Directing and writing credits:
"Twenty-One is the Loneliest Number" is directed by Robert Berlinger, written by Amy Sherman-Palladino. Berlinger previously directed these episodes:

It's no shock that the episodes penned by ASP are usually the strongest of each season. This one has it all: sad moments between Rory and Lorelai, heaps of passive aggression from Emily, a glimpse at Halloween in Stars Hollow, and Madeleine fucking Albright. "Friday Night's Alright for Fighting," "I Get a Sidekick Out of You," and "Driving Miss Gilmore" are three other favorites from S6.

Most batshit crazy outfit:
If I had Birkin bag money, you bet your ass I would have a tailor on hand to save me from ill-fitting blazers like this one:

Logan looks especially sloppy next to Emily Gilmore in her chic high-waisted trousers.

I know Paris is skint right now, but what the fuck is this apple dress? Did she sell all her good clothes to Beacon's Closet and only keep the Forever 21 rejects? I can't get a good photo of it, but there is a pink ribbon running the width of the dress at mid-thigh, along with a layer of ruffles. At least her hair looks good!

"We had to stop and eat first in case the food here sucked."

On a positive note, I love Rory and Lorelai's birthday party looks. Both women are wearing mid-length black dresses with sheer accents. Rory is better accessorized than Lorelai, with a simple necklace and heels that tie at the ankle (c/o Emily Gilmore). I could do without Lorelai's metallic glitter shrug and kitten heels, but these are minor complaints compared to past infractions.

Most irritating Rory or Lorelai moment:
Rory is most insufferable in moments like this:

Lorelai: So, what's new with you?
Rory: Oh, well, not much. I got my community service hours down from 300 to 104, so ...
Lorelai: God, the community should be well-served by now. They should build a statue of you when you're done.
Rory: Well, it's not just one community.

Does anyone watch Seth Meyer's Corrections? Rory would be a proud member of the jackals, writing in to let Seth know that the bus from "Speed" would explode if it went over 50 miles per hour, not 55. A light face slap would probably do her some good.

I'm splitting hairs here, but I guess Lorelai is mildly inconsiderate to Luke when she initially neglects to tell him that the top comes off her doll house. She also continues planning an elaborate Halloween skit that he has explicitly rejected.

Moments before this, Luke awkwardly plays with Lorelai's hair.

Number of times Rory or Lorelai treat their BFF like shit:
Rory is visibly upset when Paris announces that she's the new editor of the Yale Daily News; however, I can't really fault her for this. Paris breaks the news in a clueless way that suggests she hasn't even considered her friend's feelings. Even more than the separation from Lorelai, this news might be the biggest wake up call for Rory. The more time she spends away from school, the more out of reach her old goals become. She had probably been compartmentalizing so much and trying to trick herself into believing that she no longer cared, but her reaction to this news proves otherwise.

Sookie's only purpose in this episode is to provide sausage options for Lorelai's Halloween plans that forcibly involve Luke. Lorelai doesn't exactly treat her poorly, but she does seem unappreciative of Sookie's effort, per usual.

Did Sookie have this sausage assortment on hand or ...?

Best literary or pop culture references:
Sookie tells Lorelai, "I can't believe Rory's turning 21. It seems like just yesterday she was crying because you told her Charlotte Brontë couldn't come to her sleepover ... because she's dead." This is the Rory I miss! The one who cares about books and has zero interest in trust fund douches.

Stars Hollow weirdness:
Babette and Morey don't fuck around when it comes to Halloween. They set up elaborate gallows in their front yard and put on a performance that involves legitimate method acting from Morey. With a noose around his neck, he flops around like he's dying a slow and painful death, which isn't hard to portray since he's losing so much oxygen IRL that he will eventually pass out. While Lorelai watches a sneak peek of this performance, she and Babette have the following exchange as Morey visibly struggles:

Lorelai: Do you need help, Babette?
Babette: Oh, no. As soon as he passes out, his muscles relax and I can slide him right out. We'll be good.
Lorelai: Okay. See you guys later.

I hope Morey is chill with an accidental death, because it's bound to happen one year if they keep up this charade.

David Carradine is rolling in his grave.

Sharpest insult or one-liner:
When Shelby and Martin arrive at Rory's birthday party early, Emily gives them a polite "nbd" response to their faces but as soon as they're out of earshot, she mutters, "Tacky, horrid people. Why not just show up the night before with a sleeping bag?" This faux pas probably got them removed from the Christmas card list and all future event guest lists. Failing to heed the rules of Emily Post is WASP social suicide.

