The ULTRA important Gilmore Girls post I’ve wanted to write forever: Rory + Jess ALWAYS

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Yes, I really am writing an entire blog post on a show that ended seven years ago and which guy one of the characters should’ve ended up with. Go ahead and mock me…I don’t even care.

OKAY. I realize this post is many years late. I realize that many people have stopped caring…or never cared in the first place.

But I also know many people still do care. (Evidence: The gobs of FB conversations about this very topic I’ve been involved in just recently–none of which I even instigated!) I even know some MEN who care. Care about what, you ask?

Gilmore Girls.

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Yeah, yeah, I know it ended several years ago. In 2007, okay?!

First, let me say I didn’t actually watch Gilmore Girls all that much when it originally aired. But then I randomly started watching reruns with a friend and got slightly massively addicted. Who cares that no single town in the real world could ever be so full of interesting, eclectic and witty characters as Stars Hollow? Who cares? Stars Hollow is awesome and Lorelei and Luke are the cutest couple ever and the writing is so ridiculously whip-smart. I LOVE IT!

I love the dialogue, especially. Seriously, they throw out awesome and many times obscure pop culture references with more generosity than any candy-throwing person on a parade ever. (What is it with people being stingy throwing candy during parades? Two or three tootsie rolls every ten feet? No, that’s just wrong. You chuck it by the hand full or you don’t chuck it at all.)

That’s not to say I don’t have some gripes with the show. I mean, let’s face it: Rory turned pretty idiotic in the latter seasons. Luke and Lorelei’s issues in season 6 smelled very jump-the-sharky to me. The writing in the last season suffered greatly with the loss of Amy Sherman-Palladino.

But my love overshadows those issues. There’s only one outstanding issue I have that I still haven’t gotten over. And I don’t think I ever will. Not until they create a Gilmore Girls movie and right this wrong. This wrong being:

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Not that Jess himself is wrong. Oh no, he’s so SO right.

And he and Rory should’ve ended up together!

They just should’ve. I say it every single time I watch GG (to the point that my sister rolls her eyes)…but I really can’t get over it. And so I finally had to write the post I’ve been dying to write for years.

Dean

To start with, a quick look at Rory’s other two loves:

DEAN: Now, he’s a chump, yes, but let’s cut first-season Dean a little slack. He was cool back then. He liked the same books and movies Rory liked and they actually had interesting conversations. And he built her a car, which is pretty nice. My theory: I think the writers purposely dumbed him down mid-season two and beyond in order to make way for Jess. Dean suddenly got stale and boring. By the bid-on-a-basket episode in S2, I was so over him. And by S4, I just wanted to deck him every time he came on the screen.

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LOGAN: I know so many girls who love Logan. And look, he’s okay. He’s cute, sure, and he’s pretty funny. But he just never did it for me. He was a little too whiney. A little too preppy. And while I’m glad he finally got out from under his father’s thumb and started that internet company, I think Rory was right to turn down his proposal.

Sidenote: Some people might also consider Tristan (Chad Michael Murray—dude, remember him?) and Marty as Rory-love interests as well. But I’m trying to keep this post from getting too crazy long, so they got bumped…

Why Jess is the best and why he and Rory totally belong together!

Now lest I go on forever and ever and blow this word count through the roof and make all the blogging authorities angry, I’m limiting myself to 15 reasons. Here goes…

1) Rory skips school to go see Jess in NYC. That was so huge and significant and she even misses her mom’s graduation and I love it. And Rory apologizing and crying and agonizing to her mom at the end of that episode is pretty much my favorite mother-daughter moment of the whole series.

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I love Rory’s response. “Maybe later.”

2) He’s Rory’s intellectual equal. They actually have fun stuff to talk about. They argue in a good way. He gets Rory in a way none of the others ever do.

3) He’s a writer. Bonus points!

4) He’s the bad boy who’s really not so much of a bad boy. He just has a hard past and he needs someone to believe in him.

5) He tells Rory he loves her…and then literally runs away! What girl in her right mind doesn’t run after that guy? What girl? (And no, clearly this would not be nearly as cute if he was, say, 40. But he’s still young enough that it falls under the “awww” category.)

6) He’s Luke’s nephew. So clearly he has good genes.

