Ranking the Worst to the Very Best :: Seasons of Gilmore Girls

In honor of Gilmore Girls returning, I thought this ranking would be very apt. Just so you know, I am extremely biased. I ship Rory and Jess. Always have. Always will. So the ranking will reflect my otp.

Note: there will be typos. My editing brain has shut down. Also, the gifs won't coordinate with the season because that's waaaay too much work. Becca is a queen. She coordinated them for The Vampire Diaries ranking. *bows down*

Ranking the Worst to the Very Best . . .

Seasons of Gilmore Girls

Gilmore Girls was a show that ran from 2000-2007 and it followed a mom, Lorelai Gimore, and her daughter, Rory Gilmore, in Stars Hollow. The small town setting, the rapid-fire dialogue, and the genuine love between the mother-daughter relationship all make this a stellar show. Add in broody Luke (who we all shipped with Lorelai) and Rory with her numerous romances, and it was a show that you had to watch. If you haven't yet: Binge it. It's worth it.

7. The Season that Amy Sherman-Palladino Did Not Write (SEASON SEVEN)The final season of Gilmore Girls is unarguably the worst. It's one that I had to force myself to watch (because, hey, it's the final season!). But admittedly, I did refuse to watch the season finale. In my eyes, the show ended at season 6.

Lorelai gets married to Christopher -- so weird. And Logan and Rory are in a relationship almost the entire season. These ships were edging towards endgame, and even if both never made it there, they were given far too much screen time in a final season. 

It was very clear that Amy Sherman-Palladino (the creator of GG) was not a part of this season. It lost its magic.

The only slim highlight was Lane and her pregnancy with twins. It's just nice to have Lane still in the show after all this time. She's a favorite for sure!

  • Biggest Relief: Rory ends up turning down Logan's proposal. It's a relief that she didn't end her entire series romance arc with Logan, but it also royally sucks that all of season 7's romance amounted to nothing.

6. The Season Where Logan Enters & Rory Gets Arrested (SEASON FIVE)The entrace of Logan should have sparked a fire in the show, but for me, I could not get on the Logan train. He was a rich playboy who I never felt cared or treated Rory well. Instead, he shows up, they date, and rebel Rory ignites. Together, they steal a freakin' yacht! He was like kryptonite for her, in my opinion.

Loreli's brief relationship with Luke was a highlight, but it wasn't enough to overcome the character change that Rory was going through.  

  • Biggest Annoyance: Emily trying to break Luke and Lorelai up by inserting Christopher into the mix. No, Emily. No.

5. The Season that Lorelai and Rory Don't Talk (SEASON SIX)I debated whether to put this season at 6 or 5, but this ultimately won out. Why? Because I'm insanely biased and Jess comes back for one episode in season 6. Holla!

In all seriousness, this season had it's major lows. The bond and the banter between Lorelai and Rory is the highlight of Gilmore Girls. You can take out the romances and the show would still survive with them. Take out their relationship and you get kind of a crappy season -- which happened here. Lorelai is angry that Rory dropped out of Yale, and they're in such a heated battle that Rory ends up living with Emily and Richard. It's not the best situation.

Rory ends up going back to Yale after a visit from Jess (who obviously pushes her to better herself and go after what she wants, unlike someone *cough* Logan *cough*). You also learn how much Jess has grown in this episode, and the scene where he confronts Rory makes you realize how good they are for each other.

In terms of love interests, Logan and Rory have a small break up (yay!) where Logan sleeps around (*glares*) and then at the end they get back together (ugh!). The Logan rollercoaster train was riding full force. 

Lorelai and Luke start off the season engaged and end it not-so engaged, which made me scream at my TV. Why can't we have nice things?

  • Biggest Side Character No One Wanted: Luke has a daughter! What? Yep, and not only is April an incredibly annoying 12 year-old, but you can argue that she's the cause Lorelai and Luke call off their engagement. 

4. The Season Where Rory Goes To College & Dean Cheats (SEASON FOUR): The upside of this season is Paris and Rory as college roommates. While Paris can be a little annoying at times, it was still nice to see their friendship in college.

Rory and Lorelai don't have much in store for the love interest department for most of the season. Except for that one episode where Rory hooks up with Dean. Who's married. It's a big shocker, and it seems totally out of character. But characters do make mistakes, and this was a big one for both Dean and Rory. Rory also has to grapple with the fact that she was the other woman in the scenario. 

Another upside: Lorelai and Luke have their first kiss! Hear that? It's the heaven's singing.

Overall, it was just an okay season, but memorable for it being Rory's first year in college.

  • Biggest OMG: Dean coming back (after all this time!) to cheat on his wife with Rory. (And I'm never going to get used to calling Jared Padelecki Dean. So strange, Sam Winchester. So strange.)

3. The Season Where Rory Goes to Chilton & Meets Tristan (SEASON ONE)it started it all! This is the season we meet Rory and Lorelai. And while most people rank first seasons as the best -- for nostalgic reasons -- it has a firm place at number 3 for me. 

The highlights are Rory and Dean's really cute relationship. Not many shows open up with a character already dating someone and then have them still be together by the end (though I think they might have briefly split somwhere in the first season.) While I think Dean is a bland potato, it was very much a first high school romance and it settled into that mold nicely.

