Rory had two boyfriends while she attends Chilton: Dean and Jess, but she is single when she graduates. Despite going through her whole life with Harvard as her dream school, Rory decides to attend Yale University where her grandfather was an alumnus.
Chilton Preparatory School Rory attends the prestigious Chilton Prep for the rest of her high school career.
To pay tuition, Lorelai asks her estranged parents for help and they agree to pay on one condition: Lorelai and Rory must attend a weekly "Friday Night Dinner" at pm.
It wasn't until she began school at Chilton that her grandparents became a regular presence in her life.
Her father was rarely around during her childhood years.
She finishes her first year in the top 3% of her class.
Notably, Rory's rocky beginning at Chilton is shadowed by a group of three girls, Paris Geller heading the trio.Max Medina eventually takes a special interest in Rory and after the incident, reaches out and tells her he has extra credit options that can help her make up for the missed test.Rory begins to blossom at Chilton, and shows her potential to be a great and gifted student.Though born in Hartford, Connecticut, Lorelai raised Rory in Stars Hollow where her mother originally worked as a maid at the Independence Inn.Rory had limited contact with her grandparents, Richard and Emily Gilmore, when she was growing up, usually only seeing them during the holidays.This is substantiated by Rory's unwillingness to alter her predestined future, admit when something goes wrong or even accept that mistakes are good for her, instead feeling any "failure to comply with the prerequisites for her Gilmorian future" equal her being a failure as a person.