7) Chemistry. Rory and Jess ooze chemistry in a way Rory and Dean and Rory and Logan never do. It’s so obvious!!

8) He eventually finds his way…it just takes him a little longer, that’s all. When he comes back in the latter seasons, he’s finally got it together and knows what he wants and he goes after it in an awesome way. I don’t understand why Rory doesn’t drop Logan right then. COME ON. (Honestly, maybe Jess is TOO good for late-seasons-Rory, now that I’m thinking about this.)

9) He gets a black eye…after being beaked by a swan. Sympathy points!

10) He actually reads that self-help book Luke gives him about finding love. Cute points!

11) He always has the best things to say. I dare either Dean or Logan to be half as brilliant or funny…

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Yeah. For real.

12) He brings Rory food in that one S2 episode. Specifically, he brings her French fries.

13) He pulls awesome pranks. Stealing all the school’s baseballs. Stealing Pierpont the garden gnome. Creating a dead body outline in chalk outside the grocery store.

14) He keeps coming back for Rory. At the end of S2. In S4. In S6. (Okay, so he wasn’t really coming back “for” Rory in S6…he mainly just wanted to show her his book and tell her he couldn’t have done it without her. But still.)

15) He takes risks. And not dumb Life-or-Death-Brigade risks like Logan. But he actually risks his heart. Not only on Rory…but he takes a risk when he decides to trust Luke. When he goes off to find his father. When he writes his book. When he and his friends open that press. And I like that about him.

Phew. Okay, FINALLY got all that off my chest. I could probably come up with 75 more reasons, but then people might start to question my grasp on reality. So instead, I’m throwing it out to you:

If you watched Gilmore Girls, which of Rory’s boyfriends did you like most?

(I’m not even going to ask about Lorelei’s…because obviously the answer is Luke. Obviously. Although, I have to say, I have a major soft spot for Max…)

p.s. I realize probably 80-90% of Gilmore Girls viewers disagree with me on Jess. That’s okay. In fact, I would very much enjoy arguing the point at length. So go ahead and disagree in the comments! And if you have never watched Gilmore Girls and you’re actually still reading at this point a) wow, thanks! but b) probably your time would be better spent diving into the wonderfulness that is Stars Hollow!

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    Comments 50

    1. I love Gilmore Girls. I have issues with it, too, mainly how both Rory and Lorelei can be so smart at times and then do such incredibly stupid things! Also, I don’t care for the language and some of the content. But I love the characters and Stars Hollow. Seriously, I want to live there. Kirk is one of my favorite fictional characters ever. =)

      You make good points about Jess. And in general, I’d have to agree with you. Of course I loved Dean at the beginning. He was sweet and adorable, and when Jess came on the scene I didn’t like him because he was making Rory forget about Dean. But I eventually came to like Jess, after he got out of the worst of his “bad boy” phase. =) I didn’t like it when Dean came back into Rory’s life and all of the mess that happened after that…Dean had his place in the beginning, but I didn’t want him around anymore! And Logan: ew. I never, ever liked him and I couldn’t figure out why other girls did! He’s such a slimey, arrogant jerk and while he did improve later on, I still can’t stand him. When Jess came back later, I desperately wanted Rory to ditch Logan and get back with Jess. =) So even though he didn’t make the best first impression on me, I think of the three, I probably like Jess the best. And I definitely agree that he and Rory would have been perfect for each other later on.

      Random thoughts about Jess: I love it when he and Luke are reading the self-help books. Hilarious! Also, I loved it when Rory (and who else was with her? Lorelei?) egged his old car with deviled eggs. =) And while I didn’t appreciate his pranks at first, they were pretty great. The chalk body outline was priceless.

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        Haha, you’re right, for being two smart girls, Rory and Lorelei do make some dumb decisions. The one I had the most issue with was when Rory dropped out of Yale. I was like, I can understand all sorts of ridiculousness, but that was over the top.

        Yeah, I actually felt bad for Dean’s character…he started over pretty great but just slowly morphed into this kinda dumb and worse, overbearing, guy. And yeah, the whole thing with Dean’s marriage and Rory was soooo bad. And I’m glad I’m not the only who never really liked Logan. You’re right…he improved. But he never quite lost that ick factor for me.

