Gilmore Girls Fans have spent the years since the series ended rewatching each episode and discussing each character’s choices. Rory Gilmore’s love interests are often a topic of discussion. Every love relationship has fans, and every man has positive and negative qualities. Still, we don’t think any of them were “right” 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 made sure Rory was safe and seemed to care deeply about the girl he’d noticed on his first day at Stars Hollow High.
However, Dean wanted something Rory could never 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 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. When they entered college, Rory’s Ivy League world and Dean’s working-class roots clashed.
Jess Mariano wanted to date Rory Gilmore from the second he saw her on Stars Hollow. He didn’t care that she was dating Dean at the time, and he didn’t care that Rory was sending him mixed signals. He was infatuated. Eventually, Rory and Jess got together, but their relationship was pretty awful.
Jess was reserved, pushy and, to be honest, a bit difficult. He also left Rory without initiating a breakup because he was being left behind. Despite this, Jess has many fans who see the anxious teenager as someone who had potential as Rory’s intellectual equal. 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 would not have resonated with Rory’s need for structure. However, there is always a chance that something will change.
Logan and Rory met at Yale and had an intense relationship. Jess’ fans argue that Logan was too pompous and snooty to rival Rory Gilmore’s other evil love interest. There’s another reason why Logan wasn’t right for Rory.
Logan was kind and funny and genuinely loved Rory despite having limited experience in a serious relationship. Things wouldn’t have worked out between Rory and Logan in the long run because he was too spontaneous for the always cautious Rory. While he pulled Rory out of her shell and called her happy in her more self-centered moments, a marriage between them would have been too stressful for Rory and too boring for Logan.
Dean, Jess and Logan are Rory Gilmore’s most talked about love interests, but there’s one more. During Gilmore Girls: A Year in the Life Rory was dating a man named Paul whom she kept forgetting to break up with. We didn’t see much of Paul but from what we learned he seemed to be a responsible, respectful and downright nice guy.
Was he the one for Rory? Obviously not. Paul was far too boring and reliable to be the type of man Rory would be attracted to. However, we hope he has found an equally unassuming woman to settle down with.