So I’m on my second rewatch of Gilmore Girls and as far as Rory’s boyfriends go, this is what I have to say about them:
Warning: SPOILERS AHEAD FOR THOSE WHO HAVENT WATCHED IT!!
- Dean: I love him but he can be whiny sometimes. His reason for breaking up with Rory at the Stars Hallow dance competition was reasonable in a way, but honestly I feel like he shouldn’t have broken up with her in a public place where everyone could see. He should’ve taken her somewhere private where it’s just the two of them to discuss the issue. Also, don’t get me started about the whole Dean cheating on Lindsey with Rory fiasco because that was crazy.
- Jess: Confession: I’m team Jess. Yes I know a lot of people won’t agree with me because they’re either team Dean or team Logan, but think about it. Jess was Rory’s best boyfriend. Bam! There, I said it. Think about it. Not only did they have so much in common, but Jess always appeared in her life when she needed him the most, and they believed in each other. He was the one that convinced her to go back to Yale when she was taking that break. Rory believed that Jess would be a better student if he actually attended class and did his work because she knew that he was smart, and later on in A Year In The Life, Jess believed that Rory could write a book about her life with Lorelai because he knew that she was a good writer.
- Logan: I hate him, like really hate him. He got her into a ton of trouble (cough cough STEALING THE YACHT cough cough) and is the reason why her downfall started. He literally cheated on her, was ashamed to tell her about his business deal that went terribly wrong, and yada yada yada. Also don’t get me started on their affair in A Year In The Life. He was cheating on his fiancèe and she was cheating on her boyfriend Paul. In conclusion, Logan is Rory’s worst boyfriend. Yup, I said that too.
- Paul: Including Paul on this list because I feel bad for him. Rory always forgets about him and she was cheating on him with Logan. He deserves better.
- Marty: Including Marty too because I feel like Rory should’ve given him a chance. They were besties and would’ve made a cute couple too.
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