        And yes, Luke and Jess reading the self-help books is one of my favorite things EVER.

    2. It’s only just occured to me that commenting here makes more sense than commenting on facebook.

      Yeah, Dean was okay. He was just kind of overly sweet to me. And super jealous in a not-at-all attractive way. I mean, the way he reacted to all that Tristan stuff? Yeah…

      I seriously don’t know how Rory turned down Jess’ offer to run away with him. For DEAN. Whaaaaaat?

      And I liked Logan. But you’re right, they never had the same chemistry. (Do you think this was the writers’ intention? Or just the fact that Alexis Bledel and Milo Ventimiglia actually dated for awhile and this just came out in their acting…?)

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        Oh yeah, when Dean turned super-jealous, that’s when he lost me once and for all. I kept trying to give him the benefit of the doubt midway through season two…but when he got overbearing, he and I were done. LOL!

        I don’t know how Rory turned Jess down either! I remember watching that episode for the first time and getting soooooo mad…

        I’ve thought many times that possibly the reason Rory and Jess worked so well on the show is because they were dating in real life. They had the best chemistry of any couple on the show, for sure.

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    3. First, I’ve only watched a few reruns of the show, so I’m not qualified to chime in. But I’m throwing out my opinion anyway based on the pictures and info you gave (I do that a lot).
      1. Logan? Eww. Just Eww.
      2. Dean? Maybe good for Buffy the Vampire Slayer or something.
      3. Jess? Uh, yeah!! You’re telling me out of these three, Rory did NOT end up with the hunkalicious cutey?? That just seems really wrong. 🙁

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        Well, in my imagination, she did finally, eventually end up with Jess. LOL! The thing with Jess is, he had a lot of issues early on. He needed to sort some things out…figure out what he wanted in life…you know, all that stuff. So it makes sense that they didn’t work out initially. But later in life…HELLO perfect match!

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        Oh Jess, I think you’ll love it. It’s so fun. My one warning: When I first started watching it, I kept thinking, why is every single character on this show witty and funny and pop-culture-smart? It seemed a bit unbelievable at first. But I got over that quickly because I loved the wit and humor and pop-culture-smartness. 🙂

    4. I agree!! I always wanted her to stay with bad boy Jess, who totally understood her. What is better than having a guy to discuss books with? A guy who understands your obsession to visit a bookstore every time you visit a new city.
      I NEVER liked Logan. He was part of a life that Rory really never wanted, so why did she date a guy who enjoyed the free ride life? He was snotty and cheated on her a number of times. Rory should have left him.
      I really believed when she went to visit Jess in New York because his small press book came out that she would start dating him. Too bad they didn’t.

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        I was with you, Kelly, on when Rory went to that book launch thingy to see Jess that they’d get back together. It would’ve been perfect…

        And you make good points about Logan. He WAS a part of a life she never wanted…I can understand why the writers had her with him for awhile…but stretching it out over several seasons was too much.

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        It’s a pretty fun one, Pat. Super witty…this is going to make me sound like a total nerd, but I love watching it and seeing how many of the obscure pop culture references I can pinpoint in an episode. And now that I’ve just admitted that, I feel slightly embarrassed…

    5. Hmmm, I probably agree with you. I do know I got very upset at the ending (not that she turned down Logan, but how she ended up with no one!). I didn’t like Rory in later seasons. And yeah, Dean. Grrrr. What happened mid-show just made me so mad. Like, really? Why would you cheat on a girl named Lindsay?! (Seriously, though, thought that was so strange and contrived…and so not Rory. Hated it.)

      LOL, I do remember my husband watching the show occasionally and referring to Dean as the guy with “horrible hair.”

      And yeah, I liked Jess. I could probably let you convince me he and Rory belong together…that is, first-few-seasons Rory and late-seasons Jess. 😉

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        But see, I like that Rory ended up with no one. I feel like that was more true to her character at that point in her life. She had just graduated college and was all “I’m finally gonna be Christiane Amanpour (sp?)”…it felt right to me.

        Although, in my imagination, she still eventually ends up with Jess. And yes, early seasons Rory and late seasons Jess is a good pairing. Although, let’s be honest, I liked early seasons Jess too. Even in all his screw-ups, I loved him. I can’t help it…I’m always a sucker for the wounded, faulty character with a good heart who just needs someone to believe in him…lol!

