How "Gilmore Girls" Should’ve Ended, The Rory Gilmore’s Boyfriend Edition

“Ugh, Logan.”

Chelsea Marshall: I think it’s best that Rory ends up by herself for that time because you know ~female empowerment~, but Jess is the best.
Keely Flaherty: Strong agree.
Ann Marie Alcantara: Yes.
Chelsea: And most adorable and, like, he was a doofus, but he was 16!
Sami Main: Jess was a much better option for her at the end of the show than he was when they were actually dating, to be fair.
Keely: I think it was good that they didn’t end up together, because they definitely needed to go down their own paths, but the core of their relationship always stayed the same.
Sami: HE WROTE A BOOK. HE WAS DOING THINGS WITH HIS LIFE.
Matthew Perpetua: Jess is definitely the coolest, and probably the smartest.
Keely: Like when he showed up when she was taking a break from Yale like, “I know you better than anyone, what are you doing?!”
Ann Marie: Yeah, if he didn’t like something, he made it clear.
Chelsea: He had the stupid teenage things that get in the way of being a decent human, but there was always a decent human underneath. Because he was smart and believed in Rory.
Sami: He had some crappy childhood moments, and Rory had, like, pretty idyllic ones.

Matthew: He’s not the most fun, though. Logan is obviously the most fun.
Chelsea: That’s ‘cause Logan was a rich brat.
Keely: Ugh, Logan. Also, Logan was like a budding alcoholic.
Matthew: I feel like Logan is interesting with Rory because he is so totally at ease with his privileged background and embraces it, and they meet at a point where she’s only kinda tentatively embracing that part of her family.
Sami: But Logan was also a gambler of LIFE. He had money, but he wasn’t mature and hadn’t really learned anything about LIVING and expected her to, like, go along with his dumb ride.
Ann Marie: I still remember his speech about “not wanting the path his dad chose for him.”
Matthew: Like, I think people often pair up with someone who complements the things they are interested in or paths they want to explore, and Jess was ideal in high school because he was invested in writing and reading like her but was also a REBEL in a way Rory wouldn’t allow herself to be. Logan kinda does that too; he pushes her to get out of her shell, and I think that character is always looking for someone with a stronger personality who pushes her to be more active. And that includes her mom and Paris.
Chelsea: I also think that when he got older and more stable, he’s sooo ideal.
Megan Palone: Jess was the one who came and shook her back into reality after she left Yale; he was the one who knew exactly what she needed at that moment, whereas Logan was a total douche at that point.
Keely: Such a douche.

Chelsea: The thing with Jess is that he pushed her without ever diminishing who she was, whereas it never felt like Logan saw Rory.
Keely: And he pushed her into things she liked, things that weren’t bad for her.
Matthew: Yeah, I bet IRL, Jess and Rory would keep coming into each other’s orbits but never really working even if they tried. Just like her mother and father!
Keely: That’s a suuuper interesting parallel.
Chelsea: Jess is way better than Christopher though!
Keely: ‘Cause I kinda always saw Christopher as Dean.
Chelsea: Because they’re both idiots.
Matthew: And I think their relationship would be doomed because Jess has this vision of Rory that’s stuck in time.
Chelsea: I actually don’t think so.
Keely: Strong disagree.
Megan: I feel like even when Christopher “grew up” though, he never really grew up, but Jess did.
Chelsea: Jess wanted Rory to grow and understood her soul at the same time. Jess didn’t go find another Rory, like Christopher goes and finds another family to have a do-over.
Matthew: Well, we don’t really see THAT much of “grown-up” Jess, which makes me think that even though I could see them orbiting around for a little while, they’d get it together at some point.
Keely: I think Jess was the only one who saw Rory down and out, wasn’t disappointed, and didn’t see her differently. He just wanted to help.
Sami: Jess kind of let her ~go~. Chris kept coming back to Lorelai to ruin everything.
Megan: Right, yes, Sami!
Ann Marie: Yeah, Sami! He let her do her.
Chelsea: Jess is magnificent. Can we just stop and remember how Jess went to his mom’s husband’s bachelor party, and he started READING in a strip club?
Megan: And yes, Chris is awful.
Ann Marie: Chris is the worst. THE WORST.

Matthew: I think Jess and Christopher are only parallel in that their relationships with Rory and Lorelai always seem unfinished and it’s this constant “what if?” and “maybe this time.”
Chelsea: But I think Jess and Rory will eventually end up together, but there’s too much shit with Christopher to end up with Lorelai.
Sami: Dean, Jess, and Logan are three facets of Christopher’s overall personality.
Matthew: I think you’re right, Sami.
Sami: The puppydog first love floppy hair (Dean), the rebel bad boy (Jess), who then reforms into a rich, entitled butthole (Logan).
Megan: Oh yes yes.
Chelsea: Yeah.
Ann Marie: OMG yessss.
Matthew: I think you could go from there and just extrapolate that Rory is always trying to create her idealized vision of her parents in her place, a version that doesn’t break up.
Ann Marie: Yeah! A little less falling head over heels.
Matthew: Don’t you think she would learn to gravitate more to a Luke type, or would that have to be more in her thirties, like her mom did?
Sami: But Jess is a Baby Luke. (Which would make them all related but whatever.)
Matthew: The best elements of Jess are Luke.
Sami: Rory could’ve been dating Jess at the end, even when she went on her press tour.
Ann Marie: Yeah! Like he would be OK with long distance ‘cause they are the type of people who could do their own thing but still function well together.
Chelsea: YES, I think that’s why I love Jess so much.
Keely: Jess MARRYano haha bye.
Chelsea: He wasn’t needy, and they seemed like a relationship that if they were more mature would actually be really fulfilling
Matthew: I guess my thing is that I just don’t see Rory moving backward that much in her life, especially as she goes off on this adventurous career. I think she’d just end up with new people, probably better people.
Chelsea: I think Jess is the only one who doesn’t feel backward though because of how much he grew and she grew and they could grow together like two little baby Groots side by side.
Sami: I do see the point of, like, that’s WHY the show ended with her not with a guy, because that’s not the point of being an independent grown-up. She’s awesome on her own and gets to have an amazing life REGARDLESS of who she’s with. B U T if she had to be with someone at the end, I would prefer Jess.
Keely: Ditto.

