“You’re a Gilmore. It’s in your blood. You can’t escape it, and I can’t protect you from it anymore.”
Lorelai is terrified that Rory is becoming too comfortable with the "high society" lifestyle she herself ran away from. Seeing Rory fit in seamlessly with Richard’s business associates triggers Lorelai’s deepest insecurities.
The guide to this episode is really a guide to She spent years building a "shield" of pop culture, junk food, and independence. When Rory "wears the hat," Lorelai feels that shield cracking. Essential Quote:
Dean faces the ultimate "boyfriend test" when he is invited to the Gilmore house for dinner. Christopher (Rory’s dad) also makes an appearance, adding another layer of complex history to the mix.