"Good night, Dodger." || Rory & Jess

Aww, little Jess!


It's a well-known fact that for as long as I've been acquainted with the TV show Gilmore Girls, I have been firmly on the Team Jess side of things.  None of Rory's love interests are perfect guys ⎼ none of them ⎼ and all of them make stupid mistakes, but I've always been adamant that Rory Should End Up With Jess And No One Else.

And I still think that Rory Should End Up With Jess And No One Else.  But I'm a little more clear-sighted about it now.

Because during my most recent bout of interest in the series (I tend to cycle through stories that I like, experiencing phases of renewed enthusiasm and then returning to a fairly dispassionate and long-standing appreciation that no longer approaches fervor in its intensity), I started to question my long-standing conviction.

Is Jess really the undeniably best option for Rory?  Was she actually misguided in refusing to reenter their romantic relationship?

I started wondering, and that right seriously.  I never stopped liking Jess as a character, but I did start to doubt that I had been justified in my impassioned defense of him and quasi-judgment of Rory's distant behavior towards him after their break-up.

The reason for this is that I realized something important, something that needs to be considered and addressed in any analysis of Rory's romantic decisions or in any declaration of preference regarding her love life's potential resolution:  Jess treated Rory really, really badly when they were a couple.  

Like, the boy done messed up.   A lot.

And regardless of her own issues (of which, I assure you, there are plenty), and regardless of his eventual repentance and growth (on which, more later), Rory is under no obligation whatsoever to give Jess her trust again once he has betrayed it.  She just isn't.  And she shouldn't be.  And as much as I want them to be a couple, and as much as I think they have the best chance of good, lasting happiness together out of all Rory's boyfriends (now that Jess has undergone SOOOO much maturation), it's unfair of me to judge Rory for not trusting that the boy who let her down so many times has truly grown into the responsible and committed man he claims to be, a man who would cherish her the way she deserves to be cherished.

Now, granted, he has grown up.  He has straightened his life out.  And he would cherish her that way.  I think he always will.

The 8 books Rory and Jess name drop in the ‘Gilmore Girls’ revival | Revelist

But, although I think he's certainly earned one, he's really not entitled to a second chance.  That's up to Rory, and if she decides that she either is not ready to offer it or that she probably never will be, I've got to respect that just like Jess does.

And on the other hand, maybe it's not even about trust, for Rory.  Maybe she's just truly realized that she doesn't love Jess in a romantic way anymore and that he's not the best, safest place for her heart.  Though I might completely disagree with her, and though she's gone so crazily off the rails of the maturity she had when she was younger that we're probably justified in doubting her clarity of insight into the actual workings of her heart, it's still ultimately her decision.


Lemme 'splain.

As a teenager, Jess is going through all kinds of personal junk. He has a terrible parental situation, and he's understandably bitter and jaded and aggressive and Ticked at Life. He has a great deal of potential (which Rory sees), much of which he deliberately squanders (which Rory also sees). He's rebellious, he's unreliable, he's probably involved in more than a few sub-legal activities. He's problematic.

His feelings for Rory are genuine ⎼ I will always believe that ⎼ but he lacks, at the age of seventeen, the backbone to follow through on them and be the boyfriend she deserves. (Or, heck, be the nephew that Luke deserves ⎼ let's not even get started on that ⎼ or the resident that Stars Hollow deserves.) He's caustic, dismissive of practically everybody but Rory and Luke (whom he very unwillingly loves and respects), and trouble-making. He leaves Rory out in the cold, relationally speaking, whenever he's in one of his moods. Like Rory vents to her mom, he refuses to communicate with her, preferring to fall back on his trusty sarcasm and angsty eye-rolls, and that ubiquitous adolescent mantra, "Whatever."  He's very angry, and his instinct is to deflect.

The dude has issues, y'all. 

Jess! Love him! So Yummy!

And that's not to say that he doesn't have worth, or that he's heartless.  He doesn't always treat Rory badly.  He has great value, he does (occasionally) try, he is grateful to Luke even if he's terrible at expressing it, and, again, life hasn't been super kind to him. That in no way excuses him, but it does explain him. He's got a lot of baggage to work through.

