It’s officially fall, meaning that many of us are starting our annual Gilmore Girls (GG) rewatch. Here’s my breakdown of each of Rory’s boyfriends, and which one is the best. This ranking takes in account events from both the original Gilmore Girls series, and the Gilmore Girls: A Year in the Life sequel. I’ve been watching GG for many years now, and have probably finished the show at least 10 times, making me overly qualified to pass judgment.
As a disclaimer – there will be spoilers for the show contained in this ranking. In addition, these judgements and explanations of why these relationships ended are not necessarily the fault of all of the boyfriends. Rory is not the best person and definitely did some terrible things to expedite the ending of these relationships, but that’s a different topic.
Team dean
Dean was Rory’s first boyfriend, and their relationship starts off very wholesome and sweet. He’s tall, cute, and kind. Dean was perfect for Rory in Season 1 because of what she needed in her life at the time. He gave her the perfect first kiss in the supermarket, built her a car, impressed her mom, read the books she loved, and supported all of her exhausting events such as Rory’s cotillion (a.k.a. coming out to society), formals, 24 hour dance marathons, etc. However, he also has a lot of red flags. We start to see this in S1 Ep14 ‘That Damn Donna Reed’. Donna Reed was an actress in the 50’s, often portrayed as a good housewife. Dean expressed how he loves the idea of the 50’s style housewife, while Rory wants to go to Harvard and become a journalist. He became very explosive and angry at Rory’s disagreement over the values of The Donna Reed Show’, and it became increasingly evident that their goals in life didn’t align. There are some good moments, but more red flags become more and more apparent. He said “I love you” to Rory before she was ready, and became angry when Rory wasn’t ready to say it back. He becomes annoyed when Rory focuses on school or spends extra time at a book sale, gets extremely clingy and codependent, and becomes very controlling and jealous when Rory meets Jess. Jess is the local diner owner’s nephew, and he quickly begins to have a crush on Rory. Dean doesn’t like this, rightfully so, but would constantly try to “size up” Jess, and didn’t trust his girlfriend around him. Dean even starts a fight with Jess over Rory, and becomes physically violent towards others. Rory and Dean broke up a total of three times throughout the show, but eventually Dean breaks up with Rory due to Jess becoming too much of a distraction. Later in the show, Rory is in college and Dean is married to his perfect 50’s housewife. Rory comes home from school and ends up losing her virginity to Dean while he is still married. Dean ended up cheating on his wife with Rory, and probably would’ve done the same to Rory if they stayed together.
Team jess
Jess is introduced in Season 2, and is portrayed as the classic bad boy with severe parental and authority issues. However, a sweet and funny side of him is shown very quickly as a guy who likes reading, music, and matches Rory’s sense of humor. Jess is definitely the most complex character on this show, and is very misunderstood. He fits the trope of “Grumpy x Sunshine” perfectly because he is pessimistic and only likes Rory. Initially, he tried to pursue Rory even while she was in a relationship with Dean, and he succeeded. Rory and Jess started dating soon after Rory and Dean finally broke up in Season 5. To start with his pros, Jess is charismatic, has great chemistry with Rory, is very supportive of her journalism dreams (which Dean was not), and challenged her to always improve. However, during his younger years, Jess had no sense of direction in his life, and was rude to others. Jess’s major red flags however are that when he was in a bad mood he ignored Rory, tried to pressure her into being more intimate than she wanted, and finally, moved to California (across the country) without telling her, causing their breakup. However, Jess undergoes the biggest character growth out of all the characters in the show. Once Rory was in college at Yale and drops out, he gives her the reality check she needed. He encouraged her to continue pursuing her dreams, and through this motivation during S6 Ep8 shows how much love he has for her. He then says the iconic quote: “What are you doing? Living at your grandparents’ place? Being in the D.A.R.? No Yale — why did you drop out of Yale?!” This is what inspired Rory to go back to Yale, and get her life back on track. In Jess’s later years, he becomes more goal oriented, is a published author, and becomes a very kind and sensitive person. In my opinion, later in life Rory doesn’t deserve Jess. Rory went through a character regression while Jess went through major development.
Team logan
Rory meets Logan during her college years at Yale. Logan is initially shown as a nonchalant rich kid who “doesn’t do the whole girlfriend thing.” He encouraged Rory to step out of her comfort zone by visiting the Life and Death Brigade, and decided to make things exclusive with Rory despite his history. Their relationship was fun, and Rory was happy, but also careless. While with Logan, Rory really lost herself. She stole a yacht, dropped out of Yale, and stopped talking to her mom (who was Rory’s best friend). Rory dropped out of Yale after an internship with Logan’s dad, a major leader in the newspaper industry, saying she wasn’t good enough to be the journalist she’s always dreamt of being. Logan treated Rory dropping out of Yale as a joke, didn’t support her, and was completely insensitive while brushing it under the rug. Logan was also very jealous of Jess when nothing between him and Rory was happening at the time, and refused to communicate. Logan thought money and gifts would solve all of his problems with his relationships, and this got worse as he got older. Logan ended up proposing to Rory when she graduated from Yale and gave her an all or nothing ultimatum. This causes Rory and Logan to break up since Rory wasn’t ready to settle down. Lastly, as an older adult and years after the breakup, Logan and Rory continuously see each other while Logan is engaged. Essentially, he cheats on his fiancee with Rory and is no better than Dean in the end.
my final ranking
- dean
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Jealous, anger issues, and cheated on his wife. However, he was a cute first boyfriend in the beginning.
- logan
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Insensitive, irresponsible, no communication, cheater. Although, it was a fun relationship, good chemistry, and he pushed Rory to be experimental.
- Title
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Grumpy jerk, didn’t communicate initially but improved. Best chemistry, character development, and he pushes Rory to be better!