Rory Gilmore Has Never Had a Good Boyfriend

As temperatures drop and leaves turn, autumn is on the brink. If you’re a true fall fanatic, the beginning of the season means an annual “Gilmore Girls” rewatch. With any rewatch comes the age-old question — who is Rory’s best boyfriend?

Dean Forester is the typical first love. Jess Mariano is the apathetic rebel. Logan Huntzberger is the rich playboy. 

The correct answer? None of them.

Rory’s first love interest is introduced in the pilot episode, as Dean observes her from afar before their romance begins in episode five. On their three month anniversary, Dean tells Rory he’s in love with her. She can’t say it back. Dean breaks up with her, thinking she doesn’t love him.

Dean’s insecurities drive his relationship with Rory. During their on-again-off-again relationship in the early seasons, Dean is constantly clingy, getting upset any time Rory has to study or do anything remotely related to Chilton. 

He was never supportive, but still expected her full attention. Even in later seasons Dean proves to be self-serving, as he cheats on his wife with Rory when she returns home for a weekend from Yale. 

Despite this, they’re smooth-sailing until Jess shows up in the second season. He immediately started pursuing Rory after arriving in Stars Hollow, despite her being with Dean. Jess takes a bracelet Dean made for her and doesn’t return it for two weeks, and he comes over to her house unannounced several times, disrupting her daily life. 

When Dean and Rory break up in the third season, she begins dating Jess just three episodes later. Jess is emotionally unavailable and doesn’t seem to care for Rory’s emotions. When he meets Rory’s grandparents for the first time, he is irritating and ungrateful. 

Arguably, Rory brings out the best in Jess, but he’s still a miserable punk to everyone — including Rory. He understands Rory and her aspirations, but he isn’t a good boyfriend. Near the end of third season, instead of breaking up with Rory in person, he leaves town for New York. Jess’ lack of guilt highlights his apathetic view towards Rory

While Rory tries to rebuild her relationship with Dean during her time at Yale, she meets Logan who’s rich, overly self-assured and constantly flirting with her. 

By the end of season five, Rory breaks up with Dean — again — and starts casually seeing Logan. During this time, Logan dates other people while Rory, despite agreeing to the arrangement, fumes. Two episodes later, Rory and Logan officially get together. 

One night while trying to cheer her up, Logan takes Rory out and together they steal a yacht. This gets her arrested and as a result she has to complete over 300 hours of community service, leading her to drop out of Yale. 

Logan doesn’t care enough about Rory. He’s focused too much on partying and his wealth instead of his relationship, and it puts a strain on them. Because he lacks focus with Rory, he’s never truly a part of the relationship.

While Rory is out of school, she and Logan take a break. When Rory returns to Yale she reconciles with Logan, but while they were on a break Logan slept with several other people. Rory finds out about this and gets upset — only to forgive him one episode later. 

Logan has never had the stamina to be in a long-term relationship, especially one with someone as ambitious as Rory. No matter what relationship he’s in, it won’t be healthy. He’s too weak to break out of his rich lifestyle and attitude. 

Despite all the ups-and-downs of their relationship, Logan proposes to Rory after her graduation. Rory turns him down, but during the revival episodes, “A Year in the Life,” Logan and Rory meet again and she starts casually seeing him while he has a girlfriend.

All three of Rory’s main love-interests are self-serving manipulators who hold her back — so as the episodes start rolling, and the pumpkin candles are being lit, remember Rory Gilmore has never had a good boyfriend.