Dean Forester is the new guy in town and falls had for Rory Gilmore quickly after she shows him around Stars Hollow. Despite being from different social classes and going to different high schools, Dean and Rory date for much of the beginning of Gilmore Girls. Dean even tries to date Rory during her Yale career but it doesn't work out due to their different places in life.
Dean: (Pauses, confused) Corn's two for a dollar?
Rory: Jess has a black eye. Any idea where he got it?
Dean: That would be an extremely long list.