Matthew: But wait. What do you think of MARTY?
Ann Marie: NO. Marty aka “I lied to my awesome girlfriend and still loved Rory after so many years.”
Chelsea: Marty sucks. Marty says he’s in the friend zone. He’s the poster boy for friend zone.
Megan: OK, I love Marty, but the problem with him was that he was never a fully realized character and then they just made him suck at the end. Marty would have been a great rebound early on.
Matthew: My memory of Season 7 is foggy but didn’t he hook up with Kristin Ritter’s character? Krysten, sorry.
Megan: Yeah — Marty and Krysten Ritter were dating, and he lied about knowing Rory.
Sami: So Marty lied, Logan lied kind of/basically, Dean lied TO HIS OWN WIFE, but Jess never LIED. As an adult.
Megan: Dean lied and CHEATED, and Logan basically cheated too.
Ann Marie: Yeah HE DID, even though he had that stupid excuse.
Chelsea: OK. But how long were they not speaking?
Sami: It felt like…a few weeks? Couple weeks? Maybe a month and a half?
Chelsea: Like, if I just flat-out stopped speaking to someone for months…
Sami: RIGHT, but like, he expected her to be OK with it and didn’t tell her ANYTHING because he felt guilty.
Chelsea: Yeah, he should’ve told her, but I think he honestly thought they broke up.
Sami: While I agree it DID seem to him like they were apart, to expect her not to be upset when the info was sprung on her is crazy.

Matthew: Would any of you date Logan if you met him and he aggressively wooed you, like he did with Rory? I feel like his flirtation style is a bit MUCH.
Ann Marie: No.
Matthew: Logan doesn’t seem to get boundaries.
Megan: Yes, Logan is too much. No, would not date.
Sami: It was too much, but after seeing Rory’s process through it, I’m thinking I’d do something similar? It was far too over the top. It is nice, however, to be desired. But dang.
Matthew: All three of those guys are WAY into big romantic gestures.
Chelsea: What did Jess do that was over the top?
Matthew: He was maybe less over the top, more of a “I wrote notes in this book for you,” but still really romantic, and he put her on a pedestal.
Sami: Jess did zero over-the-top things. He was all under the top (hey-oooo) (but also was crappy in the beginning when he was moody).
Chelsea: OMG the notes in the book is so romantic.
Sami: To me that’s not AT ALL on the same level as BUILDING A CAR or all the expensive things Logan did.
Ann Marie: Jess never did anything over the top? His big gesture was maybe driving all the way to Stars Hollow to say “I love you” to Rory.
Matthew: I can’t really remember, but did Logan ever do any romantic thing that he didn’t need MONEY for?
Chelsea: EXACTLY. I don’t think so. I feel like he went to the store and was like, “I HAVE MILLIONS; LET ME SHOW THIS LADY I HAVE MILLIONS.”

Matthew: I think Lorelai liked Dean best?
Chelsea: That’s ‘cause he was safe.
Sami: And he changed the water bottle.
Matthew: And he was never a MASSIVE DOUCHE to her, like Jess.
Sami: She did NOT like him near the end tho when HE CHEATED ON HIS WIFE.
Chelsea: A giant shitbag.
Sami: IN ORDER TO TAKE RORY’S VIRGINITY. “Take.” But still.
Chelsea: It felt that way, like he was “taking” something even though obviously that’s not anything for taking or whatever. But because he cheated on his wife and it was just all really weird, it felt really selfish of him in all regards to make that a shitty experience.
Sami: In the feminist sense, why do we refer to a woman’s virginity as something that can belong to a man?
Chelsea: Totally! And remember how shitty he was to his wife? Granted, it made zero sense why she didn’t work when she wasn’t in school or have kids or anything, but she tried so hard and Dean was just a giant shitbag. I’m really enjoying calling him that.
Ann Marie: She tried to cook for him!
Chelsea: Yeah! And dress up! And just talk to him!
Sami: Oh my god, Dean and Lindsey got married too young just like the big WHAT IF of Lorelai and Christopher.
Matthew: Dean is just such a “guy you knew in high school” and I really appreciate them making him a huge fuckup.
Chelsea: Dean was just so basic. Basic Dean.

16. (A Parisian aside:)


Matthew: I just want to put it out there that I find femslash about Rory and Paris VERY CONVINCING.
Chelsea: (I don’t know what femslash is.) But I hated Paris, always.
Sami: (It’s fanfic that’s like two girls in a relationship.)
Matthew: Strong disagree! I love Paris so much soooo much. Paris is 10 billion times better than Jess. Scientific fact.
Megan: God I love Paris. Not better than Jess for Rory, but def a better character.
Sami: Love her as a character by the end of things, but I don’t think she and Rory should’ve been a thing.
Chelsea: She’s a good character but she’s… I guess I don’t really love friends that you couldn’t trust to be in your corner.
Matthew: To be really honest, the only male characters on Gilmore Girls who I really like a lot are Luke and Richard.
Ann Marie: Yeah true, Chelsea.
Keely: In the beginning of the show, Paris was the worst.
Ann Marie: She was so mean! But then she had some really soft moments.
Chelsea: I guess I identify with Rory a lot, and she just would never fuck anyone over intentionally but Paris would.

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