Books mentioned/books Rory is reading:
Richard is reading "Matisse the Master: The Conquest of Colour, 1909-1954" by Hilary Spurling when he and Emily awkwardly speculate about Rory's virginity (a disgusting concept).

Emily: Logan is certainly a very experienced young man.
Richard: Man of the world, Emily, man of the world.
Emily: You know, Richard, it might be that time.
Richard: What time?
Emily: She might be getting ready to have relations with that boy.

Emily and Richard's ignorance totally explains why Lorelai got pregnant at 16. In the same breath, they attempt to police Rory's sexuality while describing former playboy Logan as a bon vivant sophisticate. It makes me want to puke.

Stick to business and leave the sex education to someone who isn't stuck in 1950.

Best song of the episode:
In true Emily fashion, the soundtrack to Rory's birthday party is full of Blossom Dearie. "Always True to You in My Fashion" and "Everything I've Got" both play at different points during the night. However, my favorite song is Peggy Lee's cover of Willie Dixon's "Seventh Son," which can be heard in the background during Emily and Lorelai's outdoor conversation.

Thoughts:
This is one of those episodes where I feel bad for Rory, Lorelai, and Emily. Richard Gilmore, on the other hand, can go to straight hell. The first scene begins where "Welcome to the Dollhouse" left off: with Richard standing on Lorelai's porch, eager to talk about Rory. In a masterful bit of gaslighting, he attempts to convince Lorelai to work with him to concoct a plan that will land Rory back at Yale ... as if this isn't exactly what Lorelai tried to do immediately after Rory announced her drop out intentions. When it comes to her parents, Lorelai always seems to have more patience for Richard than for Emily. Although this conversation annoys her, Lorelai always responds with civility. She seems more resigned than angry. Had Emily shown up instead of Richard, a screaming match would have quickly ensued.

As Lorelai rants to Luke after her dad's departure, her sadness over Rory's impending 21st birthday surfaces. They had big plans to celebrate the milestone by drinking martinis and playing blackjack in Atlantic Titty (as Samantha Jones calls it). Now that they aren't talking, the plan will never come to fruition. This upcoming milestone is also on Rory's mind. In a dream sequence callback to "Rory's Birthday Parties," mother and daughter lay in bed together as the fuzzy alarm clock reads 4:03, the time of Rory's birth. Only now, Lorelai is played by former US Secretary of State, Madeleine Albright.

Rory previous wore these pajamas in S2 after she broke her arm.

In "The Gilmore Girls Companion," casting director Jami Rudofsky recalls that Amy would "ring up the casting office and rattle off a few names of high-profile politicos she'd like to see on the show." Albright, a big "GG" fan, was more than happy to make a guest appearance. USA Today (which I won't link because it's too riddled with ads) quotes her as saying, "I had watched "Gilmore Girls" because it was a good mother-daughter story and then when I left office, I got a phone call from the producers and they said would I mind if somebody played me and I said, 'Yes, I would mind. I want to play myself.'" No matter how you feel about her politics, I hope we can all agree that this is all very cute.

Later, after Emily interrupts Rory and Logan's awkward foreplay, the topic of her birthday is broached. Rory agrees to let Emily throw her a party as Logan stands by, mildly disconcerted that he had no idea her 21st was upcoming. When he asks her why she didn't mention it, Rory goes into the same Atlantic City spiel as Lorelai. She tells him, "My mom and I have been planning for my 21st birthday since, well, my first memory is kindergarten, but I have a feeling she was talking about it before then." Planning an alcohol-fueled extravaganza with a 5-year-old aside, it bums me out to see this estrangement drag on for more episodes.

Logan is lucky that Emily didn't see his shoes on the sofa.

As Emily throws herself into party planning mode, Richard dedicates more time to creeping on Rory and Logan. After he catches them "engaged in a round of serious necking" in Logan's car, he tells Emily that they need to "do something" before kissing turns into fucking. If they were really concerned with keeping Rory safe, they would have a conversation with her where they ask about contraceptive methods and consent. Because they're spineless control freaks, they outsource the sex talk entirely to Reverend Boatwright (Michael C. McCarthy), who is clearly a fan of abstinence-only education. I would be fucking pissed if I showed up for pot roast and instead got a lecture from an old white man about the "precious gift" of virginity 🤮 To her credit, Rory is polite but firm and somehow manages to stop herself from throwing a Parker House roll at the reverend's head.

