‘Ship Wars: Gilmore Girls Rachael Berkey

Few things can cause a rift between my friends and me faster than a war – a ‘ship war, that is. We all have them – our absolutely favorite OTP (that’s One True Pair for those of you not in the know) – and there is nothing you can say that will change our minds.

I’m just going to tell you right now that this post will be full – and I mean full – of spoilers for Gilmore Girls. So if that bothers you, you should just skedaddle right now.

So here we go. This is the ‘ship war currently wrecking havoc on my twitter feed. Don’t worry. It’s all in good fun. I think.

I’ve written about her before so it’s probably no surprise that I have a special fondness for Rory Gilmore. She’s a total bookworm with a totally rad mom and a pretty stellar group of friends I kind of wish were mine too. And to top it off, over the course of seven seasons, she had a bevy of attractive boyfriends who complimented her in different ways.

Aside from, maybe, the question over who Doctor Who has loved/will love/does love, I cannot think of another ‘ship as contested as Rory and her paramours. I myself am a total Rogan fan.

Don’t stop reading just because you disagree with me. I will give them all fair treatment. For me though, the guy who complimented her best was Logan, her college sweetheart.

But let us go back to the beginning before I go into all the details of why I think Rory and Logan were best suited to each other. First, and longest, there was Dean.

deanandroryAh Dean. You were adorable in the beginning. The new boy in town. The mysterious and dreamy freshman with an eye for a girl constantly distracted by a book. If that doesn’t scream “perfect” to you, then clearly you do not read as much as I do. Dean was lovely and patient and kind. He took care of Rory and was a great first boyfriend, don’t get me wrong. And yes, the way their relationship ended the first time was crappy all around. He was exactly the kind of boyfriend that you get the feeling Lorelai wanted for her daughter.

JessandRoryThen there was Jess. He is the most hotly defended of Rory’s boyfriends by my friends. He was smart, totally bookish and rocked a leather jacket and bad boy demeanor well enough to attract the good girl and not fool Lorelai for a second. Plus, he was kith and kin to Luke, the resident father figure and all-around-good-guy in town. But he had an attitude and was dealing with his own baggage from the moment he showed up in town to the moment he climbed on bus and ran away.

And then there was Dean again. Yeah he came back. I scowl in the general direction of that entire musical montage and the bad decisions that were made all around.

Rory-and-Logan-gilmore-girls-951597_1494_1082And finally, there was Logan. Unlike her previous boyfriends, Logan was someone that her grandparents actually approved of but who made Lorelai’s skin crawl which was kind of fun to see. He perfectly represented everything that Rory’s mother had fled when she took her baby and ran at sixteen, and he had the smarts, polished manners, and general devil-may-care attitude to go along with it.
Rory’s beaus all come with pros and cons.

Dean is lovely and clearly cares about her deeply. Until he can’t control his jealousy (break up #1), can’t control his lust (makeup #1) and can’t handle Rory’s socioeconomic background (break up #2). Dean is flawed in multiple ways and the poor decisions he and Rory make over the years are actually somewhat realistic. They learn from them, and I like to think that they are probably both better (fictional) people for having had each other as first loves.

Jess is the first guy who seems to really challenge Rory. He forces her to step outside of her comfort zone in many, many ways, and he is understandably smitten and confused by her at the same time. But as I said previously, he has issues of his own that supersede a teenage romance (break up #1), and by the time he’s figured himself out and become a guy who understands himself, she’s in love with someone else. His strongest moments, in my opinion, are when he’s calling her on her irresponsible behavior and forces her to take steps to grow up too. (appearance #2) It’s kind of great.

What I think works best about Rory and Logan is that they actually challenge and force each other to grow in specific ways. Logan finds in Rory a girl who doesn’t just want him for his money, who won’t be a conquest and won’t be easily won. He’s forced to actually learn to have a real relationship with compromise and communication. On the flip side, Rory learns to navigate a relationship with someone who is socially, financially and intellectually on the same footing as she is – a situation she doesn’t find herself in with either Dean or Jess.

In the end, Rory ends up right where she belongs – at Luke’s Diner with her mother. She’s single again and about to set out on a grand adventure. As my friend Sarah said during my last battle of the ‘ship war on twitter, there is always the hope that Rory will go off to do her campaign journalism and will meet someone fabulous who totally deserves her and who she totally deserves.

Knowing what you do about her first three boyfriends, who would you hope she finds out there on the road?

