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Dean gave Rory her first kiss in the episode in Doose's Market  , where Dean worked for most of the series. 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. Rory reacts badly to this, stating that she needs time and this is a big step for her to take. Dean breaks up with Rory, but she doesn't tell Lorelai why. 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! Once Lorelai tells him that he may need to give her space in order for her to want him, he backs off. However, he later simply states to Lorelai on her porch that he can tell Rory is into Jess.