    6. Ok – I LOVE Gilmore Girls so thanks for this post! I never watched it when it was on for real (I missed pretty much everything that started in the early 2000’s since my kids were little then) but I caught up later on and own every season on DVD. I was always way more interested in Lorelai’s love life because she was closer to my age (love, love, love, Luke, not so much Christopher). Saying that though, I was a Dean fan. I always thought Jess had too much baggage and wasn’t good for Rory in the beginning. But, you make a compelling case. I can see how she could end up with him in the long run. He really is more of a match for her intellectually and socially.

      I may have to break out my DVD’s and do a Gilmore Girls marathon and relive the goodness!

      PS – do you know that Lauren Graham wrote a book – I just read it – it’s called Someday, Someday, Maybe and it is lovely. 🙂

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        Yes, I read Graham’s book!! I adored it…absolutely adored it. Her writing, the voice…I sooo hope there’s a sequel.

        Actually, I’m with you on being more interested in Lorelei’s relationship. But her’s was always so clear with Luke as the obvious choice. (Although, as I’ve rewatched the early seasons, I really did like Max too. He was witty and smart and fun. I never really cared all that much for Chris.) Yes, Jess had a lot of baggage…but to me, that made him interesting and more fun to watch versus Dean and Logan. Granted, Logan had baggage too…but he was just toooo preppy for me!

        And mostly, I just love that I’m having so many serious conversations about this with people today. Between here and FB, it’s been fun..lol!

        1. I’m finding I do this alot- talk about fictional characters like they are real. But I figure that is just a testament to the writers and actors that they can create such believable characters…not that I have any kind of mental issues….:)

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    7. Ahhh. I’ve never watched Gilmore Girls, but then again, I don’t watch much T.V. except classic movies and oldies shows. (No cracks, okay? LOL) Although—I know you won’t believe it, but I’ve become a fan of The Blacklist. The new high energy drama with James Spader on Monday nights. A bit of a stretch for this Heartfelt, Homespun Fiction gal. Go figure! haha

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    8. I only watched one or two episodes of this, but everyone around me was hooked! Now you’re snagging me:) I know it was a great show, so guess I’m gonna have to check it out on iTunes.

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    9. Never watched Gilmore Girls but my cousin watches the show and I’m pretty sure she liked it. It sounds good, which may not bode well for me since – hello! – this might mean I finally jump on board and give S1 a try. As if I don’t already fangirl over enough television shows. 😉

      Once again another fantastic post, Melissa! Love it.

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        Haha, yeah, Rissi…once you dive in you might be completely hooked. I really love it. It’s a great mother-daughter show. Funny thing is, I would never want a mother-daughter relationship like what’s on the show. I love that my mom was my MOM growing up, not my best friend. Now I consider her one of my best friends ever…but as a kid, I needed a parent more than I needed a friend. So it’s funny…as much as I love the Lorelei/Rory relationship when I watch GG, it often leaves me grateful my life looked quite a bit different.

        But yeah, I’m almost as fangirl about this show as Sherlock or 24. Almost. 🙂 (Man, just mentioning Sherlock, 24 and GG in the same comment makes me realize how varied my TV tastes are.)

    10. So glad someone else sees how perfect they would be together. My fantasy was always at Rory would come back from her year with the presidential campaign, having met and got back together with Jess at some point during it. He would have been really good at arguing politics with her and still be able to quiet her with a kiss!! Isn’t it great that sometimes we can carry on with a programme and make it even better….

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    11. Ok, you’re right…this post is so long overdue!

      I got hooked on Gilmore Girls while recovering from thyroid surgery. My oldest son, who is a romantic and closet chick flick watcher, started watching GG with me. He even bought me a season on DVD because we couldn’t find it online.

      I thought Dean was a bit of a whiner and then after he cheated on his wife…not happy about that.

      Jess, sweet misunderstood break my heart Jess…LOVE how he overcame his past to be his own person. He added sizzle to Rory’s vanilla life. He challenged her.

      Logan…I liked him a lot, and call me cheesy, but I loved that he called her Ace. However, he suffered from RBS…Rich Boy Syndrome and Rory was never good enough for him, despite her family’s reputation.

