Chill Pill

RORY: Maybe I didn’t study hard enough. Maybe I got cocky.
LORELAI: Maybe you need a major mud bath/salt glow/chill pill combo.

Take a chill pill is American slang meaning that the person addressed needs to relax. To chill means to act cool, and the concept of chill pills probably comes from drugs like Xanax, Valium, or even Ritalin, as if the person needs to start acting as relaxed as someone under medication. It dates to the late 1980s, with use peaking in the 1990s.

Lorelai humorously suggests that Rory should combine her “chill pill” with relaxing spa treatments such as a mud bath or a salt glow because she’s acting so stressed that a simple pill won’t be enough.

Shindig

DEAN: Hey Lane. Are you going to this big shindig at the inn tonight?
LANE: Yeah, I’m just trying to trick my mom into not going with me.

A shindig is an informal word for a small party, especially one that is lively, noisy, or out of control. Originally it was entirely rural, and seems to come from the American South, with the suggestion that the dancing was going to get so vigorous in such a small space that you’d literally be kicking people’s shins. It is not impossible that there is a connection with the Scottish Gaelic word sinteag, meaning “jump, leap”.

Ringer

LORELAI: He’s a ringer.
RORY: How do you figure?
LORELAI: Someone recruited him, promised him a handsome sum, financed his theatrical snowman accoutrements, so he could snatch victory away from a deserving local in order to bag the contest prize for himself.

Ringer is slang for a contestant who enters a competition under false pretences, such as a professional entering an amateur contest. It comes from horse racing, where a fast horse was sometimes substituted for a slower one, known as a “ring-in”.

Although Lorelai is being deliberately preposterous, it does seem a little mean for such an experienced competitor to enter a local contest in a small town, especially when there isn’t even a large prize to act as an incentive. He isn’t actually building a snowman anyway – he’s creating an ice/snow sculpture, which is a different entity. I feel as if he should be disqualified.

The Money Pit

MICHEL: How about ‘The Money Pit’?

In American slang, a “money pit” is any property, possession or business which takes up an increasingly large amount of money to maintain it – usually more than was foreseen or budgeted for.

Michel is possibly referencing the 1986 comedy film The Money Pit, starring Tom Hanks and Shelley Long as a couple struggling to renovate their recently bought house. It closely parallels the 1948 Cary Grant comedy, Mr Blandings Builds His Dream House, and received lukewarm reviews. The movie does have a happy ending, a possible foreshadowing that Lorelai and Sookie will have one too.

“Little chippy stowed away in Mount Pilot”

LORELAI: Do you think [Luke’s] dated anyone since Rachel?
RORY: I don’t know. Where would he meet anyone? He’s either here or in his apartment.
LORELAI: Maybe he has a secret life. Maybe he’s got a little chippy stowed away in Mount Pilot.

Mount Pilot is a fictional town in the sitcom, The Andy Griffith Show (1960-68). The show is set in the fictional town of Mayberry, North Carolina, and Mount Pilot is a neighbouring larger town. Mayberry is apparently based on the real town of Pilot Mountain in North Carolina, with its name inspiring Mount Pilot. (There is a real Mayberry in Virginia, about 22 miles from Pilot Mountain).

The archetypal small town of Mayberry was almost named Taylortown and had a sheriff named Taylor [!!!!!], and like Stars Hollow, only had one traffic light and a cast of lovable eccentric characters. Like Stars Hollow, it was about thirty miles from the state capital, and had a population of ambiguous size.

The name Mayberry is used in popular culture as a term to refer to idyllic small town life and rural simplicity. Lorelai is humorously using the name “Mount Pilot” to mean any real life neighbouring town to the “Mayberry” of Stars Hollow.

“Chippy” is dated American slang for a prostitute or promiscuous woman; it goes back to the late 19th century and is of obscure origin.

Little Debbie

LORELAI: Hey Little Debbie, your dad is definitely gonna be there.

Debutantes are often called debs for short. Lorelai turns this into Debbie in reference to Little Debbie, a brand of cookie and cake snacks that has a little girl on the logo.

It’s a product line of McKee Foods, and the company founders, O.D. and Ruth McKee named it after their granddaughter, Debbie, in 1960, even using her image to promote the products. Debbie McKee-Fowler is now the Executive Vice-President of McKee Foods.

Giant Foam Fingers and Wazoo

RORY: You know what I love most about Harvard?
LORELAI: No, what?
RORY: They don’t sell giant foam fingers.
LORELAI: No, they’ve got class out the wazoo.

Outsized hands cut out of foam are sports paraphernalia worn on the hand to show support for a particular team. They have been in use since the late 1970s.

The wazoo is American slang for “the anus”. To have a particular attribute “out of the wazoo” means to have it in abundance or to excess.