2x09 - Run Away, Little Boy
When Rory (Alexis Bledel) and Tristan (Chad Michael Murray) are cast as Romeo and Juliet in a school play, a jealous Dean (Jared Padalecki) insists on attending every rehearsal, forcing Rory to beg Tristan not to tell Dean about the time they shared a kiss, while Lorelai (Lauren Graham) has to put up with Luke's (Scott Patterson) teasing after she dates a much younger guy.