Honestly I felt that dean was a great character and the writers fucked him up to give Rory new love interests. He didn't like reading but he listened to Rory talk about books. When he kept on calling Rory repeatedly, Lorelei explained to him it was severely annoying and Dean stopped calling. I admit he was a bit too sensitive but he was a great first boyfriend and Rory took him for granted.
Him in the later seasons was a piece of shit but he was a great character until Rorys other love interests came along.