But, then he does work through it.  He does put in effort.  He does get his act together.  He recognizes the problems with his behavior and his choices, and he actually implements change.  After he's lost most of his contact with Rory.  It's not like he's doing this in a desperate attempt to get her back.  He probably is hoping he can have a chance to win her over again ⎼ and I do not fault the boy if so ⎼ but ultimately he's not doing this for her.  He's doing this for him.  He realizes that his lifestyle is bad.  He realizes that he's made mistakes and let down the people who invested and believed in him the most, and he decides that he genuinely wants to try to make as many amends as he can for those errors.

He takes his sinking boat and points it home, as the song goes, and he gets it there.  He patches things up with Luke.  He writes a book.  He makes something of himself.  And he doesn't forget that he owes a lot of his success to the faith Rory and Luke had in him.

And all this while, as Jess is rebuilding his life and improving himself as a person, Rory is doing pretty much the exact opposite. 

Rory is really mature and wholesome when she's younger.  She's studious, responsible, ambitious, hard-working, and kind.  But after she leaves Dean for Jess, her new relationship sours, and Dean marries young, she starts losing her way.

Ever since Jess entered the scene, Rory has seemed unable to decide what she wants, romantically speaking.  From then on, it's as if she wants to hang onto "all the boys she's loved before," unwilling to relinquish any of them wholeheartedly.  And that causes problems.  She has an affair with married Dean.  That falls through, thankfully, but even after it does, she no longer seems like the Rory we knew.  She's still pretty sweet, but she seems confused as to what she wants out of life now.

Rory, “Lazy-Hazy-Crazy Days”

She meets Logan.  (I have only seen seasons 1-4 and the recent Netflix revival in their entirety; I've seen a couple episodes and clips from 5-8 and know the general storylines.)  Not having really watched the inception of their relationship, it may be unfair of me to judge it, but I do know that it starts bringing out some unsavory aspects of Rory's character.  She starts breaking the law, fooling around, and even quits her Ivy League school for practically no reason.  (Again, this is the gist I've gained from summaries and such.)


Because here are two people who have loved each other, who certainly seem to be well-matched as a couple, who start developing on converse sides of the maturity spectrum after they break up. WHYYYYYYYYY. 

Now, thankfully, Rory doesn't stay completely off-course.  She does eventually get somewhat back on track.

And who gets her there?


Let Me Hear Your Balalaikas Ringing Out and Summer
"wHY DiD yOu DrOp oUt Of YaLE?!?!?!?!"

Jess, who's come around a couple quiet times since their last big confrontation.  Jess, who's been focusing on other aspects of his life, fixing it.  Jess, who isn't about to stand idly by and let Rory run aground if he can help at all.

Both times that Rory seems lost and directionless, Jess unassumingly steps up to confront her ⎼ not in a judgmental way, not in a heavy-handed way, just in the straightforward humility of a friend who still cares about her, even if they're not a couple anymore.

And Rory listens to him.  Because she knows that he knows her well, and even if she doesn't trust him romantically (or is no longer interested in him romantically, or whatever the case may be), she values his opinion.

And I can't help but feel that that's because, deep down, she knows she's not quite ready to let go of him or of the possibility for another relationship with him at some point down the road.  Because they would be good together.  He made a lot of mistakes their first go-round, and that's significant.  But he's also changed a lot since then, and he's proven himself to be reliable and to care unselfishly for her.  That's significant, too.

He was patient and listened to Rory and tried to eat what she brought in her picnic basket.

The ending to the revival was an incredibly open-ended cliffhanger, with Rory revealing to her mom, in the last seconds of the last episode, that she's pregnant.  (By whom, we don't know, but Logan seems the most likely possibility.)  While I have read that the whole team is actually discussing the possibility of a second revival at some point in time, nothing definite has come out that I know of.  So, for now at least, we're all left to draw our own conclusions as to how Rory's life will pan out.

Many people, it seems, suspect that this whole situation ⎼ Rory pregnant and involved with a not-wholly-appropriate "bad(ish) boy" while a pretty stable and dependable guy is waiting right in front of her ⎼ mirrors the Lorelai/Christopher/Luke triangle.  Personally, I think that's pretty probable.  I don't think Logan and Rory are going to work out long-term, and I think Jess is obviously in this for the long haul (however much he denies it).  I don't think it's far-fetched at all to predict that one day, when he's completely regained her trust, Rory might just recognize that she still loves Jess and that he's worth another try.

That's what I hope for, anyway.

