Rewatching Gilmore Girls’ cast of characters are all interesting, fully fleshed-out figures, the show’s true stars are Lorelai, Rory, and Emily. All three of the Gilmore women can be frustrating and lovable in equal measure, but I think it’s fair to say that Rory is the one who underwent the most intense character devolution throughout the original series and its 2016 revival, A Year in the Life.

To be fair to Rory, this isn't just because her Gilmore Girls: A Year in the Life story was a letdown. To an extent, Rory’s arc always needed to make her more believably flawed. In seasons 1-3, Rory is initially portrayed as a perfect, morally upright paragon of humanity. Every random citizen in Stars Hollow and her grandparents treat her as such, which becomes more notably discordant later on in the series when she starts to make some pretty bad decisions. Whether it is dating Jess or taking a break from Yale, Rory makes plenty of few questionable choices.

Why Rory Sleeping With Dean Is The Worst Moment Of Her Story

Rory’s Decision To Sleep With Dean Is A Low Point

However, these decisions are mostly presented positively or neutrally until one pivotal point. In season 4, episode 22, “Raincoats and Recipes,” Rory has sex for the first time with a married Dean. It's a turning point for her Gilmore Girls portrayal as, throughout season 5 and the rest of the series, her behavior is presented in a more critical light. Rory is still young and immature, and there is no doubt that people make mistakes at such a tender age. However, it is not so much Rory sleeping with Dean as her response to it that solidifies its negative impact.

It goes without saying that Dean is entirely at fault in his and Rory’s affair, since Rory isn’t married. However, I still can’t help but notice that everyone from Lorelai to the people of Stars Hollow to even Jess all view her differently after this point. What makes this ironic is not just the fact that Rory’s A Year in the Life story went on to effectively recreate the same plot, but that the season 4 finale’s twist isn’t particularly surprising in the first place. Upon a re-watch, I was shocked by how much it was foreshadowed.

I Should've Known Rory & Dean Was Coming After His Bachelor Party

Dean And Rory’s Reunion Was Unfortunately Foreshadowed

In season 4, episode 4, “Chicken or Beef?,” Dean mumbles about “Rory” when he's drunk at his bachelor party. It is clear from that point forward that season 4 is going back to the Rory/Dean romance, and since he's marrying Lindsey, it's obvious that this subplot is headed toward a story where either Dean cheats with Rory or leaves Lindsey. Dean was never likely to leave Lindsay since, while he was always portrayed as somewhat dim-witted, he knew that Rory wasn't about to change her life plans to accommodate living in Stars Hollow with him.

While there are plenty of Gilmore Girls season 4, it is a rough year for Rory’s always tumultuous love life. She and Jess have their most dysfunctional period in late season 3 and, by season 4, the couple have broken up. Jess might mature enough to tell Rory that he loves her in episode 13, "Nag Hammadi is Where They Found the Gnostic Gospels," but she still turns him down when he suggests moving to New York with him.

In retrospect, it is obvious that Rory, wounded and insecure after the end of her relationship with Jess, is on a crash course with her past.

This occurs in episode 21, “Last Week Fights, This Week Tights,” only an episode before her affair with Dean begins. In retrospect, it is obvious that Rory, wounded and insecure after the end of her relationship with Jess, is on a crash course with her past. Seeing Dean seemingly happy with someone else makes Rory jealous of the attention Lindsay receives from her former love interest, resulting in that uniquely unpleasant, possessive line “He's my Dean!” when she is confronted about his infidelity.

There Was A Lot Of Setup For Rory & Dean's Cheating Story

Dean and Rory’s Affair Was Almost Inevitable In Retrospect

Throughout season 4, Gilmore Girls repeatedly foreshadows the inevitable events of its finale. The tension between Dean and Rory gradually builds and builds with scenes like her calling him on spring break and him returning that call, the pair talking while he's working at the inn, and her outrage at him not going to college. Dean saying Rory is the only one who really cares about what's best for him is, with hindsight, a pretty clear turning point.

However, it is important to recall just how innocent both Rory and Dean are made out to be until this point. On first watch, viewers wouldn't dream of Rory sleeping with a married man, and until now, Dean has been portrayed as the so-called good guy in contrast to Jess’s supposed bad boy.”As such, the obvious conclusion still took me by surprise.

A Year In The Life Made Rory & Dean's Cheating Story Way Worse

Rory’s Attitude To Infidelity Never Changed

While it leads to a pretty intense fight between Lorelai and Rory, the affair’s aftermath proves that this isn’t a story Gilmore Girls could have done without. Rory’s nonchalant attitude toward partaking in infidelity in late season 4 is paid off in A Year in the Life, wherein she sleeps with Logan while both of them are in relationships. This is markedly worse considering Rory is also dating someone this time, but it is portrayed as a much less serious infraction.

By the time A Year in the Life takes place, any lingering image of Rory as an idealized heroine is long gone. The entitled streak she always possessed is front and center in the revival, where she is insulted by an employer asking why they should take a chance on her at a job interview. Rory cheating on Paul in the revival is less surprising than her sleeping with Dean even though, on paper, sleeping with Dean was objectively not as bad.

Rory cheating on Paul to sleep with Logan should seem much worse, but it is much less surprising since seasons 5, 6, and 7 foregrounded her flaws.

After all, Dean chose to cheat on his wife and Rory was just the single, available person involved. Rory cheating on Paul to sleep with Logan should seem much worse, but it is much less surprising since seasons 5, 6, and 7 foregrounded her flaws after her idealized depiction in seasons 1-3. Rory was never the same after the Gilmore Girls season 4 finale, but I can now see how the show told viewers where it was going well in advance.