      Now I want to binge watch GG this weekend while working on taxes…yes, I led an incredibly glamorous life.

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        Binge-watch!! That’s never a bad choice.

        I agree that Jess challenged Rory. Jess is just the best, that’s all there is to it. I’m amazed today at how many people also like him. I always thought I was one of the only ones.

        You and Katie Ganshert should get together, Lisa. She likes Logan too.

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    12. I do not concur, my good friend. I LOVED Rory + Logan. But you already know this. 😉

      Jess treats Rory like absolute BUTT (yes, I said butt) in the early seasons. I mean, he was RIDICULOUSLY rude to Rory. And rude to Lorelai, which earned him no points with me. I will admit, he redeemed himself in the later season. Not to the point where I was rooting for him and Rory, but enough that he earned a soft spot in my heart.

      And maybe this says something really dysfunctional about me….but I find the whole womanizer-who-completely-falls-for-ONE-girl romantic plot a very swoon-worthy one. And that’s what happened with Logan. He was not about to settle down and go fall in love. Yet Rory completely stole his heart.

      Oh, and also. Logan is number 2, too.

      In my happy place, I imagine one more GG season, in which Logan and Rory live happily ever after.

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        The Jess talking with only one side of his mouth convo on FB earlier this morning is possibly one of my favorite FB conversations ever.

        The thing with Jess is, yes, he’s a mess in the early seasons and yeah he doesn’t treat Rory all that wonderfully all the time BUT sometimes he’s ridiculously sweet. And you can tell he wants to be better, he’s just so tormented by angst that he doesn’t know how! And he’s been so hurt…and he just needs someone to show him the way…and Luke does that…and…and…he’s GREAT! LOL…

        But I know you love Logan and so I will try, for the sake of friendship and open-mindedness, to see his cool side. He does throw a good party, I’ll say that for him…

    13. I have to agree with you. Though, I will say that Rory didn’t need Jess the way he was in high school. But that episode in later seasons where she goes to his book signing event. Yeah–THAT Jess was perfect for her. GG is my favorite show of all time, btw. 🙂

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        THAT Jess WAS perfect…finally a little more stable, calm, focused. I love the episode when he shows up at her grandparents house and tells her about his book, too. If Rory was any kind of smart, she would’ve thrown herself at him right then. 🙂

    14. I COMPLETELY agree with you! Jess is the best part of this show. While my husband accuses him of being bratty, I get the real Jess. He’s just misunderstood. Rory was an idiot not to dump Logan for him in S6. It drove me crazy. And I am so on board about a tv movie righting this wrong. And from what I’ve seen online the majority of GG fans agree that Jess was Rory’s soulmate.

      P.S. They dated in real life for like 7 years!

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        WOW I am so happy that so many people actually do like Jess. I’ve been hanging around the wrong GG viewers. 🙂

        And yes, I do wonder if part of the reason Rory and Jess were so perfect on-screen is because of their off-screen relationship.

    15. At the risk of infuriating everyone, here’s my rating for Rory’s guys.

      1. Logan
      2. Jess
      3. Marty
      4. Dean. I guess.

      Hear me out. Logan because, for everything Lorelai did to prevent it, Rory was born to extreme privilege. Their quirky house and town aside, the Gilmores were incredibly wealthy, while Rory’s own merits got her into Chilton and Yale (and Harvard, etc.), she was where she was because of the money she was born into. Logan helped her navigate that world, and understand its pitfalls. Despite his running once or twice from Rory’s super intense tendency to get SUPER-ATTACHED-SUPER-FAST — he came back and came to her aid several times, both professionally and personally. Beyond that, his confidence was sort of dreamy, and that he was always trying to whisk her away to Paris was also dreamy. And that he called her Ace. Because she was an Ace reporter. I loved that (my Journalism major’s heart exploded).

      Jess. Ah, Jess. I remember I was at a friends house, and we were channel surfing when suddenly we paused on his FACE, and that evening started what would become a 5-season television addiction. I think you’re right about the chemistry, but that’s just because they were dating IRL. But I will say, I’d never imagined what great TV kisses looked like until I saw Jess and Rory — the good times.

