LORELAI: You’re comparing me to my mother? … I’m Emily Gilmore? My, how the mighty have fallen.
A common expression meaning that those who were once powerful have now been reduced to a lowly status. The idiom comes from the King James version of the Bible, and is first found in Samuel 2 1:19, where it laments, The beauty of Israel is slain upon thy high places: how are the mighty fallen!
Lorelai always prided herself on being a “cool mom”, and now she discovers she’s actually a mother. A mother just like her own mother, Emily. Rory could hardly have said anything more hurtful to her. Bring on the tourniquet, her heart is bleeding.
RORY: OK, the whole concept a free soda is that it’s free, you don’t have to work for it.
DEAN: Sorry you gotta sing for your supper.
To sing for your supper means to provide a service for someone in order to earn a favour from them. The saying is well known from the 18th century English nursery rhyme Little Tommy Tucker, although it was in use before that.
The episode title is a common phrase referring to betraying secrets, especially sexual ones. The idiom comes from the 1695 play Love for Love by William Congreve, with the quote being: “And if he needs must kiss and tell, I’ll kick him headlong into Hell”.
Kiss and Tell is also the name of a 1945 comedy film directed by Richard Wallace and starring Shirley Temple in the lead role of Corliss Archer. It was based on a 1943 Broadway play by F. Hugh Herbert, in turn based on his Corliss Archer short stories; Herbert wrote the screenplay to the film. The movie is about two teenage girls, and the trouble that ensues in their families when they become interested in boys, just as there are ructions when Rory gets a boyfriend.
RORY: I do however reserve the right to change my mind.
LORELAI: That’s your prerogative as long as you remain a woman.
Lorelai is referring to the saying that “It is a woman’s prerogative to change her mind”. The proverb may come from law: from the Middle Ages onward, if a man broke off an engagement, he could be sued for breach of promise since he had broken a contract. But a woman was allowed to back out of an engagement with no legal repercussions, although there might be significant social ones.
Even though today both men and women are legally allowed to change their minds when it comes to marriage, the old saying remains.
LORELAI: Will you help me push other people out of the way if they’re going for my size [at the shoe sale]?
RORY: I’ll even run interference for you.
To run interference is a term from American football or gridiron, meaning to legally block opponents in order to create a clear path for the ball carrier. As as idiom, it means to help someone while they perform a task without directly intervening, such as deflecting attention away from them so they can work in peace. Rory may be literally planning to block people at the shoe sale though, giving Lorelai a clear path to the sales desk.
LORELAI: Oh no! Drella, to your corner now [Drella leaves]
Telling someone to go to their corner means that they should shut up or go away. The saying comes from boxing, when a fighter retires to their corner during rounds.
PARIS: Me too.
LOUISE: Oh small world.
Louise is referring to the common idiom, “It’s a small world”, used to express surprise that you have something in common in another person. The saying is centuries old with no known origin.
LORELAI (on learning that Rory overheard her secret): Well, the best laid plans.
A paraphrase from Robert Burns’ Scottish poem, To a Mouse, on Turning Her Up in Her Nest With the Plough, November, 1785. The original lines are The best-laid schemes o’ mice an’ men/Gang aft agley, commonly translated into English as The best laid plans of mice and men often go awry.
The idiom means that the most carefully detailed plan can go wrong when put into practice.