This 'Gilmore Girls' Episode Made ‘Shipping Rory & Jess Almost Too Hard To Do

If Reddit fangirling is anything to go by, Jess Mariano the number one favorite Gilmore Girls boyfriend of the show. And sure, why not? He was erudite, rebellious, and almost as consumed by his book obsession as Rory. And yet, if you can make it through the foggy haze of nostalgia and lust that surrounds reminiscing about one Jess Mariano to do a re-watch session, you'll find that things weren't always peachy between the pair. I mean, obviously, because they split up. But, even long before the split, the one Jess and Rory Gilmore Girls episode that made the couple almost too hard to 'ship for me would have to be Season 3, Episode 14 "Swan Song." Mainly because it so wonderfully underscores a very real difference in principles between the pair, a difference that has been the death of so many real-life couples.

While there are many episodes in which Jess does something awful or inconsiderate to Rory, or Rory makes assumptions about Jess, it was in "Swan Song" that both of those behaviors collided to form a clear picture of a problem between the couple that was never resolved by the series. A problem that, without that resolution and compromise, would have made them a poor long-term couple.

This was also the episode where we really learned what a piece of work Jess Mariano could be on a bad day, meaning it became pretty hard thereafter to ever really, truly worship Jess and Rory's connection. Could you really idolize a guy who could make you look terrible in front of your grandma? But don't take it from me. Let's review the whats and the whys and the nos of the episode that had me screaming at the TV.

Essentially, the issue with Rory and Jess boils down to one primary difference between them: Rory worships her family while Jess mostly treats his with contempt. While Rory’s aware that her mother and her grandmother don’t always get on, this doesn’t affect the respect she treats each and every one of the Gilmore clan with. In contrast, Jess is surly at best and downright rude at worst to the one member of his family who really looks out for him: Luke. Jess is also disrespectful of other people’s families. I’d argue that, no matter how much the pair both love literature, that this primary difference is too big for them to have gotten past. And this difference is probably best illustrated in the episode.

It's showcased from the beginning of "Swan Song" onwards. When Emily discovers that Rory has a new boyfriend, she's eager to meet him and cajoles Rory into inviting him to the next week's Friday night dinner. Although Rory feels uncomfortable about it, she cares about her grandma enough to put her own feelings aside. Meanwhile, Jess doesn’t have to hang out with his family, just someone else’s, and this sounds incredibly square to Stars Hollows’ own rebel without a cause.

He does lots of James Dean-esque pouting and posturing before Rory finally manages to close the deal. So, even before anything goes down, Jess is already being pretty provoking, and, as a viewer, you're like "Eh, you've got great cheekbones, but you're such a bummer."

Rory has two incredibly distinctive characteristics. One of those is that she’s a studious bookworm. The other is that she lives for her family. I’d argue that, if Jess had even spent a little time with her (which he had!), he’d be aware of this and that he’d prioritize the same things in her life that she makes a priority. Which is why, when he shows up to Friday night dinner late, with a black eye, and refuses to talk about it, it’s so infuriating. We find out at the end of the episode that he got hit in the eye by a swan, and he doesn’t want to talk about it because it’s so embarrassing and absurd. But he must have known that, by refusing to talk about it, he’d lead Rory’s grandma to draw certain conclusions (that he gets into fights) and Rory to draw even more certain conclusions (that he gets into fights with her ex-boyfriend out of possessiveness and jealousy).

And he probably might have clocked that, given Rory’s faithful hearted nature, she’d probably be so concerned about Dean that she’d jump to conclusions, get emotional, start a fight with him in front of her grandma, and ruin Friday night dinner. Was she right to do so? No. Was it understandable that she did? Yes, just as understandable as it was that Jess would lie to save his own pride. Neither of them come out of this smelling like roses, but it's Jess' disrespect for Rory's family that stays with me to this day.

But it’s not like we didn’t get fair warning about what an asshole Jess could be when it came to family. He had it out for Rory’s best friend, her mom Lorelai, from day one. Remember that episode where he comes over to their house for dinner, steals a beer, and asks Lorelai if she’s sleeping with Luke? Or remember how he tells Luke "you have to fix everyone. You think it makes you a good guy but really, it just makes you a pain in the ass" when Luke’s just trying to be fatherly and give him so advice? So. Much. Ugh. But this was the episode that really rammed it home just how mean Jess could be if family was involved: he made Rory’s grandma think he was trouble, and he made Rory break with Friday night dinner etiquette and get angry and vocal at the dinner table.

In short, by the time you get to the end of this episode, you're almost wishing they weren't a thing. But then you remember the fact that he up how far away Yale was from Stars Hollow ("22.8 miles," if you're wondering) because he was so invested in their connection. The fact that he did that most un-Jess-like of things and asked for time off work to come and meet Rory's grandma on a Friday night. Tthe fact that he has a singularly aesthetically appealing face (translation: he's cute).

Then, you think, "All right. All right Jess Mariano, you're on thin ice, but I'm going to hold the faith."

Sure, Jess could be a real jerk, and this is far from the only episode to make that clear. But you, like me, probably gave him another chance because, like James Dean before him, he was kind of a poser, but also completely charming.

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