Karen

RORY: But how are you gonna make Young Chui dump you? Just be a really bad date?
LANE: Oh, no, we’ve already talked to him. He’s totally on board … See, he’s in love with this Japanese girl named Karen who his parents don’t approve of, so he and Karen see each other secretly while his parents keep setting him up with nice Korean girls. He’s the male me.

Conveniently, the Korean boy Lane has been set up with already has a Japanese girlfriend named Karen, kept secret from his parents because they don’t approve of him dating non-Korean girls. Karen is a Japanese girl’s name meaning “lotus flower”.

Hypoglycemic

ZACH: Dude, can you chill out about your freaking elevenses ’til we get this song straightened out?
BRIAN: I’m hypoglycemic. If I don’t get something in my system, I’m gonna crash.

Hypoglycemia, the medical term for low blood sugar. Hypoglycemia may result in headaches, tiredness, clumsiness, trouble talking, confusion, fast heart rate, sweating, shakiness, nervousness, hunger, loss of consciousness, seizures, or death. It is usually caused by taking medications used to treat diabetes, such as insulin.

People sometimes use the word in a non-medical sense, to mean that they feel a bit faint or dizzy because their blood sugar has dropped due to not eating for a while. This is called “postprandial syndrome”.

Elevenses

BRIAN: I thought there was gonna be coffee, too.
ZACH: Dude, can you chill out about your freaking elevenses ’til we get this song straightened out?

Informal British for a short break for light refreshments, served in the late morning, around 11 am. Known in other parts of the world as morning tea, coffee break, or morning snack. Popular British children’s books such as Winnie-the-Pooh and Paddington Bear have made the word reasonably well known.

Bulwark

ZACH: [sings] “A mighty fortress is our God, a bulwark never failing.” Dude, what’s a bulwark? … It says, a bulwark never failing.
BRIAN: I think it’s a wall.

A bulwark is a defensive wall built as a fortification to protect a castle, town or city, so Brian is basically correct.

Michael Moore

LORELAI: And you couldn’t have taken two seconds at work to call and tell her that?
JESS: No.
LORELAI: Really? You don’t get breaks? Do you get food, water? Should I get Michael Moore on the phone?

Michael Moore (born 1954), filmmaker, author and left-wing activist. His documentaries frequently address the topics of globalisation and capitalism.

Dimebag at the Sadie Hawkins Day Dance

LORELAI: Most of us had first boyfriends like Brian Hutchins … Seventh grade, I’m sitting in the library, walks up, asks me to go steady. I say yes. He walks away and I don’t see him again until the tenth grade when he tries to sell me a dimebag at the Sadie Hawkins Day dance. And he was way overcharging for it, too.

In North America, a Sadie Hawkins Day Dance is one held, usually by schools and colleges, where girls invite boys, rather than the usual convention of boys inviting girls to a dance.

It comes from Sadie Hawkins Day in the Li’l Abner comic strip by Al Capp, an unspecified day in November when unmarried women could chase bachelors, and marry the one they caught. First introduced in a strip in 1937, by 1939 there had been Sadie Hawkins events held at over 200 colleges.

A dimebag is a small bag containing $10 worth (usually 1 gram) of marijuana. Lorelai’s forgetful admirer seems to have either charged more than $10 for it, or put very little product in the bag. Although Lorelai didn’t buy the marijuana from Brian, she knew enough about buying drugs to know he was trying to rip her off, suggesting some level of familiarity with the subject.

Comparing Dean and Jess

RORY: Sure, when Dean said he’d call, he always called, but where’s the fun in that?
LORELAI: Oh, honey, don’t do that.
RORY: Do what?
LORELAI: Compare Dean and Jess, that’s not fair. They’re different people.
RORY: Clearly. One calls when he says he will and one doesn’t.

Dean phoned Rory obsessively – five times a night was considered normal in the early days of their relationship, when Dean presumably felt secure and happy. As he became less secure, he phoned Rory to the point that she began getting impatient, and at the height of his paranoia, rang 14 times while Rory was working on a school project, which alarmed her a little bit.

However, Rory is now seeing Dean with rose-tinted glasses, and now all she can remember is that Dean was reliable at phoning when he said he would. Lorelai tells her it isn’t fair to judge Jess against Dean – but then says that’s because Dean is so obviously superior! It would have been more helpful if she reminded Rory of all the times Rory got fed up with Dean’s obsessive phone calls.