Rory insists that Lorelai go in with her to meet the headmaster – our first clear sign of Rory’s deep dependence on her mother, especially in situations where she has to meet new people. Lorelai doesn’t encourage it, and tries to send her off on her own with a wave and a smile, but when Rory begs her mother for support, Lorelai can’t say no to her. This pattern is set to continue into Rory’s adult years.
(It also makes us wonder – did Lorelai deliberately sabotage her wardrobe choices, hoping that she would look so embarrassing that Rory would not want her mother to accompany her? If so, her plan fails, and she looks like an idiot for nothing).