The arrival of Tristan (hello, Chad Michael Murray!) breathed some life into the show. He was jerk, but an interesting jerk. And no one can forget the Romeo & Juliet play.

Not a fan of Max (Rory's teacher) who ends up dating Lorelai. From the minute we meet Luke and he verbally spars with Lorelai, you know it's fate.

  • Biggest Side Character We All Wanted: Paris. Oh Paris. You loved her. You hated her. But it wouldn't be Gilmore Girls without her.

2. The Season Jess and Rory Officially Date & Then He Ghosts Her (SEASON THREE): We own many shows on DVD. But there are only two seasons of Gilmore Girls that we own. That's right: Seasons 3 and 2. 

The dance marathon is the standout episode. How can you forget it? It's the most dramatic break up with Dean. And this is where Jess and Rory officially become a couple.

We all think it's made to last because Season 2 was the breakout moment for his character and their chemistry. Unfortunately, Jess' arc takes a turn for the worse. He stops going to school and at the end of the season ditches Stars Hollow for California. It's heartbreaking. And while the death of the Rory/Jess relationship was the low point in GG for me, it couldn't bring down a whole season where we got Milo Ventimiglia killing it as Jess. 

I understood why they had to break up, Jess had a lot of growth to do (his character had his own struggles), and most of it probably had to be done away from Rory. But when he comes back (season 6) it really does show that they're the couple meant to be together in the end.

Highlights: Rory trying to get into Harvard. Lorelai is single -- which means more time to flirt with Luke.

  • Biggest Upset: Jess leaves for California. He basically ghosts Rory, and while we should have all seen it coming (he's the bad boy after all), it hurt nonetheless.

The Season Where Jess Enters And Dean Gets Jealous (SEASON TWO): There is no other season that will beat season 2. The force that is Jess barrels into Gilmore Girls without stopping.

 He's the bad boy that had instant chemistry with Rory.

It also made Dean pretty jealous, which made for plenty of funny episodes with Dean and Jess. Like Jess noting how tall Dean was. It was a little sad that Dean started to suffocate Rory, but we all knew that relationship was never meant to last. 

Underneath Jess's badboy exterior, we saw glimpses of something more. Like the episode where he crashes Rory's car and this happens...

Other notables: Lorelai (thankfully) breaks up with Max, and she starts setting her sights on the Dragonfly Inn. The plot arc with the Dragonfly is one of my all-time favorites with Lorelai, so I loved the addition here. Plus, we see more Sookie and that is a huge win.

The highlight of the season is the love-hate back-and-forth with Jess and Rory. It's the start of many of my favorite kinds of romances and it was done to perfection on Gilmore Girls.

  • Biggest Shocker: Jess and Rory have their first kiss. She kisses him at the end of the season and it comes out of nowhere! Not nowhere (we knew she liked him) but we didn't think the writers would take it there.

Best Episode of All Time: 
"A-Tisket, A-Tasket" -- the annual charity basket auction. It's the moment where bad boy Jess outbids Dean for Rory's basket. She goes with tradition and spends an afternoon lunch with him. We see jealous Dean. We see Jess trying to flirt with Rory. Sometimes it's awkward (I love some good awkward moments!) but it's also filled with juicy drama. For a small town rich with it, this episode walks away the winner.

Do you agree? What are your fav seasons? Sound off below! 


  1. I disagree, I love Logan. Dean was always a bland potato - I'll give you that and I LOVE Jared but Jess was a jerk. Yeah he had his own problems but he was horrible to Rory throughout their whole relationship - we still never found out the truth about his bruise when he goes to dinner with Emily that first night.
    I never felt the connection between them, I got excited at first because it wasn't Dean but once they actually started dating, I didn't feel it. Even in season 6 when he returns briefly, I can't help but think - maybe he is better off without Rory in his life? She seems to just complicate him and as a character not there to just be Rory's boyfriend he is a decent character and although you can see the new maturity in his arc, I just don't see him with her.
    How can you say that Logan doesn't care for Rory? Yes, he isn't perfect - far from it, but he's lovely to her. When he comes back to give her a kiss before he leaves - that is just adorable - I feel like Logan is a combination of both Jess and Dean, he has danger, like the stealing of the boat, but he is also sweet and looks after Rory's needs whereas Jess never did. How can anyone say he was perfect for her based on two episodes in Season 6 because from what I saw in Season 2 and 3 I didn't see it.

    Stealing a boat is far more tame that getting her in a car accident!

    I don't want to rant and in regards to the actual list, it is something I will mainly agree on except I would switch Season 6 & 5 on the list because Season 6 was horrible for the first half with Rory and Lorelai not speaking together.
    I just felt compelled to write this, everyone has their opinions and I respect yours, just as I hope you respect mine.

    1. U feel me. Rory should consider herself lucky that Logan is a love sick pup. And every girl are lucky to have one like that . He always cared about her wish . Like how Lorelai cared for her.

  2. The truth about the bruise of Jess is revealed in that same episode or the next!! He got "in a fight" with a swan!! It was funny!:)

  3. You have started great episode its excellent.
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  5. Whoever wrote this is Anti-Logan. Nothing better to do . I find Rory - Logan love is matured . Kind of real. And you hate that bitch .

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