apparent that Jess wasn’t the only one interested. Rory had a thing for Luke’s nephew, too. The love triangle between Dean, Rory, and Jess is still discussed today. Still, little happened, aside from a single kiss, between Jess and Rory until season 3.
Jess and Rory didn’t get together until season 3, though
While Jess and Rory were interested in each other, their relationship didn’t blossom until season 3. During Stars Hollow’s annual 24-hour dance marathon, Dean Forrest broke up with Rory when it became clear that she was interested in Jess.
Once her relationship with Dean ended, she was free to hook up with Jess. That is precisely what she did. The romance was far from perfect, though. Jess withheld from Rory, acted aloof, and eventually left Stars Hollow after he learned he wouldn’t graduate from high school with his class. His departure was sudden, and he never bothered to end his relationship with Rory. The duo dated for around six months.
Jess Mariano asked Rory Gilmore to run away with him in season 4
Jess’ sudden departure from Stars Hollow and the end of his relationship with Rory Gilmore was pretty harsh. Even fans of the couple agree that the troubled teen owed his then-girlfriend an explanation. He wasn’t gone forever, though.
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After a few chance encounters, Jess traveled to New Haven to find Rory and asked her to run away with him. The spur-of-the-moment proposition caught Rory off-guard. She refused, telling Jess she didn’t want to be with him. He disappeared into the night. Later, Rory slept with her married ex-boyfriend, and no one mentioned Jess again for a long while.
Jess reappeared in season 6 of ‘Gilmore Girls’
Jess didn’t reappear in Rory’s life in any significant way until season 6 of Gilmore Girls. After publishing his first book, Jess sought out Rory to show her what he had accomplished, only to learn she had dropped out of Yale and was spending all her time hanging out with her college beau. He later yelled at her, insisting she had become someone she wasn’t.
Later in the season, Rory traveled to Philadelphia, looking for Jess, after she learned Logan had hooked up with several girls after their first breakup. The meetup ended with Rory returning to Connecticut to figure things out with Logan. That was the last fans saw of Jess Mariano until the Netflix revival nine years later.
Could Jess Mariano and Rory Gilmore get together in a second revival season?
While Jess did appear in Gilmore Girls: A Year in the Life, he didn’t play a major role in Rory’s life. He did show up to give some good advice and suggest Rory pen a novel, though. All grown up and far more mature, Gilmore Girls fans argued that Jess had become ‘too good” for the listless and directionless Rory. Is that the case, though? It’s hard to say since we saw so little of Jess.
Is there hope for them in a second revival, though? While Netflix has yet to announce a second revival season, several clues suggest it could still happen. If it does, some fans hope a Jess and Rory love story could be in the works. We don’t think that’s likely. When the first revival ended, Rory was pregnant, presumably with Logan Huntzberger’s baby. If history were to repeat itself completely, Rory would end up with Jess eventually, just as Lorelai Gilmore ended up with Luke Danes.
Still, that feels a bit too simple, especially for the show’s creator, Amy Sherman-Palladino. In 2016, Sherman-Palladino told Time that Jess and Rory’s first boyfriend, Dean Forrester, was meant to show her development and represent who she was at that moment. If that’s the case, Rory should have outgrown Jess, meaning they wouldn’t end up together. However, fans would need a second revival to see how it actually plays out.
