Does Jess Actually Want to Be with Rory?

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Last week, Milo Ventimiglia made some comments about Jess’ return to Gilmore Girls: A Year in the Life, which prompted many to again think that Jess may be the “end game” for Rory. Milo has previously stated his opinion that he believed “it was never going to be Jess,” and though he does affirm that Rory will make a choice, he’s always said he was “popping in” to Stars Hollow, so that has felt (to me, at least) more temporary. 

On August 19th, Milo Ventimiglia went to Wizard World Chicago where he talked at greater length about his return to Gilmore Girls, adding that yes, Kirk is still crazy, but also giving us something to think about. He was quoted as saying:

And you know what? That’s a super important question. It’s not just Rory who has a choice. Jess has a choice. And would Jess choose Rory?

Milo talking about Jess/ what it was like returning to Gilmore girls at wizard world comic con today.

A video posted by gilmore girls (@jess.confessions) on

Milo talking about Gilmore girls revival part 2.

A video posted by gilmore girls (@jess.confessions) on

In another interview with InStyle, Milo talks about just how much Jess has grown. And perhaps he’s grown away from Rory?

“Jess got to play around and experience a whole lot. From battling with his Uncle Luke to finding love with Rory, he was working out his own demons that sent him on his way to be this young son of a gun.”

“And as he kind of stripped away all this anger in his life from the hard times he was put through—with being estranged from his father, his mom driving him nuts, being put into a new environment, and just wanting to be on his own—he turned out to be a very, very great young man.”

“I think the journey from being angry to being content and smiling through life was something that was always fun for me to discover and play and get into.”

Now, don’t go saying I’m not #TeamJess here, I just want to stimulate a discussion. What do you think??

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19 thoughts on “Does Jess Actually Want to Be with Rory?

  • August 24, 2016 at 1:33 pm
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    Honestly, I have no idea. Personally, I love Jess and I would LOVE him to end up with Rory. However, I feel from everything I’ve heard so far about the revival, Rory is going to be with Logan. Obviously I’m just guessing and I wish I didn’t think this, but that’s what I’m feeling anyway.

    By the way, I think it is interesting how Milo brought that up. While we’re all thinking about who Rory would choose, no one is ever thinking that maybe Dean/Jess/Logan may no longer want to be with Rory.

    #TeamJess

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  • August 24, 2016 at 3:21 pm
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    I’m 1000% team jess too and as much as I want them together, I want jess happy with someone who loves him back the way he deserves. And I never thought of that way – the jess/Logan/dean pov. What if all three guys did move on and didn’t want to be with her? What if they decided to move on from her and not one and be happy? That’s for sure an interesting way of looking at it even though we do know she ends up with an ex.

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  • August 24, 2016 at 3:36 pm
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    I’ve thought many times — and not bashing Rory here — but what about if she isn’t good enough for him? 2016 Jess. (And I loved the previous Jess(es), so…I am biased.)

    It would be nice, no matter what happens, to have her chase him — if it comes to that.

    I swing daily about Rory/Jess or Rory/Logan endgame. This isn’t real life and that leads me to believe (as characters and with the fan base excited and watching) that she’ll direct herself toward one of them. I know what ASP said about not catering to the fans, but she clearly had an idea about the ending in 2006, and that, to me, had to include one of these guys. She had no idea it would be 9 years later. But I think she’s going to go with the guy she had planned for Rory in Season 6, moving into 7. And that sure — if you watch Season 6, be Logan. But what do I know???

    I actually don’t think it’ll be “endgame” but more…this may work. With Jess.

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  • August 24, 2016 at 3:38 pm
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    I should say I goofed and sent my note too soon. My sentence should say: And that sure — if you watch Season 6, is not going to be Logan. Based on how it left that season and how much Jess seemed to be the guy to me. Going with Gilmore Guys here: after Season 6, it was clearly Jess from a writing standpoint.

    But, again, what do I know???

