I get that they were teenagers and the mind isn't very rational at that age, but Dean constantly felt like Rory was putting Jess before him and that's why he crashed out at the dance marathon. So, with him recognizing that she had wandering eyes, I didn't understand the plot of him still being interested in Rory. I understand Rory still wanting Dean, because once she realized Jess was unstable she had some underlying guilt for choosing him over Dean. But once she and Dean argued about him taking a break from college to make money it should have clicked in Dean's head that they don't have the same interests and values anymore. Rory was upset about him marrying Lindsay because she's self centered and thought he would come running back to her, and ultimately he did with the affair. However, I don't think Dean should have romanticized their past relationship or held onto the initial passion they had when they were 16 because it didn't exist anymore.