Dean, Jess and Logan walk into a bar.

So since season 3 episode 21, we have been on the Gilmore Girls train together. Currently we are set to continue with season 5 episode 10. With one and a half season watched together – and the introduction of the last of Rory’s major three – we feel it is time to have a chat about the love life of one of our favourite Gilmores.


We therefore bring to you – for the second time – Rikke and Diana: chat edition.

If you haven’t watched as much Gilmore Girls as we have you should read on with caution.


“I’m so happy I put my viewing on pause and waited for you to catch up because now I have someone to parttake in the madness with me. As everyone probably know, some of the reason for me taking a break was the fact that Jess left because whereas you are not exactly pro Jess I am very much so. I think the dynamic of the two of Jess and Rory together is brilliant. Jess pushes boundaries with Rory but she in turn rains him in a bit. He has later even admitted that he was/is/will always be in love with her. I can’t wait to see what they have in store for is in A Year in the Life of with those two.”

Rikke_round “It is always more fun to be mad together! Since you brought up Jess, then let’s talk about Jess. I agree with you on everything, but I never really bonded – for a lack of a better word – with the character. My major issue with him is that he was introduced as a foil for Dean so quickly that I never got Jess without the relationship drama of Dean and Rory. But I will say that I too am excited for what happens in A Year in the Life. Jess and Rory has major potential, but not as teenagers.”

Diana_round“Basically you think of Jess as the bad pancake. I get what you’re trying to say but where Dean was the perfect first boyfriend Jess is really the one who makes sense with Rory – and I will tell you why. They have a lot of the same interests without becoming a “we/us”. Jess understands Rory’s need to read and intellectually challenge herself, but he also understands that she needs to let loose and have fun to function. He is the perfect mix of understanding and bad boy. He has some rough edges yes, but he really is a misunderstood teenager, though for one I really feel like Rory actually understood him. He stayed until that one part of his life that made sense didn’t anymore. To prove my point I do believe that it is some of the above qualities that makes Rory work with Logan, so it is definitely her type. Jess will always be the first second.”

Rikke_round“You might be right about the bad pancake. And Jess is the definition of a misunderstood teenager. He was kind of what Rory needed at that point in her life. She was clearly annoyed with Dean leading up to their second break up and Jess was all the things she was missing from Dean. I like Dean – as her first boyfriend-I assume we’ll talk more about her second relationship with him later – but he is not the type for a grownup Rory. Jess fits her better, but he has too many issues for it to work. He clearly craves love, but he doesn’t know how to handle it. I’m not sure he was actually ready for a relationship when they started dating. He needed to figure himself out, which by the looks of the trailer for A Year in the Life looks like he did. I don’t think I have much more to add to the Jess talk. So if you don’t have more to say, why don’t you tell me why you think Rory and Logan work? You do have a bit more knowledge of their relationship than me”

Diana_round“A bit more but not that much to be honest. Logan is exactly what Emily and Richard will love (spoiler: they do), he is everything Lorelai doesn’t want for her daughter and in my head he is the rich version of Jess – and yes a bit less teenage angsty. Logan is definitely the one I know the least about, as I haven’t watched as many episodes of the latter seasons before we began the marathon. Logan is a big part (maybe tool?) in the half season where Rory and Lorelai don’t speak (let’s not talk too much about this because I can’t handle it). I think Rory needs it to see if the life she could/should have had was actually robbed from her or if she is actually happy to have grown up less ‘fortunate’. Still it is a phase she has to get through to realise it was always Jess.”

Rikke_round“Always Jess, huh? I guess you played your card in what is essentially a discussion of who we ship Rory with. I know about as much as you do about Logan – and an old Television Without Pity recap of Veronica Mars where I learned that rich douches named Logan dated protagonists on CW shows. As far as shipping goes I simply cannot be Team Dean and I don’t know enough about Logan to be on his team. I did like the scene in You Jump, I Jump, Jack where they jump. It was cute. And unlike you I am not Team Jess – at the moment, it might change come November 25. I am therefore declaring myself Team Rory  as of season 5 episode 9, but I am definitely intrigued by Logan”

Diana_round“That is the easiest team pick ever. We are ALL team Rory. Generally we are really team Gilmore. Logan has some nice qualities that fit well with the story and with Yale Rory. I would have loved to have read that recap – I love the idea of rich douches named Logan dating CW protagonists – technically WB right? We don’t know enough about Logan to talk more about him, but I am sure we will have thoughts later. So we turn to Dean, why do you think he is such a great first boyfriend?”
#TeamJess #Always

Rikke_round“Just nitpicking a little here: Veronica Mars was never a WB show, it was UPN, but that is not what we are talking about. Dean, Dean, Dean. He was a great first boyfriend for Rory, because our little Rory was very innocent and to an extend naive when she started dating Dean. First Boyfriend Dean was therefore perfect, as he was sweet and patient – if you ignore his dumb response to Rory’s lack of respons to his declaration of love, but I’ll forgive him, because he was an insecure teenager – and just perfectly non-threatening to Rory and Rory’s relationship with Lorelai. That he later turned out to make bad decisions is sad, but he really was a great first boyfriend. Maybe a tad boring – Dean on his own is actually super bland – but it worked for Rory at the time.”

Diana_round“I quite agree but mostly because I think he was a great lead in to Jess – you thought we had moved past him didn’t you, but no I can always drop some Jess into a conversation. I just feel like Dean is two different characters. The bland Dean she dates in the beginning and then the mess that is someone completely else, who marries a random girl and then decides to cheat. What character development led to that happening? Nothing I tell you. I would have liked him to have been written out somehow rather than having him such a recurrent role in Rory and Lorelai’s lives. I am totally with Luke in the episode We Got Us a Pippi Virgin, when he tries to scare Dean off. Go away Dean. No one wants you Dean. Not even Emily and Richard.”

Rikke_round“And you know you are in trouble when Emily and Richard are on the same page as Luke. I don’t quite agree with you on the out of the blue changes in Dean. I think he was always a little sensitive to being loved and the only reason Dean and Rory broke up over Jess, was because Dean couldn’t ignore it anymore. I think he would have happily dated Rory while she was in love with Jess, if she just didn’t bring it up. Dean lives in a very simple world where the fact that he loves Rory excuses his cheating on Lindsay. Dean got married to the bad pancake and didn’t have the balls to figure it out, because then there was Rory and he was still in love with her, so in his mind I doubt he felt he did anything wrong. I have a harder time with Rory sleeping with Dean just because she knew Lindsay and Dean’s marriage was rocky. It is not that Rory is morally superior to that – because she does some dubious things – but she really ought to know that getting between two people in a relationship is a bad idea. She has been there herself before with the Jess/Dean drama and again on the outside with anything Lorelai and Christopher related. Okay that turned out a little rant-y, but now I don’t have anything else to add except that I look forward to the next chapter in Rory’s love life.”



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