Rory and Jess were perfect for one another.

In the beginning, they had many shared interests and great chemistry, but she was still so sheltered and need to focus on her career, and he was immature and erratic from issues that stemmed from the poor job his mom did raising him. So, it never worked out. They had a lot of growing up to do. 

And they did. They grew up and found their individual purposes/passions. 

They understood one another without ever trying to make the other person someone they weren’t. 

They challenged each other. They made each other better. 

She was the only one who could convince him that he was good enough and could make something of himself…And he ended up writing novels and running a small publishing company.

He was the only one who could convince her that she had gone off the rails and was wasting her life partying, working for the DAR, and dating Logan…And she ended up going back to Yale, finishing her degree, graduating, dumping Logan, and getting a great journalism job.

Jess was Rory’s soulmate and one true love…

And no one can convince me otherwise.