Between the two of them Rory and Lorelai date a lot of different guys. Some are wacky, some are sweet, and others break the Gilmore Girls hearts. It’s even trickier for Lorelai because she has to think about who would be a good stepfather for Rory but at the same time make sure that Rory doesn’t get too attached to someone Lorelai isn’t sure about.
I think one of the best boyfriends on the entire show is Dean. He is Rory’s first boyfriend and I wish that he would’ve been the last. At first it looks like he’ll cause some trouble between Lorelai and Rory because Rory wants to stay at her public high schools to be with him. However, later on Dean enlists Lorelai’s help and is determined to get her approval so that there won’t be any conflict in Rory’s sight. In that way it’s pretty apparent that he is truly a prince, although not quite exciting enough for Rory unfortunately.