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Rory and Dean dated for most of Season 1 until Dean revealed that he is building Rory a car for their anniversary, and he tells her that he loved her. As the dance wears on, he can no longer stand by and watch it so he publicly breaks up with Rory, pointing out to both Rory and Jess that their feelings for each other are "so damn obvious." She is a little confused as to how she feels about Dean moving on.
Rory reacts badly to this, stating that she needs time and this is a big step for her to take. Rory drops significant hints (like at the town meeting) that she misses Dean and really does love him, resulting in him turning up at Chilton where Rory tells him that she loves him ("Dean! As for Dean, it's clear that he still carries a torch for Rory.
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Luke later finds Rory and Lorelai who are about to attend Dean's wedding, and he tells them not to go.
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And now the actor who played Rory’s first love, Jared Padalecki, is dropping some tantalizing clues.
We already knew that Rory would probably not end up with Padalecki’s Dean.