‘Ship Wars: Gilmore Girls

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

  • http://www.facebook.com/profile.php?id=505821671 Candice MacNeale Lazecky

    My bestie and I are are Team Logan all the way! I loved Dean, but I hated what they did with his character. I also hated the ending. I realize that not everyone is ready to marry their college boyfriend, but the reasoning behind her decision was stupid. Logan was right, if she loved him that way, and wanted to spend the rest of their lives together, she could have said yes. Married doesn’t mean you give up your dreams, and give up your lives, it means you have a partner there to help you achieve them, to lean on and to love. And you get to be the same for them. She should have just been honest (and by she, I actually mean the writer’s!). Because those of us who stayed with and eventually married the boy we fell for at 17, and now have 2 beautiful children(and 1 on the way) and a million amazing adventures and memories together, were flat out insulted by the way things went down! Plus, who says no to Logan??? Really!

    • http://www.facebook.com/profile.php?id=1014511992 Hannah Queiroz

      It was always gonna be Logan.
      She became an adult with him and he was the only one out of the three who could truly treat her like one. Also, he was the perfect balance in relation to the other people in her life: her grandparents loved him and Lorelai grew to like him – which never happened to Jess or Dean.
      Besides, who doesn’t love Matt Czuchry??? <3

  • http://www.facebook.com/profile.php?id=1652421693 Amalia Pantazi

    Well. Dean is definately out of the equation for me. I liked Logan, he could be a real jerk, but I did liked him. And you make a good point about him and he really was the one who was objectively best suited for Rory, in all aspects. The thing is, that I didn’t like Rory when she was with Logan. I think she sort of changed, and I don’t think it’s Logan’s fault, but still, I personally didn’t like the Logan Rory.
    This is why I am Team Jess. I loved Jess from the first moment he came on the show and I never changed my opinion about him, even when he was an asshole to Rory. He was a troubled kid and he did mess things up. However, I believe that Jess was the one who made Rory be her best self. In any case, Philly Jess was perfect for her. Like he’d said to her once, “he wasn’t ready before, but he was then”. I think that a relationship with Jess would have given Rory a thrill of adventure and excitement, but also an intellectual challenge, too, because she admired how Jess had evolved. And she would still keep her feet on the ground, much unlike in the sparkly Richie Rich world of Logan. Next to Logan, I think Rory would eventually become an Emily, and I would hate to see that. Next to Jess, I think she would be more of a Lorelai.

    • http://www.facebook.com/profile.php?id=696619351 Katherine Presley

      I had never really pictured it that way, but I think you’re really right about her future – next to Logan she would be an Emily and next to Jess she would be a Lorelai. I feel like Logan would have more and more of his father in him as he got older, and they would have to be part of “that” society which isn’t necessarily a bad thing but Rory could do so much more and I would hate to think of her just being an Emily, and how proper their kids would have to be – not as stifled as Lorelai but not as free as Rory, and Rory had, like, the perfect childhood. But next to Jess, she WOULD be more like Lorelai and their life would be full of music and books and intellectual stimulation and they would both write and it would just be really awesome and allow them both to be who they are meant to be. Of course, it would be kind of weird because of Luke and Lorelai being together – weird almost related but not really situation lol but family gatherings would be fun!

  • http://www.facebook.com/profile.php?id=506585130 Colleen Sweeney

    I will always be Team Jess. They were the most compatible, and that’s there is to say. I hated Logan, literally from the get-go. He treated her contemptibly, and was shocked that she refused his proposal. I didn’t have issues with Dean per se, but when Jess came into the picture, he acted like a douche. And then he cheated on his wife with Rory, and it just was downhill from there.

  • http://www.facebook.com/profile.php?id=598772502 Janaki Nagarajan

    Nope. Jess. From the moment they appear on screen together until their last, inconclusive goodbye, there’s something magical there. They can see each other’s souls in a way no one else can. People were absolutely unfair to him in the beginning, basically with the exception of Luke and Rory. Cut him some slack…he was 18 with a LOT of really weird family issues he had to get through. Mom who didn’t want him and shipped him away, dad who didn’t want him and left when he was born but then randomly shows up and runs away. Can you really blame an 18-year-old boy with those parents to be awesome at communication? I mean even Luke, his most normal relative was not naturally good at communicating. But Jess DID grow up. And my favorite thing about him is that he didn’t do it FOR Rory (like Dean and Logan tried to do), but BECAUSE of her. She inspired him. He genuinely realized he wanted more for himself. He didn’t do things just to try and win her back. She told him HE could be better, do more. Luke supported him. He knew there was more to Jess than met the eye. He knew the townsfolk’s accusations were unfounded. He became the kind of person who was perfect for Rory. And through her trials and tribulations, she became truly ready to appreciate Jess.

