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Gilmore Girls fans have spent the years since the series ended rewatching each episode and debating each character’s decisions. Rory Gilmore’s love interests are a topic of debate often. Each love interest has fans, and each man has positive and negative attributes. Still, we don’t think any of them were “the one” for Rory Gilmore.  

Dean Forrester was too traditional for Rory Gilmore

Dean was Rory’s first boyfriend, and even Lorelai Gilmore admitted he was the perfect first love interest for her naive and innocent daughter. He was protective and caring. He ensured Rory was safe and seemed to care deeply for the girl he noticed on his first day at Stars Hollow High. 

Dean Forrester and Rory Gilmore remeet in Stars Hollow as adults.
Jared Padalecki and Alexis Bledel in ‘Gilmore Girls: A Year in the Life’ | Neil Jacobs/Netflix

Dean, however, wanted something that Rory was never going to be able to give him. Dean Forrester was after a traditional marriage, with a wife who cooked dinner and a husband who worked and paid the bills. He didn’t envision a life outside of Stars Hollow, which would be problematic for Rory. The natural progression of their ill-fated union proves they were never right for each other. By the time they had entered college, Rory’s Ivy League world and Dean’s working-class roots clashed. 

Jess Mariano is a favorite of fans, but he was too unpredictable for Rory 

Jess Mariano wanted to date Rory Gilmore from the second he saw her in Stars Hollow. He didn’t care that she was dating Dean at the time, and he didn’t care that Rory sent him mixed signals. He was infatuated. Eventually, Rory and Jess got together, but their relationship was pretty awful. 

'Gilmore Girls' actor Alexis Bledel as Rory Gilmore sitting at a desk in a scene from 'Gilmore Girls: A Year in the Life'
Alexis Bledel as Rory Gilmore in a scene from ‘Gilmore Girls: A Year in the Life’ | Neil Jacobs/Netflix

Jess was standoffish, pushy, and frankly a bit difficult. He also abandoned Rory without initiating a breakup because he was being left back. Still, Jess has plenty of fans who see the angsty teen as someone who, as Rory’s intellectual equal, had potential. Sure, Jess and Rory liked the same books and music, but their relationship didn’t really grow and develop. As adults, they probably wouldn’t mesh either. Jess’ aggressive wild streak wouldn’t have worked with Rory’s need for structure. There is always a chance that could change, though. 

Logan Huntzberger was too spontaneous to be Rory Gilmore’s forever love interest

Logan and Rory met at Yale and carried on an intense relationship. Jess’ fans argue that Logan was too pompous and stuck up to hold a candle to Rory Gilmore’s other bad-boy love interest. There is another reason Logan wasn’t right for Rory. 

Alexis Bledel as Rory Gilmore and Matt Czuchry as Logan Huntzberger in Gilmore Girls
Alexis Bledel as Rory Gilmore and Matt Czuchry as Logan Huntzberger in ‘Gilmore Girls’ | Saeed Adyani/Netflix

Logan was kind and fun and really loved Rory, despite having limited experience in a serious relationship. Things between Rory and Logan wouldn’t have worked out in the long run because he was too spontaneous for the ever-cautious Rory. While he did pull Rory out of her shell and happily called her on her more self-involved moments, a marriage between them would have been too stressful for Rory and too boring for Logan. 

We don’t know enough about Paul to judge how he stacked up against Rory Gilmore’s other love interests 

Dean, Jess, and Logan are Rory Gilmore’s most discussed love interests, but there is one more. During Gilmore Girls: A Year in the Life, Rory dated a man named Paul, who she kept forgetting to break up with. We didn’t get to see a ton of Paul, but from what we learned, he seemed like a responsible, respectful, and perfectly nice guy. 

Jack Carpenter wearing a black suit and tie poses for a photo at the screening of 'I Love YOU Beth Cooper' Carpenter played Rory Gilmore's love interest in 'Gilmore Girls: A Year in the Life'
Jack Carpenter | Dimitrios Kambouris/WireImage

1 Way Logan Huntzberger Was Different From Rory Gilmore’s Other Beaus (Aside From His Money)

Was he the one for Rory? Obviously, not. Paul was far too boring and dependable to be the type of man Rory would be attracted to. We do hope that he found an equally non-descript woman to settle down with, though.