Dean vs. Jess

Here is my pro-con list of Rory’s loves. The winner will go on to challenge her next boyfriend in a pro-con list. Think of it as death match with pro-con lists. This is a list for the still bitter discussion which should Rory have chosen, Dean or Jess? I have always liked Jess more than Dean.  For all of Jess’ faults, after Rory broke up with Dean he said he had to go take care of something (break up with Shane), before he kissed her.  Which is more than I can say for Dean. However, the list has spoken. Did I leave something out? Disagree with anything? Leave a comment & let me know.

Dean Pro Jess Pro
Changes the water bottle
Lorelai likes him
Doesn’t get in trouble
Hangs out with Lane
Planning on college
Remembers birthday
Built Rory a car
Comfortable with the phrase “I love you”
Will watch movies with Lorelai & Rory
Reads a lot
Does things his own way


Dean Con Jess Con
Not a lot of common interests
Really likes sports
Doesn’t read
Doesn’t feel a need to travel
Breaks up with Rory quickly
Lorelei doesn’t like him
Stood Rory up
Used Shane because he couldn’t have Rory
Wrecked her car
Town doesn’t like him
Didn’t take her to the Prom
Not tall
Cuts school a lot
Gets in fights



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About Sarakastic

I've watched every episode of Gilmore Girls several times. I moved to a small town that reminded me of Stars Hollow. I've subconsciously had my haircut to look like Lorelai. Gilmore Girls is my life, I just have to find Luke. (Well, I didn't have a kid when I was 16, but other than that...)

9 thoughts on “Dean vs. Jess

  1. Trish Ryan

    I’ve never understood the anti-Dean sentiment. Tall, handsome, sweet. What’s not to love? Sure, he might not be a rocket scientist, but it made sense for Rory – having seen her mother’s lifetime of romantic angst – to go for someone straightforward and solid, someone she could count on. Unfortunately, straightforward and solid doesn’t make for great television. I didn’t thing ANYTHING could make me root for Jess, but a couple episodes of Logan was all it took…

  2. Girl Friday

    I can’t say that I loved either of her boys. I guess the lists tell me that it really just depends on what Rory is looking for…if she wants a tall puppy dog, then she should pick Dean…if she wants a smarty pants rebel, then she should pick Jess. Personally, I’d like her to explore other options!

  3. Kaitlin

    I always liked Jess the best out of all of Rory’s boyfriends. I liked Dean second best but I cant stand Logan.

  4. Anne

    I don’t know, they all suck.
    Alright, I like Jess sometimes. But I know that for me, for the 3 incredible first seasons, there is a before/after Jess. He screws everything up when he arrives. The quiet and nice to live town becomes victim of stealing, of bad pranks… His rebellion just pisses me off. & he was a jerk 90% of the time he was with Rory. But when he talks to Luke (“the girls I like don’t give a damn about me!”) makes us really understand him, and what he does has almost always a sense and a noble cause. Plus, in season 6, he proves that he really knows Rory. I liked how he talked to her honestly and how he stayed nice doing it.

  5. Anne

    Logan, I like him. I don’t like him for being rich and being exactly like all the rich people, I don’t like him for being narrow-minded and i hate the fact that he always seems to… control himself. This is weird.
    BUT I loved he tried to make Rory discover new things: she was waiting to do this kind of crazy things, she just didn’t dare to do them, and I am so glad she really had fun with him even if all of this didn’t have sense. He loves her very much, but he’s not fascinating by her like Jess & Dean were, and it is not bad for Rory’s ego to be treated this way.

  6. Caro

    I have to agree with Trish to some extent- I’ve never gotten all the Dean hate out there. Sure, he screwed up sometimes, but who doesn’t? He was sweet, really loved Rory and respected her and those important to her.
    I don’t get the Logan hate either. He did some pretty ridiculous stuff, I know, but he was basically a good guy. I don’t remember him intentionally hurting anyone and he grew up a lot by the end.
    As for Jess… I can’t stand the guy, at least his teenage version. Rude, intentionally cruel and a know-it-all. His adult self grew on me a lot, but there was still something about the character that annoyed me to no end. Definitely my least favorite of Rory’s boyfriends.

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