(Source: Pinterest/Fanpop)
1. Jess presents Rory with a challenge.
From "the Early Years" on, Jess kept Rory on her toes. He was never intimidated to push her to be a better person and offer constructive criticism.

And you know what? Rory needs that.

Plus, his expertise at witty banter was always on par with that of the Gilmores. Always.
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