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  • August 25, 2016 at 1:21 am
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    Wow,interesting. We never really thought that there is a chance that any of Rory’s guys wouldn’t want to be with her…and I think that is because they always seemed crazy for her,even after breaking ups.Actually,I was always a little jelous of Rory (but not just for that :)
    Anyhow,I hope that Jess will be the final choice,although Logan also can be a fine match.But I have always felt a little sorry for Dean,as he was just the perfect boyfriend (as he treated Rory,what he’s done for her/a car for example/,and he loved her practically from the moment he first saw her and later on the whole show),and Rory dumped him for Jess,what was not Dean’s fault at all…

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  • August 25, 2016 at 1:24 am
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    I don’t see how after Season 6 it was Jess. Milo had no interest in coming back. We’d seen him twice in 2 years. Amy had spent 2 years building up Logan. She had Rory explicitly say that she was in love with Logan to the point she couldn’t even revenge cheat with Jess in Season 6. ASP seemed to write every Jess appearance after Season 3 as if it was his last. See also Rory saying she didn’t want to be with him in Season 4. It wouldn’t make sense to have the character repeatedly reject Jess only to end up with him in the end. We also have to remember Vineyard Valentine where Rory thinks Logan is the one for her. Season 6 ends with Logan and Rory strong, in love, and Jess out of the picture.

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  • August 25, 2016 at 2:00 am
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    I’m really teams Jess and I have not even thought that Jess would be the one who does not want Rory now. I have always thought that the decision will be Rory’s and that Jess can get his heart broken because of her. But when I think about it, I really like the idea of Jess rejects Rory now. It would somehow make their relationship even more interesting. But most important for me is that those two are endgame.

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  • August 25, 2016 at 4:57 am
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    I’m Team Jess:) have been for a long time. I don’t mind Logan so if she chooses Logan I’ll be sad but okay with it. I really her to choose Jess though but I’m really nervous how it’s going to play out. I’m going to be holding a pillow the whole time during the revival haha.

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  • August 25, 2016 at 9:21 am
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    I feel that Rory and Logan will be great match. Logan and Rory is in love with each other and never cheated on. Logan wanted to settle down although Rory was not ready that time. After she explores a while she will be ready to settle down.

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  • August 25, 2016 at 1:21 pm
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    It’s an interesting point. All seven seasons involve Dean, Jess and Logan being Team Rory pretty much all the time. However, it’s been a while! (Is it ten years in the revival as well as for real?) I think it’s going depend on who they end up being. Jess in season 6 had changed a great deal, but he was still very much Team Rory. There’s still a decade for him to change more in though and also for Rory to have changed. I think I’d like it if at least one of the three suitors wasn’t Team Rory now, as I think that would be new, interesting and realistic.

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  • August 25, 2016 at 4:38 pm
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    I’m loving this new season will happen. I watched all the old seasons again and now I have new impressions about the characters. I was #teamdean while the series was in the beginning, twisted nose to Jess and Logan at first, then started to like them. If we take into account everything that has happened, I do’nt think that makes any sense to Rory end up with Jess. Rory rejected Jess twice, once to stay with Dean and the other with Logan. I don’t think they’re end game, it would’nt show any improvement for Jess and there’s no time to develop something again for them. Jess seems to be somebody there to push Rory and help her with personal growth, that’s what I think Milo meanning with “the ball”.

    Both #teamdean and #teamjess are faded and their time’s gone. What AMP may do is take back Logan and Rory’s relationship and make it work, showing how Rory is now professionaly satisfied and is ready to marry him. If Rory is going to end up with one of them, I would bet Logan and all clues point it.

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  • August 25, 2016 at 8:58 pm
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    While the characters are frozen in time [at least in our minds till we see them again] it’s unrealistic to believe after nine years that all three guys are still available and it would not be surprising if none of them were still on the market. Of course writers have a way of making the improbable seem quite reasonable so I’m sure they will rekindle some old flames. My pref is still team noone if these are the only three choices.

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    • November 15, 2016 at 10:40 pm
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      I would put money on Dean married with kids! However, I think both Jess and Logan might still be single (however recently).