      Marty. What a cutie. Poor Marty. Poor wrong-place-wrong-time Marty. He, I think, represented where Rory came FROM. Not where she was going. He was smart, but insecure, and Rory didn’t need anymore Deans. She needed someone who was confident and who wasn’t going to hold her back.

      Dean. Ah Gad. DEAN. He reminds me of my first boyfriend Kurt (name changed for anonymity). Super cute. Super satisfied to become the town grocer/carpenter guy. WHICH ISN’T TO SAY THAT IT’S BAD. I’m married to a carpenter now, and he’s awesome at what he does. BUT. If I’d stayed with Kurt, I would never have left home for college, or moved to SF for work. I would have constantly been afraid of hurting his feelings with my ambition. I’d have never discovered ME. And, because this isn’t about me, in the end, Dean became whiny and selfish, and turned Rory’s “first time” into an affair with a married man.

      That’s my story and I’m stickin to it.

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          Even though I disagree about Logan (I want to like him more…I do…he just doesn’t do it for me!) I love your well-thought-out justification for all of this. 🙂

          And I love that you gave Marty some screen time here. I felt bad for him too. He was kinda Dean 2.0…but a much less overbearing and annoying Dean. I remember thinking as I watched season 5 that if Marty would just man up a bit, he might actually have a chance with her.

          As I’ve thought about this quite a bit today (so many fun conversations about SUCH an important topic…lol!) I’ve more and more started to think that Logan was Rory’s version of Christopher. In many ways a good and seemingly fitting match…but she needed someone a little more out of the box–someone with a different perspective on life than her. For Lorelei, that was Luke. For Rory…it could’ve been Jess!! 🙂

      1. I also loved Marty very much. In my opinion if Rory wasn’t going to end up with Jess, she should’ve ended up with Marty. So quirky and witty (and cute!)

    16. I really enjoyed Gilmore Girls. Did not realize how old it was. Frankly Lorelai has too many issues in her love life hence the daughter does the same. I never really liked the idea of Luke Danes marrying Lorelai. Was very disappointed. I found him too common and frankly a little dumb. And over possessive. Seriously she should have stayed with Rory’ s dad. He was witty. Rory should have married Logan. He totally looked out for her. Dean. Not smart enough. Too Hicksville. Jess smart but not classy enough. Could not see a bright future with him. I really think a new sequel would be good

    17. Firstly, obviously Rory couldn’t end up with Dean. Honestly, I don’t think it was Dean who got dumber but Rory who got smarter. She went to Chilton, she worked hard, was exposed to more of the world and as a result became disillusioned with Dean. He was a great first boyfriend but they never really had anything to connect them. Neither common interests or direction in life.
      With Logan I think Rory was living out a fantasy. Having grown up without money, the world of her grandparents and Chilton’s rich had always fascinated her. At Yale she was looking for new experiences and some fun and she explored that world. Logan was a great guy and they both loved each other. But at the end, their lives were too different. She realised that she didn’t want to fit into that world. That’s why she refused his proposal.
      Jess was the only one she connected with intellectually. He was the only one who could potentially live a life with Rory. Their only problem was that he was troubled but he sorts all of that out. So really, there is no reason why Jess and Rory should not be very happy together. Writing and travelling and talking about books with Rory’s child in tow.

    18. this is stupid,jess had a horrible attitude to Lorelai and was only nice because of rory who cheated on dean instead of leaving him rory didn’t deserve jess either in the later years because her character was so self centered she’s easily the worst character to me

    19. I totally agree!! I am rewatching the show and I am getting more frustrated by the minute because Jess is perfect for her! He gets her, he reads, he writes, he’s attractive! He’s just the best!

    20. Jess was objectively awful to Rory. He doesn’t get a free pass, because of his crappy childhood, and he certainly doesn’t for sexual assault. I disagree about the chemistry, sorry. I always thought Logan and Rory’s chemistry was far better. Rory was more drawn to the wealthy side of her family than fans like to admit. And as far as intellectually stimulating, she had that with Logan too. As a matter of fact, she told Lorelai that Logan was smarter than her. Let’s not pretend that Logan wasn’t well-read, just because he didn’t flaunt it. On Logan’s worst day, he’s still better than Jess just for the sheer fact he didn’t pressure her into sex, sexually assault her, and then blame HER. Love Milo, hate Jess.

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