MIA: I miss you. Hey, do you realize it was fifteen years ago almost to the day?
LORELAI: Yes it was.
RORY: What was?
MIA: To the day when this skinny little teenage girl showed up at the inn. She had this tiny little thing in her arms.
LORELAI: A little thing named Rory.
The date appears to be 31st October 2001, although there is no mention of it being Halloween. Presumably the parties and celebrations will be in the evening, offscreen. If it is fifteen years, almost to the day, since Lorelai and Rory arrived in Stars Hollow, then it would have been in late October or early November 1986, when Rory was two, and Lorelai eighteen and a half.
In 1986, Halloween was a Friday. If Lorelai arrived in Stars Hollow that weekend, then she could have arrived on Saturday the 1st of November. The connection with Halloween gives Lorelai’s entrance into Stars Hollow a magical feel, as if forces beyond our ken were at work to bring the Gilmore girls to this starlit little town. That weekend would have also been the Autumn Festival, which remains a touchstone for the Gilmore girls throughout the original series and into the revival.
Perhaps more interestingly, they came to Stars Hollow just days after Rory’s second birthday. It makes you wonder what occurred to drive Lorelai to flee her parents’ home, because she doesn’t seem to have made a planned, measured, or calculated approach to running away. The show makes it sound as if she grabbed Rory and a few essentials, jumped in the car and drove at random until she found somewhere that would take her in.
Although I think it is safe to assume that things had always been fraught with her parents, there must have been a final straw around the time of Rory’s birthday which triggered her sudden flight. Did Richard and Emily shower Rory with luxurious gifts, so that Lorelai began to fear they might buy Rory’s love or make her spoiled?
Was there an extravagant party (shades of Rory’s sweet sixteen), where even a baby Rory was being pressured to perform to exacting Gilmore standards, did Emily become so demanding that every detail of the party be perfect until Rory was stressed and crying?
All just speculation, but fascinating to imagine. The seeds of Lorelai’s mistrust of allowing her parents near Rory must have sprouted somewhere, and we know it began early.