SOOKIE: Oh I should make some kiwi ice cream. That would be good sometime.
Sookie means ice cream made from kiwifruit, not from the bird called the kiwi, or New Zealanders.
“A good walk spoiled”
RICHARD: Now, what do you know about golf?
RORY: That it’s a good walk spoiled?
“Golf is a good walk spoiled” is a humorous quote commonly attributed to Mark Twain, who almost certainly did not actually say that. The source of the quote cannot be identified.
Forscape and D.S.S.
RICHARD: Do you know the merger of Forscape and DSS happened right here on this lawn?
Two fictional finance companies.
FBI
RICHARD: Everyone [at the club] has to go through a thorough screening process.
RORY: Kind of like the FBI?
RICHARD: We’re much more thorough than that.
The FBI is the Federal Bureau of Investigations, the United States’ domestic intelligence service.
Country Club
In real life the main country club in Hartford is the Hartford Golf Club in West Hartford. It does look like the sort of place where Richard Gilmore would feel at home.
It doesn’t have a rose garden, which Emily told Richard to be sure to show Rory at the club. However, Elizabeth Park in West Hartford has a famous historic rose garden and is less than ten minutes drive from the golf club. While this probably wasn’t what the scriptwriter had in mind, in real life it would be possible to take Rory golfing and to see a rose garden in the same morning.
Exterior shots of the golf club were filmed at Brookfield Farms in Thousand Oaks, California – the same place exteriors of the Independence Inn were filmed.
Tiger Woods
EMILY: [gives Rory a hat] Here you go. Now you look just like Tiger Woods.
RORY: Wow, that’s some hat.
Eldrick “Tiger” Woods (born 1975) is a professional American golfer and among the most successful of all time. He became the World #1 in 1997, less than a year after turning professional.
I can find no instances of Tiger Woods ever wearing a woolly hat such as the one Emily gives Rory, and clearly it’s going to take much more than a hat to make Rory look anything like Woods.
“She’s a sixteen year old”
RICHARD: She’s a sixteen year old who would rather be at the mall.
Does nobody in Rory’s family know that she hasn’t turned sixteen yet?
Midgets and clowns
MICHEL: Just let me know when the midgets and clowns arrive.
Michel means as part of the circus freak sideshow that he considers the double twin wedding to be.
Doublemint
LORELAI (referring to the double twin wedding): It’s like a really snooty Doublemint commercial.
Doublemint is a peppermint-flavoured chewing gum made by Wrigley. For a long time, their advertising used identical twin sisters as models in their advertisements. The longest-running Doublemint Twins were Linda Ryan Puffer and Lisa Winters Cox, who appeared in six commercials together between 1985 and 1995.
Teacher in the Charlie Brown cartoon
LORELAI: You don’t care at all, do you?
MICHEL: To me you are the teacher in the Charlie Brown cartoon.
Michel is referring to the popular Peanuts cartoon strip by Charles Shultz, featuring Charlie Brown as the main character. In the original cartoons, adults were referred to but never drawn, and this continued with the first television special.
The 1967 Peanuts television special You’re in Love, Charlie Brown had a classroom scene which had interaction with a teacher named Miss Othmar. Her voice was represented with a wah-wah sound made by a trombone. Since then all adult voices have been represented by the trombone sound.
The reference is made by people to indicate that they’re not listening, or that what they’re hearing is going over their heads. It seems an odd thing for Michel to know about, but perhaps he watched a lot of cartoons when he moved to the US to improve his colloquial English.
The Annotated Gilmore Girls 