What If Rory Had Stayed With Jess?
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VOICE OVER: Emily Brayton
WRITTEN BY: Savannah Sher
What if Rory had stayed with Jess? It's a question that every Gilmore Girls fan ponders. We're taking a deep dive into what we think would have happened if these two had managed to make it work. MsMojo discusses what would've happened if Rory had stayed with Jess. Do you think Rory should've stayed with Jess? Let us know in the comments!
Have you ever thought about how things would have panned out if this fan favorite “Gilmore Girls” couple had stayed together? Welcome to MsMojo and today we’re looking at What If Rory Had Stayed With Jess?
For this essay, we’re taking a deep dive into what we think would have happened if these two had managed to make it work.
Fans of “Gilmore Girls” divide easily into three camps: Team Dean, Team Jess, and Team Logan. Over the years, it seems like the Rory/Dean shippers have slowly faded away and the Jess fans have multiplied. Since the release of “Gilmore Girls: A Year in the Life” in 2016, the fires have only been fueled further because of the way these two exes were portrayed.
But things weren’t always positive (or even healthy) between Rory and Jess, and if we look back to the beginning of their relationship we can find a lot of indications that they aren’t exactly a great match. From the very first time we meet Jess, he is sullen, sarcastic and honestly, kind of a jerk. As the seasons progressed, however, Jess grew into a mature and lovable character and managed to make us forget his youthful transgressions from earlier in the show.
So how would things have looked if these two had never broken up? Or if they had taken time apart and eventually gotten back together? First, let’s take a look at some of the negatives. The most obvious change would be that if this couple had just stayed together from the point that they dated in high school, they would have missed out on having other relationships that helped them grow and realize what they truly wanted. In Rory’s case, it would mean that she was with Jess throughout her time at Yale, which would mean she wouldn’t have dated Logan. We can of course see the positives of this relationship never taking place, since Logan’s family’s treatment of Rory kind of derailed her life for a while there, causing her to doubt her abilities as a journalist and temporarily drop out of school. It also would have meant that she’d get to miss out on that awful cringe-worthy proposal from Logan at the end of the series.
But more realistically, let’s look at a situation where Rory and Jess did break up, at least for a while, and had the opportunity to develop separately before deciding to be together. The biggest potential issue we see here is that while Rory and Jess have so much in common, they may have some fundamental differences. While both of them have adventurous spirits, we think that deep down, Rory will want to settle in Stars Hollow just like her mom, and there’s a strong possibility that Jess would never want to do that. Throughout the series, he disappointed Rory by disappearing on her several times, and while we know that he has grown up since then, he may always have a tendency to leave when the going gets tough.
On top of that, there’s the question of starting a family. Would these two be able to agree on whether and when to have kids? We can definitely imagine Rory wanting children at some point, and in the revival series the story ends with her announcing her pregnancy. Jess definitely never indicated at any point in the show’s run that he was inclined towards settling down and starting a family, but based on how much he has changed in other ways, it doesn’t seem outside the realm of possibility. Considering how his relationships developed with Luke and even his mom and Lorelai, we can imagine that over time he would become more family oriented.
Now that we’ve talked about the bad stuff, let’s focus on the positive. Above all, Rory and Jess had incredible chemistry, and cared deeply for each other. Almost right from the beginning, it was clear that there was something special between them, even though Rory was with Dean at the time. They were clearly passionate about one another, and we can imagine that would have continued even if they were together for years. They also shared a lot in common, from their love of reading to their desire to see the world. First off, can you imagine the kind of badass library that these two would have in their home? Between the two of them, they would definitely manage to collect a massive collection of books over the years. We can imagine them travelling the world together in their younger years and expanding their worldviews.
Most importantly, though, we can be 100% certain that these two would have pushed themselves to be the best they can be. From the very beginning, Jess took Rory out of her comfort zone, and Rory pushed Jess to use his sharp intellect to further his academic life. When they meet again years later, Jess has published a book and he credits Rory for giving him the inspiration to do so. At the same time, he questions the life she is living in working for the DAR and staying with her grandparents after leaving Yale. His harsh critique of what she was doing was what ended up pushing her to rethink her plans. When we saw Rory again in “A Year in the Life,” she was really flailing when it came to her career and fans were almost unanimously unhappy with where she had ended up in life. If she had been with Jess, however, we know that she would have already achieved greater things. In fact, one of the high points of the revival was Jess encouraging Rory to write a book about her life experiences. Overall, we can say without a doubt that Rory and Jess would have become their best selves if they were together.
