HEADMASTER: Like mother, like daughter. LORELAI: Okay, hold on. HEADMASTER: Ms. Gilmore, active participation in Chilton activities for a parent is vitally important.
The phrase “like mother like daughter” can be found in the Bible, in Ezekiel 16:44. There, it specifically refers to the city and people of Jerusalem, who are said to have the Hittites as their “mother”. It isn’t complimentary, meaning that Jerusalem has taken on the same disgusting practices as earlier cultures, despite the love and protection of God. The proverb seems to have been well-known even in Old Testament times.
You can see Headmaster Charleston in the role of disappointed God, having offered the love and protection of Chilton to Rory, only to find that she has inherited her mother’s appalling habits!
A phrase that seems to have arisen in 1950s hipster culture, to mean that someone has submerged themselves in the counterculture to the point that they no longer fit in with conformist society. Once used as praise, today it’s usually used sarcastically, as Rory does, to mean the person is too pretentious or above themselves to lower themselves to normal standards of behaviour.
LORELAI: Yes, I have. I’ve also done the ‘chip on my shoulder’ bit. Ooh, and the surly, sarcastic, ‘the world can bite my ass’ bit, and let me tell you, I mastered them all, in heels yet.
Lorelai is referencing a famous saying about Ginger Rogers, who was Fred Astaire’s dancing partner in many musical films: “Sure [Fred Astaire] was great, but dont forget that Ginger Rogers did everything he did … backwards and in high heels”. If it did not originate with him, it was at least popularised by Bob Thaves in a 1982 Frank & Ernest cartoon.
The quote is used to imply that women often have to work harder than men to gain a similar recognition, or have to do so while maintaining a “feminine” image which requires a lot of discipline and upkeep.
In this context, it doesn’t quite make sense, unless Lorelai thinks that being a snotty ungrateful teenager counts as some sort of “work” that gets you somewhere in life, and which is made harder for girls than boys.