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  • August 25, 2016 at 11:00 pm
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    I think of Jess as that bad-boy-come-good, storybook, movie love you have before you find the “One”. He’s perfect for you except that it just will never work out for whatever reason. They were meant to be in your life, break you, make you grow. And you still have a connection with them, but making a life together sort of ends those sparks. I personally feel Rory and Jess, had a better banter/relationship when they weren’t together. All that lovely romantic angst and pining was what made their relationship so desirable and enviable. To be wanted, to want something you can’t have/ It was a relationship based on crossing some boundaries, which is fun. Breaking the rules IS fun. But that adrenaline pumping, heart thumping, head swirling romance/courtship does not always translate to a good partnership in the long run.

    LoganRory was a very realistic depiction of a college/serious relationship. That playboy-finds-girl-he’s-willing-to-change-for does happen, trust me. And it’s believable. His character was everything Rory needed. And Rory was what he needed. They supported each other when the other was at their most vulnerable. He went to Lorelei to win her back. He got his shizz together after having a complete breakdown after losing that money. Logan wasn’t perfect, but neither is Rory but in the end I think they were the best together.

    Only thing that bugs me is the whole Rory kissing Jess while still together with Logan thing. I mean she forgave him to a point for his activities when HE thought they were broken up. But when she kisses Jess, they weren’t even remotely, even on her side, broken up.

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  • August 28, 2016 at 8:35 am
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    Honestly? I don’t think she’s good enough for him. People keep going on and on in the show about how wonderful she is… but she really isn’t that great. She’s a bit spoiled and bratty.

    The whole dropping out of Yale thing? And the Yacht?

    Actually, why go that far? She had an affair with a married man, for heavens’ sake.

    And, unlike Jess, this was not something she started out with and moved past. This was something that developed with time.

    But, in the end, I think the core is sound (She used to be a really good kid, once upon a time, after all) and I think he can do a lot to straighten her out just like she straightened him out. He did it when she left Yale, I think he can do it on a more permanent basis.

    She needs him… I’m not sure that isn’t ever so slightly appealing. You know? Someone you respect and admire and find attractive… needing you?

    So, would he choose her? Maybe, yeah.

    At any rate, I hope so.

    #TeamJess

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  • August 28, 2016 at 12:38 pm
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    Rory needs Jess like a dog needs fleas

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  • August 29, 2016 at 2:30 pm
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    I think Rory and Jess, if they have stayed on the path that we left both of them on, would be the best match. I really, really hate the idea of her ending up with Logan. I would be incredibly sad if that happens. My inner teenage self would love it is she ended up with Jess but my 26 year old self, could also get on board with a potentially new, solid love interest and also, I would be totally fine with her being single.

    I actually think the question of wheither or not Jess would want to be with Rory is intresting. If he has worked hard to be a better person and really do something with his life and Rory is still something similar to the selfish brat that she was in the ltter seasons, I would say he could do better!

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  • October 1, 2016 at 11:55 am
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    Who ever writes these clearly don’t care for Jess.

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  • October 26, 2016 at 4:36 am
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    Jess is damaged and deep down he’s had to go through so much. Yes he treated Rory like dirt when they were together and she deserved better, but he was a teenager who came from a life surrounded by nothing but disappointment and hurt and of which he was treated like dirt. Of course he didn’t know how to treat Luke nor Rory with respect. No one had ever treated him with respect. He couldn’t trust his own mother. How was he expected to trust anyone else or himself for that matter? Not everyone has the privilege of being born into a stable and positive environment with positive role models to teach them the basics such as respect. It was sure to take him some time to learn how to trust and treat people respectively because he had to learn that himsd, and that he did. He developed into an amazing person with very little guidance nor direction from anyone else. Thank goodness he met Luke and Rory just at the right time. Jess leaving without saying goodbye was horrible but I honestly think he believed he was doing the right thing by Rory and everyone else by leaving.
    I’d love to see Rory and Jess end up together as they bring out the best in each other. She pushed him to be better and do more and he pushed her to go back to Yale, lf which she wouldn’t have dropped out if it weren’t for Logan’s horrible interfering parents.

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