As if being patronized by a minister isn't bad enough, Rory returns home from community service the next day to find the pool house stuffed with furniture. Emily claims that she had nowhere else to put the rental furniture for the party, but Rory understands that this is nothing but an elaborate cock block. (Or vagina block. Why is the cock always given priority?) It feels like no coincidence that as her situation with the elder Gilmores nosedives, Rory becomes more interested in testing the waters with Lorelai. When she learns that her mom hasn't RSVP'd to the party, Rory calls the diner and demands a response from Lorelai (by proxy of Luke). As soon as Lorelai knows that Rory cares, she doesn't think twice about accepting the invitation.

Lorelai's face after Rory calls and curses Luke out (jk, she just says "hell").

The party is relatively eventful, especially for this show. Emily, who looks gorgeous in a sparkly zip-up jacket, lets Logan know that her feelings for him have changed after the sex revelations. For once, Zack's presence is welcome. When he and Lane meet Logan, Guitar bluntly asks, "So, you're, like, rich, huh?" and renders him speechless. Paris and Doyle have a practiced schtick (that they use at least three times) to announce her editorship:

Paris: I mean, it's so incredible. Last year, I was sleeping with the editor.
Doyle: And this year, I am.

At one point, Paris instructs Doyle to "Come in a little quicker next time." When the news is broke in front of Rory, Lorelai, and Luke (who Paris doesn't remember meeting on multiple occasions), the sadness is palpable. Lorelai sympathetically looks at Rory because she understands that this must be crushing her. Rory glances at the floor in shame. It's a well-orchestrated scene that reminds me of this moment from "Frances Ha" but under sadder circumstances.

Here's one of Luke's funnier lines to momentarily detract from the melancholy.

Rory and Luke have a nice moment together where he gives her a pearl necklace that he inherited from his mother. I've always appreciated that Rory and Luke's relationship is not dependent on Lorelai. Luke refuses to pick a side in their stupid fight and treats Rory with the same care that he always did.

When Lorelai finally interacts with her parents, it doesn't go well. She and Emily have a conversation that involves heaps of passive aggression, not-so-subtle digs at Luke, and an indirect engagement announcement. Richard is too depressed about Rory to join the party and has spent the entire night holed up in his office, drinking alone. When Lorelai and Emily try to talk to him, all their most toxic family dynamics are present. Emily kicks off the drama by slut-shaming Lorelai:

Richard: We've failed.
Emily: No! We have not failed. We have not failed until that girl comes home pregnant. Then we've failed!

After Lorelai leaves, Richard's hits Emily with a healthy dose of misogyny, likely reminding her of the very valid reasons for their S5 separation:

Emily: What's wrong with joining the DAR? We both agreed she needed a job.
Richard: Fund-raisers and tea parties? It's frivolous and meaningless. She has more to do, more to be. I don't want that life for her.
Emily: You mean my life. You don't want her to be me.

I hate Richard Gilmore more with each rewatch.

When Lorelai and Rory finally get to talk, it's a nice moment that is rudely interrupted when the cake comes out and everyone starts singing "Happy Birthday." Once again, Rory is unceremoniously separated from Lorelai and thrust back into her grandparents' world. As the camera tracks in on Lorelai, her face falls. The final scene shows her and Luke driving back home in silence. In one of Luke's final good moments, he tells her, "You can pull link sausages out of me if you want." The mother-daughter reunion is imminent, but we'll have to wait a few more episodes before it happens.

Random observations:

  • The scene of Logan responding "hmm" to Rory's Madeleine Albright recollection is proof that even interesting dreams are boring for other people.
  • I want to live in a neighborhood where people take Halloween so seriously that I am shamed for a haunted house CD and caramel apples.
  • The cake tasting scene reminds me of the time when Rory and Lorelai conned Fran into giving up a bunch of wedding cake samples even though they knew that they weren't going to hire her.
  • Luke's casual Pia Zadora name drop is proof that his relationship with Lorelai is serious. I wonder if they watched "The Lonely Lady" (1983) together.
This movie is frequently referred to as the "Showgirls" of the '80s.
  • Rory's signature drink is champagne, vodka, pineapple juice, grenadine, and maraschino cherries. As Luke says, "Ohh, it tasted pink. I mean, like, really tasted really pink, like pink pink."
  • I can't picture Emily and Richard ever attending church, even on the holidays. I imagine they're the type who just donate a shit ton of money to ensure the preservation of their conservative values.
  • How has Rory only completed 196 hours of community service? Let's say that she started chipping away at it in July. This means she's had 3 months by her birthday, which puts her at roughly 16 hours per week. Even if she's working part-time for the DAR, she's probably still not averaging a full work week. My sympathy for her plight is nonexistent.
  • I always wondered why former editor Doyle didn't find this Paris comment insulting: "The last person that ran the shop was too busy ironing his petticoat to put out a decent paper." It's basically like telling him to his face that he sucked at his job.