Gilmore Girls Love Triangle Synopsis

Kylee Johnston

Here are my thoughts on one of the Gilmore Girls love triangles!


Dean was Rory’s first boyfriend. They were both two young 10th graders and they thought they fell in love. Dean and Rory’s relationship is a little abstract. They dated for almost 2 years, and they were not compatible at all. They didn’t grow as people, when they were together. They didn’t challenge each other. They were immature and young so when they grew they thought they were meant to be because they grew to each other so young. He was her best friend. Her safe place. They were purely platonic, but that doesn’t mean they weren’t supposed to date. Their relationship taught Rory the difference between love and ‘in love’. They went through what they went through to show each other what dating shouldn’t be like. He was a great first boyfriend, she felt safe with him. They were best friends. She was spoiled. Rory lost her virginity to him because she felt like she was supposed to lose it to her first love. 


Jess was Rory’s first love. Her first heartbreak. Jess and Rory were perfect for each other, they were the definition of soulmates. Jess loved her from the moment he met her. She tried to deny her feelings for so long, but she couldn’t stay away forever. He doesn’t like most people but he liked her from the start. They are so compatible. Like Rory said, “you need to find someone compatible, but not so compatible that they’re boring.” Jess is that. Jess challenged her, and she challenged him. They grew with and off each other. The problem with Jess and Rory is that they met at the wrong time. They were too young and immature to understand and handle love. Jess never loved anything, or grew up with anyone loving him. Rory taught him what love is. Jess gave Rory a sense of reality. She was sheltered her whole life, and Jess had a lot of problems and went through a lot. Jess showed her that life kind of sucks, but it is how you make it. She was in a bubble and everyone acted as if she was fragile. She never had to handle hard problems. He kind of said, “wake up Rory”. He was scared, and stuck so he left. They never broke up, they just left each other. Jess wasn’t welcome in Stars Hollow, and he had to redo his senior year. He needed to leave, that was meant to happen. In order for Jess to really grow, was to move away. Jess offered Rory to go with him, which would have been so good for them. But not at that time. Rory was in college. She was studying at Yale. Her dreams were finally coming true, when Jess got his act together. The timing for them was a split second off. But, Jess will love her forever. He will never not love her. They were meant to be. 


Wow, what can I say about Logan and Rory. After Jess, Rory kind of lost herself. When she dropped out of Yale and started doubting herself he stood by her. Well, he was the perfect college boyfriend for her. She wasn’t looking for anyone when she met him. He snuck up on her. Rory was at the time thinking Dean and her went through everything they did because they were meant to be. Little did she know, she would think differently. Dean and Rory had another phase because they both thought all the complications were just delaying the inevitable. They knew they were going to get back together. They were basically children when they dated and Dean really loved Rory. Dean was different to Rory though. Rory knew it, but tried to ignore it. He knew it wasn’t working out, and that was the end of them. They were done forever, and they both knew it.  Logan comforted her and grew on her. They became friends, but Rory still held back a little, knowing about guys like Logan. Logan is a snobby, privileged boy who can get problems fixed with daddy’s check book. He never really had to work for anything. Especially girls; they would just come right to him. Rory was different of course. Logan was completely fascinated by her. Their families intertwined, and Rory’s grandparents were close friends of the Huntzberger’s. They were both very attracted to each other.  Friends with benefits wasn’t enough though. Rory and Logan got jealous. They decided to start dating, and yes they went through their complications but they lasted most of college. They became each other’s rocks. His family didn’t approve, but he didn’t care. They started to fall in love. Pure love. He showed her what she deserved. They had a powerful and all consuming love. They were never boring. He challenges her and respects her too. He’s always there for her, and is always supportive. Logan was starting his life, and Rory was just discovering and experimenting hers. That’s why she denied Logan’s proposal. They were meant to be. They were meant to last forever. Logan was ready and I see where Rory’s hesitation is coming from, she was so young. But, Logan excited her and had a positive outlook on life. She was always tense and scared, he helped her break out of her shell. She should’ve said yes to his proposal, because he always taught her to say yes to things and go for it.