LORELAI: The money goes to charity. I look cute. Case closed. Oh finally, the coffee cavalry arrives.
Lorelai is referring to the classic trope in Western films where the US Cavalry charges over the hill just in time to save the battling settlers from Indians. It was a favourite in D.W. Griffith films from the early twentieth century.
Lorelai is saying the coffee is arriving just in time to rescue her from the conversation. Apparently when she is wearing a cowboy hat, she thinks in Western cliches.
LORELAI: Hey, four menus, a coffee and an anvil please.
LUKE: What’s the anvil for?
LORELAI: For Rune.
Lorelai is referring to a common trope in cartoons where an anvil is dropped on a character’s head with hilarious results. It seems to have first been used in Disney animated films, and was perfected by Warner Bros. in their Looney Toons cartoons. (Possibly not a coincidence that Lorelai sees Rune off with a “Bye, Loon”.
The comedy anvil drop may have its origins in real life. A traditional celebration on the Fourth of July in America was launching an anvil into the air with gunpowder from atop another anvil, then watching it fall onto the other anvil with a thud. Presumably everyone stood well back during this exciting spectacle and hopefully nobody got an anvil on the head.
Sookie and Jackson have been shown doing nothing but bicker over the quality of his produce since the start of the show. In the conventions of romantic comedy, when two people keep arguing “like an old married couple”, the audience knows they are destined to be together some day.
Sookie is genre-savvy enough to know that the person she has been bickering with must be her romantic destiny: Jackson even acted like a jealous lover when Sookie checked out somebody else’s fruit. She takes immediate action, showing that she really is quite the relationship expert.
Her choice of Jackson is a practical one for another reason: she said she didn’t have time to meet people as she was so busy at the inn, so it makes sense for her to ask out someone she knows through work.
It is notable that while Sookie is always interested in Lorelai’s potential relationships, and gently pushes her toward Luke (her obvious romantic destiny in the show), Lorelai doesn’t reciprocate. She’s never said anything to Sookie except to grumpily tell her that as a long-term single, her opinion on relationships is worthless, and has never given her the tiniest nudge towards Jackson, who they both see nearly every day.
LUKE: Twelve guys stood in a row all night waiting for an enemy that never showed. They got stood up. They should’ve been wearing prom dresses.
Referring to a common trope in film and TV where a girl is stood up by her date when attending prom (a formal school dance). Rory later suffered this fate in Gilmore Girls.
BABETTE: How is he in the sack? …
LORELAI: I’ll call you during the cigarette.
Lorelai is referring to a common trope in film and TV whereby a couple are shown in bed smoking to indicate that sex has occurred.