Season 1

21 episodes · 2000

When Rory is accepted to attend a prestigious prep school, Lorelai must swallow her pride and ask her wealthy parents for help paying the tuition.

Rory's first day at Chilton doesn't go smoothly: First, Lorelai's attire offends Emily and the headmaster; then Rory meets some obnoxious classmates.

When Rory and Richard bond during a day of golf at the club, Lorelai feels jealous of Rory's deepening connection with her grandparents.

After Rory receives a bad grade on her English paper, Lorelai helps her cram for a big Shakespeare exam – but catastrophe strikes on test day.

Lorelai admits she has feelings for someone. Meanwhile, Rory has a budding relationship of her own that is moving forward.

Rory clashes with Emily when Emily plans a formal birthday party for her. Meanwhile, Lorelai organizes a casual get-together to celebrate.

Rory shares a romantic moment with Dean, but doesn't tell Lorelai. When Lorelai hears about it from Mrs. Kim, she invites Dean over for movie night.

Snow strands Rory at her grandparents' home, while Lorelai spends the day with her beau. Meanwhile, Lane misses Rory and comes to visit.

Rory attends her first dance with Dean but they get home late, causing Emily and Lorelai to fight over Lorelai's mothering skills.

Misfortune strikes at the Gilmores' Christmas party. Dean assures Lorelai that nothing improper happened the night he and Rory fell asleep together.

After Paris causes a scandal by exposing the relationship between a parent and a teacher, she is confronted.

Lorelai goes on a hellish double date with Sookie, Jackson and Jackson's odd cousin. Meanwhile, Rory double dates with Dean, Lane and Dean's friend.

Trouble ensues when Rory takes her friends to a Bangles concert in New York. Lorelai learns something about Luke's romantic past.

Rory and Dean argue about women's roles after watching "The Donna Reed Show." Emily makes Lorelai face her feelings.

Rory's father returns, causing tension in Emily and Richard's house – and forcing Lorelai to make a big decision about her family's future.

Rory and Dean celebrate their three-month anniversary, but things don't go as planned. Luke's ex-girlfriend Rachel arrives in town.

After recent events, Rory keeps busy, refusing to give in to self-pity. Meanwhile, Stars Hollow's residents rally around her, much to her dismay.

When Lorelai's grandmother offers a trust fund for Rory's education, Emily fears losing contact with a financially independent Lorelai and Rory.

Emily is horrified when she sees the place where Lorelai and Rory first lived, so she sets out to create a perfect bedroom for Rory in her house.

Still upset over recent events, Rory becomes angry with Lorelai, who didn't tell her that she is dating again.

Rory finally tells Dean the truth about how she feels about him. Sensing something between Lorelai and Luke, Rachel makes a decision.