Feature Image via Crushable; Dean Image; Jess Image; Logan Image

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  1. I’m saying Jess. Not the Jess from High School but the grown up, got his stuff together Jess. They always fit better than any of the others and once Jess is able to devote himself to her and not be focused on his teenage angst I think he is the best guy for her. They both just needed to grow up and have their own experiences first.

  2. I always felt like had Tristan been given the proper chance, he would have won out over all of the rest of them, in the end. Like the Sabrina/Harvey ending in Sabrina the Teenage Witch.

  3. It’s funny how many people think Rory belonged with Logan. But Logan was probably the worst boyfriend for her. He pushed her to feel free, and was the perfect person for her selfish college phase, but he never really gave her what she needed emotionally. He was as unstable for her as Jess was in a lot of ways, with the same neglectful parental issues. Dean was never her equal and as much as he put her on a pedestal, he resented her for it. Jess was the only one who was ever her equal. He had a really messed up life, but at least he felt conflict about how he treated Rory, though he always tried to make up for it too little too late. He was the only one who changed his actions for the better because of her and made it stick. Dean got into college because of her, but didn’t stick with it. Logan changed his actions because of his father.

    And the ultimate point is that when Rory was at her most uncharacteristic; when she dropped out of Yale and wasn’t speaking to her mom, the person that made her realize that she was completely lost, mostly due to her interaction with Logan and his family, was Jess. She totally snapped out of it, and went back to Yale and Lorelai ONLY after he called her out about quitting Yale, and dating Logan, and being lost. “I know you better than anyone, this isn’t you. What are you doing?”

  4. I was on and off with all of the guys, I liked Jess the best though in a way, just something about him. I do agree I wish that Tristan and her had been more explored. I would hope she would find someone closer to Logan but not like him either.

  5. I still want Rory to be with Logan. I think in the end, he was the best one for her, and definitely the guy I <3ed the most out of the guys she was around. Yeah yeah, Dean was sweet and he made her steal cornstarch after he kissed her the first time, but . . . LOGAN. Always Logan!

  6. Personally I like to think Rory went on her adventure and met up with an older and less douchetastic Tristan, the ever adorable Chad Michael Murray. I always felt they had chemistry that was never really explored.

  7. I liked Logan, but he wasn’t right for Rory for the long run. I was very glad when she turned down his proposal, and I think in the end he was rushing to get married and wanted someone to follow him on his grand adventures (instead of doing her own, like Rory). I think if she ended up with Jess again after some years alone to become an awesome journalist and find herself, I would be a happy camper. :)

    I just finished watching the entire series for only the second time, but in quick succession. I watched some of it when it was on originally, but for some reason I never saw the last season. It has quickly become a favorite!!

  8. Jess Jess Jess Jess Jess Jess Jess Jess Jess

  9. I think I am Team Logan as well because Gilmore Girls is like in real life, we saw Rory grow up and her first relationships were sweet but like ours, a little immature, learning from our mistakes blahblah. In real life either we don’t find the right person on the first seasons; it takes time. And I think that she found the right guy in Logan, so I was a little disappointed at the end but it leaves a lot of opportunities to Rory and I’m sure she’ll find an even better guy ! (yeah I know it’s a show !)

  10. WOW, I love this, this is probably the only thing my best friend and I “fight” over, must say I was a Jess fan while she loves Logan but nice to know we are not the only ones :)

  11. I barely started reading thais and already had to comment – I was drawn to read this because it was about Gilmore Girls but then you go and tie in Doctor Who – my mind is just blown! BigWhovian here, so I was totally caught off guard. Since this must obviously be the best blog post ever written, I will now continue reading :)

  12. Am I the only one who would be weirded out if Jess and Rory and Luke and Lorelai ended up together? Since Luke is Jess’s Uncle? I mean I guess sisters marry brothers… so it’s cool but it just seems kind of strange. I totally agree about Jess getting his shit together and calling Rory out for being irresponsible. I have said it before and I will say it again… Gilmore Girls The Movie Lorelai and Luke get married and Rory ends up with… Jess I guess or Logan… but not Dean. Nothing against Dean but he just doesn’t make the cut

  13. Somehow I feel like Rory and Logan never really broke up. The fact that he proposed (asking Lorelai’s permission and all that – argh! faux pas!) and wanted her to be *his*, well, I might have deleted all that from my mind. GG ended for me with Rory and Logan still together and god knows what happened after she returned from the campaign.
    I absolutely loved Rory and Jesse, and never before today, after reading these comments, I had pictured them having breakfast together and reading the newspapers, being all grown up and all. Sigh,
    That was a great show!

