When Jess was first introduced on Gilmore Girls, I hated him. I knew he was going to replace Dean as Rory's love interest and I hated how long they dragged out the love triangle. Rory kissed Jess while she was still with Dean which yes, is on Rory for initiating it, but it made me hate Jess more. Over the summer I overheard my coworkers talking about how Jess was the best guy in the show, which prompted me to write a long (never posted) blog about all of the problems with Jess and how he treated Rory, and how uncomfortable their fights made me. Having been in a relationship where I was treated similarly, I couldn't see how Jess's "bad boy" demeanor won so many people over when he treated Rory like crap. At one point I specifically remember telling myself that there was nothing the writers could possibly do to redeem Jess as a character in my eyes.
This was all before Jess's return in Season 4.
Jess didn't win me over immediately. I don't remember my exact reaction to his initial return, where he tells Rory he loves her and then immediately drives away, but I probably thought he was stupid. It was Jess coming to Rory's dorm and trying to tell her how he's changed and was ready to treat her as she deserves that cracked my cold heart a bit. I remember tearing up and being shocked that I actually felt bad for him. But his words were genuine (and Milo Ventimiglia being so darn cute and so darn good at acting the scene helped, I'm sure).
Jess returns again in season 6, this time much calmer and more obviously matured as a person. He tells Rory he's written a book and couldn't have done it without her. The scene is sweet, but the clincher is when Rory attempts to return the book as he leaves and he tells her "that one's yours". Sigh. I'm still mad at Logan for ruining the dinner between Jess and Rory that followed- he's a huge dick and I don't blame Jess for hating him. Every scene with Jess kept me wanting more scenes with Jess and more development of that story, but the incredible development of his character was mostly wasted as he ended up more of a plot device for conflict in Rory and Logan's relationship than anything else. Plus he only appears in one more episode for the entire original run (SIGH!).
The last time we see Jess, he's working a good job in Philly and insisting to pay back Luke for all that he gave him while he lived in Stars Hollow. Rory shows up and Jess still very clearly has feelings for her. Rory allows him to get his hopes up and kiss her, to which Rory responds "I can't even cheat on him like he cheated on me," meaning she's there to get back at Logan. What the fuck, Rory. I understand that she's confused about her feelings and what to do, but if she's so easily able to tell Jess that she's in love with Logan and can't break up with him then what the fuck, Rory. She's now used Jess and made him an unwilling participant in cheating in her second relationship (he kisses her, but is reasonably not aware she's still with Logan).
Jess isn't in any more of Gilmore Girls, a travesty.
But A Year in the Life was just released. Jess is still super cute. He and Luke are shown to have a great relationship, and he and Rory are still friends (though they don't see each other much). Rory, of course, has a boyfriend who she is cheating on with Logan and refuses to break up with because she 'forgets'. This was an unfunny running joke, making Rory now a three-time cheater in her own relationships (and don't forget, she broke up a marriage!) Rory is also the other woman in Logan's engagement, meaning that her devastation over Logan's cheating in college taught her nothing and she's fine with being a shitty person. And I'm pretty sure we were supposed to sympathize with Rory for cheating on someone while helping someone else cheat for an entire year in the story's time. They never even give Logan's fiancée a face, so you're really not meant to feel bad for her.
In the end, it's heavily implied that Jess is still in love with Rory, and Rory reveals to her mom that she's pregnant with (what is likely) Logan's child.
Should Gilmore Girls continue, Rory is being angled to end up with Jess even though she's having someone else's kid. Why did anyone, character or writer, wish to make Rory's situation the same as her mother's? Why did they make Rory such a terrible person? Why is Jess still in love with her after all this time? I agree, Rory was pretty great when Jess and Rory were first together. But how many years have passed? Twelve? Fourteen? Jess obviously isn't aware that Rory has been the other woman in, and cheated in, so many other relationships, but the writers are. And Jess is still in love with Rory. Rory is not a good person. She has proven herself as not having integrity in relationships. So Jess raising another man's child with Rory doesn't sit right when up until now Rory has regressed, not become a better person.
It hurts me, too, because I want Jess to be happy and get what he wants. But Rory should just be with Logan at this point. They're clearly good together (I say this spitefully- I really hated the cheating storyline) and now having a child together.
This is not to say I wouldn't have wanted Rory and Jess together. I think they've destroyed Rory's character and that Jess has matured so far beyond her at this point that they need to do better by him.
What are everyone's thoughts on the finale? Any differing viewpoints? I know Amy Sherman-Palladino said that the last four words of AYITL would be the last four words, but do you think Netflix will want to keep going? Do you think Jess is as great as I do?
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