The Gilmore girls get themselves into a number of cringe-inducing situations over the years, but one of the most classic ones has to be when Lorelai wears booty shorts to Rory's first day at Chilton. Obviously it isn't entirely her fault, but it doesn't make her impression on the stuffy and judgy Headmaster Charleston any better. Their relationship doesn't exactly go up from there — remember when Lorelai is pressured into participating in a parent group at Chilton? Sigh. High school.
In the revival, Rory attends an alumni event at Chilton in the "Spring" episode, and mentions to Lorelai afterward that the headmaster told her to "say hi" to Lorelai. Lorelai isn't fooled for a second and immediately calls her out, knowing that the headmaster is likely no bigger fan of hers now than he was before. Whatever. She still rocked those shorts.
