July 22, 2024


For those not familiar with Gilmore Girls, here is a quick summary. The show is based in a fictional town called Stars Hollow. It focuses on the lives of a mother and a daughter and those around them. Lorelai Gilmore, the mother gave birth to her daughter Lorelai Gilmore also known as Rory when she was 16. The series portraits both Lorelais’ growth as a mom, daughter, their love lives and their careers. This article’s focus is going to be Rory’s: the daughter.  As the show goes on, Rory has few boyfriends. Who do you think is the best boyfriend for Rory?

1. Dean Forester

First of all, Rory’s first boyfriend is Dean Forester. He and Rory met in Episode 1 and according to Lorelai later, he was the first guy that Rory set eyes on. Some could say that he was a great first boyfriend but I strongly disagree. He had his great moments in season 1 and few in later seasons but whenever he sees Rory talking to any guys, he becomes highly possessive of her. In the beginning, it seems like simple jealousy but it gets progressively more toxic than just healthy jealousy. After 3 months of dating Dean tells Rory “I love you” when Rory doesn’t say it back, he just walks away and decides to break up with her. Which makes Rory doubt herself a lot in the relationship more and I would say that is the definition of toxic boyfriend. Dean and Rory start seeing each other again after Dean’s married. Rory continues to believe that he’s gonna divorce his wife for her but never did. It’s not just one person’s fault. Rory was a bit foolish when she thought that he would leave her after getting married and having a life together. Dean continues to lie to his wife and Rory without stopping. I would say that he liked the stability of his wife and the thrill of dating Rory at the same time. Even though Rory and Dean start seeing each other after the divorce, it doesn’t work out due to Rory’s busy schedule at Yale and Dean’s three jobs.

2. Jess Mariano

After breaking up with Dean, Rory finds herself immediately in a new relationship with Jess Mariano. He can be best described as the new kid in the town, the bad boy. From Rory’s perspective it was like love at first sight. Even though she was in a relationship with Dean at the time. Rory continues to talk to Jess as “friends”. When Dean sees how she looks at Jess, he becomes more and more doubtful that she still loves him. After Dean breaks up with Rory. Jess and Rory start dating 2 days after. Even though he’s the bad boy, he talks to Rory consistently and tries his best to take care of Rory at times. Lorelai doesn’t approve of Jess initially since she never got to see the side of Rory fell in love with. Around Rory, Jess becomes more talkative and he talks to Rory about books, music, and his opinion. However, he rarely opens up about what’s going on in his life or what he’s feeling. Rory was frustrated at Jess in the beginning of the relationship about how he’s closed off. After a while she gets used to it. However, he disappears after fighting with Rory. Right after Rory’s graduation, she calls him and tells him that she’s done with him and she’s done waiting for him. After a while, he comes back to town to get his car. After Jess and Rory bump into each other a lot, he finally stops Rory and tells her that he loves her and once again leaves. Overall, I would say Jess is the typical high school boyfriend that almost everyone has. 

3. Logan Huntzberger

In Rory’s second year in Yale, she bumps into a guy who’s writing his number on her door thinking it was someone else. Then, a friend of his, Logan Huntzberger sees Rory and tells his friend to write his number instead. After a while, they meet again in the school news room. Then she learns that he’s a part of a secret society that Rory was researching for the school paper. After spending time together closely, they become close friends. Soon after, she decides that she wants to try “casual dating” which results in her realizing that she prefers relationships rather than unserious dating. So, she tells Logan that she would like it better if they remained friends rather than casually dating. Logan decides that he can try to be a boyfriend for Rory because he doesn’t want to lose her. Which ends with Rory making bad decisions that alters her esteem. To summarize, Logan is the boyfriend that you would have that you would tell your children and grandchildren about. 

The Best Boyfriend: Jess Mariano

Despite his flaws, Jess really had a big impact on Rory’s life. His love for books and that rebellious streak of his pushed Rory to think more independently and go after what she really wanted. They had their moments, good and bad, but Jess definitely left his mark on Rory and all of us who were watching. He helped her grow into a stronger, more confident person, always encouraging her to step outside her comfort zone and chase her dreams. Their relationship showed us that sometimes the people who challenge us the most are the ones who leave the biggest impression.

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