    I think Dean is just a jerkface slimeball, almost from the beginning. He’s creepy, he’s mean, he’s manipulative. (HE’s the one who threatened and later punched Jess. HE’s the one who screams at Rory and doesn’t trust her.) Logan is charming and I think she had to date him to know that’s not what she wanted but honestly he’s just a rich douchebag. He whines about his life but does nothing to fight it. He’s lazy and bratty…he embodies the opposite of every value of Lorelai’s. He doesn’t really care about Rory or understand her at all. (You can’t care about someone and be okay with having sex with like 3 people when you think you broke up). To even date him, she has to change everything about herself. Now she does this willingly, but I don’t think she realized just how much she had given up and was missing until Jess came back and shook some sense into her.

    • http://www.facebook.com/profile.php?id=696619351 Katherine Presley

      I love what you said about Jess changing not FOR Rory but BECAUSE of her – that she inspired him to be more because she believed in him. I think that is so true!! Dean and Logan changed to be with her or win her back but Jess changed when he had no contact with Rory and he did it for himself, and the only reason he really even told her about it was to thank her for making him see he could do more. Love Jess!

  • http://www.facebook.com/profile.php?id=1045592886 Nicole Buergers

    screw them all. Team Marty.

    • http://www.facebook.com/profile.php?id=62003515 Sarah Hunt

      Yes, Marty! Love him.

  • http://www.facebook.com/profile.php?id=516705772 Janice Lynn Dixon

    I am definitely on Team She Just Graduated, Go Out and Be Single Already.

    • http://www.facebook.com/profile.php?id=633747455 Rachael Berkey


      • Karen Belz

        *group high five*

  • http://www.facebook.com/profile.php?id=100006145260423 Gretta Burnette

    As a woman who is very in love with “a reformed bad boy,” I am definitely in favor of her ending up with Jess. Reformed bad boys make the best lovers and boyfriends. In my imagination, Rory encounters Jess during her adventures and they reconnect now that she is unattached. They live happily together and continue their adventures together.

  • http://www.facebook.com/profile.php?id=1163970004 Lauren Michelle Sergesketter

    I have always chosen to believe that she went off on the presidential trail, bumped into Jess on one of her appearances, and they lived happily ever after writing, reading, and listening to the most awesome music. And of course, making the prettiest babies ever imagined.

  • http://www.facebook.com/profile.php?id=679619487 Chris Clinite

    I am a Rogan fan. I like to think that after some time on the road with the campaign that maybe she and Logan reconnect a little further down the road and reunite.

  • http://www.facebook.com/profile.php?id=553435055 Elizabeth Polit

    Total Team Rogan. They both helped each other grow and become better people. And, they have the best episode together, a.ka. “You Jump, I Jump, Jack.” PLUS, think how pretty their babies would be. Seriously people, those would be some insanely pretty babies.

  • http://www.facebook.com/profile.php?id=504878487 Sami-Jo Cairns

    Through to the end, I was always a Jess fan, gripping on the remote, waiting for she and Jess to get together when he suddenly made his reappearance. His bad-boy leather-jacket wearing insurgence in her life had my interest peaked, but in the end he got it together and completed something he could be proud of and got into publishing – no matter how small his presses were.
    His background (to me) only gifts Jess more dimensions and creates strong character where he could have drifted into a pathetic nobody and let his past best him.
    Team Jess all the way!!

  • http://www.facebook.com/profile.php?id=1673770832 Jessica Wylie

    I always thought she would meet back up with Jess,bot of them ready/grown up to delve into a passionate love that lasted forever. They challenge each other and that is always the person worth sticking with.

  • http://www.facebook.com/profile.php?id=1673770832 Jessica Wylie


  • http://www.facebook.com/profile.php?id=219705958 Leah Renee

    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

  • http://www.facebook.com/profile.php?id=1231971231 Becka Jaroszewicz

    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.

    • http://www.facebook.com/profile.php?id=696619351 Katherine Presley

      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!

  • http://www.facebook.com/profile.php?id=696619351 Katherine Presley

    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 :)

  • http://www.facebook.com/profile.php?id=16828097 Vanessa Jay

    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!

  • http://www.facebook.com/profile.php?id=1482963628 Rachel Frumkin

    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….

    • http://www.facebook.com/profile.php?id=540249092 Marcela Xavier

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

    • http://www.facebook.com/profile.php?id=118502191 Beth Howard

      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.

  • http://www.facebook.com/profile.php?id=100000742380707 Laurel Reid

    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.

    • http://www.facebook.com/profile.php?id=1730635548 Nikolina Serdar

      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.

    • http://www.facebook.com/profile.php?id=598772502 Janaki Nagarajan

      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 :/

  • http://www.facebook.com/profile.php?id=540249092 Marcela Xavier

    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!

    • http://www.facebook.com/profile.php?id=1049763424 Brisa Amador

      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?

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