What do you think? How would this relationship look years later? Feel free to weigh in in the comments!
For this essay, we’re taking a deep dive into what we think would have happened if these two had managed to make it work.
Fans of “Gilmore Girls” divide easily into three camps: Team Dean, Team Jess, and Team Logan. Over the years, it seems like the Rory/Dean shippers have slowly faded away and the Jess fans have multiplied. Since the release of “Gilmore Girls: A Year in the Life” in 2016, the fires have only been fueled further because of the way these two exes were portrayed.
But things weren’t always positive (or even healthy) between Rory and Jess, and if we look back to the beginning of their relationship we can find a lot of indications that they aren’t exactly a great match. From the very first time we meet Jess, he is sullen, sarcastic and honestly, kind of a jerk. As the seasons progressed, however, Jess grew into a mature and lovable character and managed to make us forget his youthful transgressions from earlier in the show.
So how would things have looked if these two had never broken up? Or if they had taken time apart and eventually gotten back together? First, let’s take a look at some of the negatives. The most obvious change would be that if this couple had just stayed together from the point that they dated in high school, they would have missed out on having other relationships that helped them grow and realize what they truly wanted. In Rory’s case, it would mean that she was with Jess throughout her time at Yale, which would mean she wouldn’t have dated Logan. We can of course see the positives of this relationship never taking place, since Logan’s family’s treatment of Rory kind of derailed her life for a while there, causing her to doubt her abilities as a journalist and temporarily drop out of school. It also would have meant that she’d get to miss out on that awful cringe-worthy proposal from Logan at the end of the series.
But more realistically, let’s look at a situation where Rory and Jess did break up, at least for a while, and had the opportunity to develop separately before deciding to be together. The biggest potential issue we see here is that while Rory and Jess have so much in common, they may have some fundamental differences. While both of them have adventurous spirits, we think that deep down, Rory will want to settle in Stars Hollow just like her mom, and there’s a strong possibility that Jess would never want to do that. Throughout the series, he disappointed Rory by disappearing on her several times, and while we know that he has grown up since then, he may always have a tendency to leave when the going gets tough.
On top of that, there’s the question of starting a family. Would these two be able to agree on whether and when to have kids? We can definitely imagine Rory wanting children at some point, and in the revival series the story ends with her announcing her pregnancy. Jess definitely never indicated at any point in the show’s run that he was inclined towards settling down and starting a family, but based on how much he has changed in other ways, it doesn’t seem outside the realm of possibility. Considering how his relationships developed with Luke and even his mom and Lorelai, we can imagine that over time he would become more family oriented.
Now that we’ve talked about the bad stuff, let’s focus on the positive. Above all, Rory and Jess had incredible chemistry, and cared deeply for each other. Almost right from the beginning, it was clear that there was something special between them, even though Rory was with Dean at the time. They were clearly passionate about one another, and we can imagine that would have continued even if they were together for years. They also shared a lot in common, from their love of reading to their desire to see the world. First off, can you imagine the kind of badass library that these two would have in their home? Between the two of them, they would definitely manage to collect a massive collection of books over the years. We can imagine them travelling the world together in their younger years and expanding their worldviews.
Most importantly, though, we can be 100% certain that these two would have pushed themselves to be the best they can be. From the very beginning, Jess took Rory out of her comfort zone, and Rory pushed Jess to use his sharp intellect to further his academic life. When they meet again years later, Jess has published a book and he credits Rory for giving him the inspiration to do so. At the same time, he questions the life she is living in working for the DAR and staying with her grandparents after leaving Yale. His harsh critique of what she was doing was what ended up pushing her to rethink her plans. When we saw Rory again in “A Year in the Life,” she was really flailing when it came to her career and fans were almost unanimously unhappy with where she had ended up in life. If she had been with Jess, however, we know that she would have already achieved greater things. In fact, one of the high points of the revival was Jess encouraging Rory to write a book about her life experiences. Overall, we can say without a doubt that Rory and Jess would have become their best selves if they were together.
What do you think? How would this relationship look years later? Feel free to weigh in in the comments!