What do you think?
Whose "team" are you on in regard to Rory?
Do you want another revival as much as I do?


  1. I am 100% Team Jess. Forever and always. I love that him not controlling his inner turmoil was shown as having consequences, and then he overcame it and was so mature and amazing??? I think she should have taken him back in the later season. I know she was hurt by him, and then that she was in a relationship with Logan (so I guess go her for being faithful).


    1. Yaaaaaass, girl! I think they would be good together. But, as you say, I guess good for her in that particular instance.


  2. I wholeheartedly agree with your appraisal of Jess and Rory's relationship. And I've always been Team Jess.

  3. TEAM JESS 100%

    i love him and Rory together so much! i think i would like to see another revival. It would be interesting to see where the writers take the characters.

    You made a lot of good points and i loved it!!


    1. Wouldn't it be interesting to see what they would do with it? (Provided, of course, that they don't do anything too heinous. :-P)

      Thanks so much! Appreciated your comment. :)

  4. This is a Very Good Post, and I like it. I especially like how you said that Rory isn't obligated to give Jess a second chance, romantically--cuz that is TRUE. No one ever 'earns' a second chance. You may be given one, but you don't get to demand one.

    I actually think Rory shouldn't be with anybody--not Jess, not Logan, not Dean, not anybody--because I think she is the kind of person who needs to be alone and self-sufficient and learn to live with herself, and not keep losing herself in her relationships.

    But that's *sips tea a la Kermit* Just My Opinion. ;-P

    1. Aww, thanks! I thought about you a couple times while writing it and was interested to see what your perspective would be. ;)

      It is true, and it's something I hadn't fully grasped there for a while. Personally, I think Jess deserves a second chance, but I also appreciate Rory's prerogative to not give him one. Because, as you said, she's not obligated to.

      I definitely think Rory could benefit from an extended period of singleness--relationships do seem to distract her at this point in her life, like you point out--but eventually I'd like to see her with somebody. Preferably Jess. ;D

    2. Great point! Yes! Maybe she WOULD be more ready for a relationship after a long period of singleness & introspection . . .

  5. Yaaas! Great job, Olivia! :) You summed up the Jess-Rory relationship very well! I agree, Jess was very immature and rough around the edges when he was young, while Rory was more responsible and sweet. However, as they got older their roles almost completely flipped. Now Jess was the responsible, caring guy that got Rory back on track when others didn't. Because he knew her well, because he loved her, because he actually cared more about her than he did if she got back together with him or not. *cries* But yes, like you said, he had treated Rory pretty badly when they were in a relationship, so Rory absolutely has every right to have nothing to do with him if she chooses. (It is really hard to see Rory go from the sweet, innocent little girl to the kind of messed up- but in the process of redemption- woman. *so many feelings*) Anyways, this comment is getting Waaay too rambly, so suffice it to say that I appreciate your wonderfully written post, and you summed up their relationship beautifully.
    Go team Jess! ;)

    1. "because he actually cared more about her than he did if she got back together with him or not." << GIIRL. *cries with you* But yes. Very true.

      Indeed he did, young lad. *maternal sigh* Like you said, it's tough to see Rory "go downhill," but I like how you point out that she's also in the process of redemption.

      No, it wasn't! I loved it; thanks so much for reading and commenting. :D <3

  6. Ahhh! So many deep thoughts!!! <3 <3

    I'm currently part way through season 4, but I will admit I read the entirety of all this. I don't have access (atm) to any further seasons OR the revival and I can't wait that long. xD

    I've only seen Dean and Jess with Rory, and I'm DEFINITELY Team Jess! For sure! At what point does Jess come back to Rory? 'Cause I feel like he disappeared really quickly in season 3 (or was it the start of season 4... I don't remember). I was hoping he'd make an appearance before season 4 ends. And I'm a little disappointed (okay, A LOT) to hear that Rory goes downhill the older she gets. Nnnooo. That's not the way things are supposed to go!

    I currently have Many Feelings but can't seem to put them into words. So just, YES. And a big sigh.

    1. Haha, I feel that about not being able to wait that long. ;)

      He does make a few appearances before season four ends, including the one where he (essentially) asks Rory to get back together with him. YES, it's really frustrating about Rory. I MIGHT understand the choice to make her "go that route," but I think it definitely needs to be resolved more than it has been so far.

      I feel that, too. For sure. *sighs with you*


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