S2, E9: When Rory and her classmate Tristan (recurring guest star CHAD MICHAEL MURRAY) are cast as Romeo and Juliet in a school play, a jealous Dean insists on attending every rehearsal, forcing Rory to beg Tristan not to tell Dean about the time she and Tristan kissed. Meanwhile, Lorelai has to endure Luke's teasing after she dates a much younger guy.