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Gilmore Girls fans generally fall into three camps. Some fans think Rory Gilmore belonged with her high school boyfriend, Dean Forrester, while others believe Rory’s bad-boy boyfriend, Jess Mariano was perfect. Another group of fans thinks Rory and Logan Huntzberger were relationship goals. While two of Rory’s relationships lasted years, her relationship with Jess was actually pretty short-lived.

Jess pursued Rory while she was still in a relationship

For the casual viewer, Jess and Rory’s relationship seemed to span several seasons of Gilmore Girls, but in actuality, it didn’t. Their relationship felt long because Jess pursued Rory from the moment he stepped off a bus in Stars Hollow from New York. Rory, however, was still heavily involved with Dean at the time.

Jess’s pursuit of Rory was subtle at first but became more aggressive as time went on. Admittedly, Rory was interested in Jess while she was still dating Dean. Nothing much happened between them before Rory’s big breakup, though. The pair only shared a brief kiss while she was still dating Dean. They didn’t actually get together until their senior year of high school.

Jess and Rory’s official relationship began during their senior year of high school

While Rory and Jess flirted with each other for several months before getting together, they didn’t officially begin dating until after Stars Hollow’s dance marathon. The event took place in the fall, just a few weeks after Rory started her senior year of high school.

While the couple didn’t seem to celebrate an actual anniversary, fans have theorized that they likely began dating in October. They never actually made it to their first anniversary and they never had a proper breakup, either.

The pair broke up shortly before Rory graduated from Chilton

Rory and Jess’ relationship didn’t last that long in the grand scheme of things. In fact, their relationship was the shortest of Rory’s three major romances. Their relationship officially ended just days before Rory graduated from Chilton.


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Jess left Stars Hollow before Rory’s graduation ceremony, which likely took place in early June. If that’s the case, Jess and Rory’s relationship only lasted about seven months. In contrast, Rory dated Dean from October of her sophomore year of high school until her senior year. Their relationship lasted around two years. After briefly reconnecting with Dean, Rory dated Logan Huntzberger throughout her time at Yale. They first became official at the end of her Sophomore year and dated until Rory turned down his marriage proposal at her college graduation. They were together for around two years, too.