Kiss dating goodbye
When Rory comes out to him late and tipsy, Dean breaks up with her because he realizes their lives are going in completely different directions. As Rory softly cries, Logan Huntzberger (Rory's future boyfriend) steps in to comfort her.
In his final appearance, Dean does not see Rory, but rather Luke.
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.
Dean quickly leaves, and Rory and Lorelai get into a heated argument over Rory sleeping with a married man.
The situation causes tension between Rory and her mother.
Rory returns to Stars Hollow, and Lorelai tells her about the incident.
Dean and Lindsay attend a party together where Dean attacks Jess when he sees that Jess made Rory cry.At Dean's bachelor party, Dean drunkenly admits to Luke that he still cares deeply for Rory, and he would rather be marrying her.