    • They broke up, he said something like ‘if you say no (to the engagement) we will be done, it will be it, I’ll be gone for good, there is no way we can ever be together again if you don’t take this ring’ And she said ‘no’, so. And btw he didn’t look really upset, I mean he was proposing to her a minute and the next they were done and he didn’t even looked sad, what’s up with that?

  14. Well, the creator/writer Amy Sherman-Palladino said that Rory and Jess were always going to end up together. But she left before the 7th season. We never actually get to see where they could have ended up. I like to think that they got their shit together and found each other again. I’m a hardcore Rory/Jess fan. Loved them in the beginning, love them until the very end.

    • Yep. I mean, there had to be a reason she kept dragging Milo back season after season… ;) and a reason she tried to get a 6-year contract with him…honestly I don’t think any of the cast or crew ever envisioned Dean as her soulmate; he was her first love and safety net. Logan was the way Rory was going to figure out that she really didn’t want to be a full time member of that world. Jess was always the one who understood her, who complimented her, who pushed her, who comforted her. But the drama was coming from the fact that neither of them seemed to be ready for the other at the same time. Other things kept seeming to get in the way. But I have no doubt it would’ve/should’ve ended with these two finally finding that perfect balance.

      Actually even Milo (before it was announced that Amy and Dan were leaving, but after he had filmed 6.18) said he thought Rory would have to end up with Jess and that he would be happy to keep coming in for appearances on the show if Amy/Dan asked him. Before everything went downhill :/

    • Especially as she was the one who inspired him to be a writer and he was the one who made her return to Yale again after her dropout and her time with the grandparents. I think they would bring out the best in each other.

  15. I like to think she met up with Marty ( aka Naked Guy) and they had the romance that was always meant to be. That or she ran away with her friends to follow a pair of magical pants….

    • Yeeees! Marty! Yeeeeesss! Don’t get me wrong, I liked all of her boyfriends in their own ways, but I like to think she ended up with someone totally other. Plus I just dug Marty.

    • Marty? God no! He always liked her but she never liked him THAT way!

  16. I’ll keep this short, Jesse!! Maybe it was their book connection. Maybe it was the bad boy he represented. I always loved their banter and chemistry the best!

  17. Jess was my favorite boyfriend of her’s but I don’t see them making it in the long run, but I wish they could have been together longer. I always really liked Dean and thought he was so sweet but, again, not for the long haul. And then Logan. He had his pros and cons but his pros always won me over, however, AGAIN, I don’t see them in the long haul. If one of those relationships had to last, however, it would have been Logan. But I think the way the writers set the show up is perfect – the order the boyfriends went in, and the fact that none of them lasted. She learned different lessons from each of them at the perfect time in her life FOR those lessons, and then the writers left her open to pursue her career, which has always been the most important thing to her besides her relationship with Lorelai. She’s not tied down and is able to take that job following the President around without worrying about a boyfriend/fiance she is leaving behind. She’s free to get herself established and somewhere along the way come into an adult relationship, which I don’t really think she had with Logan.

    Also, I just wanted to say, I’m a huge freaking Gilmore Girls fan. My best friend/roommate and I each own our own set of all seven seasons and have seen every episodes many, many times, and can quote entire episodes (and we do). We are constantly quoting all the different characters and whenever our friends hear us say something they don’t understand, they just assume it’s a line from GG. I don’t think there will ever be a show I like more, although Veronica Mars is definitely up there :)

  18. I hated Dean since the beginning!! Logan and Rory were a great couple because they made each other better. Logan was the spoiled brat who I grew to love(even after the whole boat situation). But yet, it worked….. But, deep down inside (and in arguments with my friends) Jess was the one. The episode when Jess invites Rory to his book party still makes the teenage girl inside me absolutely happy. In a parallel universe (and in any romcom), Jess and Rory would have a serendipitous meeting and fall back in love.

    • I totally agree with the romcom-meeting-falling-in-love thing – Jess was always my favorite and when he told her to get her act together and then she came to his book signing I literally squealed. I was so happy that he was getting it together and being the great guy you would get glimpses of when he was dating Rory!

  19. I loved Dean. I loved Jess. I mostly hated Logan.
    But… I think there is still someone out there better for her.
    Or she will end up back with:
    the one that loved her most – Dean.
    Or the one that understood her the most – Jess.
    Whenever one of them is truely adult enough for her <3

  20. both*

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