Directing and writing credits:
"Swan Song" is directed by Chris Long, written by Daniel Palladino. Long directed a few previous episodes:

"Presenting Lorelai Gilmore" - Sure, Rory comes out at a debutante ball, but the main thing to remember about this episode is that Emily Gilmore wears an impeccable gardening outfit.
"The Bracebridge Dinner" - Lorelai and Rory build a Björk snowwoman and Clara makes her first irritating appearance.
"Help Wanted" - Lorelai helps Richard buy a coffee maker while Rory deals with the aftermath of her car accident.
"Haunted Leg" - Rory is jealous of Shane and mad that Jess didn't pine for her all summer while she was away at student government.

Most batshit crazy outfit:
Without a doubt: When Alex drops off Lorelai after their weekend away, she is wearing a pair of sage-khaki pants, a deep turquoise turtleneck, and the jacket that can only be described as a cheap halloween costume version of the cowardly lion.

Lorelais-Cowardly-Lion-Jacket-Swan-Song-Gilmore-Girls
Billy Burke's haircut is almost as perlexing as Lorelai's jacket.

Also of note, Lorelai’s graphic tee tracker: In this episode we see yet another graphic tee with a potentially racist image of an Asian woman and Lorelai’s “raunch and comfort” Bunny Ranch tee-shirt.

Most irritating Rory or Lorelai moment:
I have so many thoughts on how poorly Rory handled the dinner at her grandmother’s and her relationship in general, but I will save those for later.

The most irritating Rory or Lorelai moment was at the very opening of the episode. Emily is ragging on Gran. Then Lorelai rags on Emily for ragging on Gran. Specifically, Lorelai complains that Emily has been talking about Gran for nearly 20 minutes. Lorelai, the woman who later spends an entire night shitting on a play, won’t give Emily 20 minutes to shit on a person who actually causes her stress.

Number of times Rory or Lorelai treat their bff like shit:
None! This must really happen more in the later seasons.

In this episode, Rory facilitates Lane’s band practicing at her mom’s house, and Lorelai takes Sookie and Jackson to New York with her boyfriend, boring Alex.

Best literary or pop culture references:
There were a lot this episode, but my favorite is definitely Rory and Jess’s discussion of "The Holy Barbarians" and the Lipton family. Jess says he can’t believe that a beat would have had a son who was so stuffy and conservative, and Rory jests that maybe James Lipton is not so conservative after all. This tickled me, since this episode was written years before we all found out that James Lipton is more like his dad than one may think.

James-Lipton
Q: Did you represent more than one girl? A: Yes, a whole bordello.

Stars Hollow weirdness:
Miss Patty commits kidnapping and unlawful restraint against almost a dozen citizens of Stars Hollow and holds them captive while testing out her new One Woman Show. Kirk is the director and tells her to alter her memories so that Bette Davis is a murderer. They put up flyers pointing to Rory and Dean -- Rory and Dean! Two of the most boring people in the world! -- as supporters.

Sharpest insult or one-liner:
It is a true tragedy that there weren’t more scenes written between Emily Gilmore and Jess.

Emily: So. Rory tells me you’re a member of the Walmart Corporation?
Jess: Only out of necessity.
Emily: They sound like wonderful stores.
Jess: Oh yeah. I want to be buried there.
Emily: We’ve never actually been inside one, but we own the stock.
Jess: Thanks for the paycheck.
Emily: Oh that’s very funny.

Jess should have given Luke some pointers. He handles Emily way better than Luke ever could.

Books mentioned/books Rory is reading:
I think "The Holy Barbarians" is the only one. Book tease.

Best song of the episode:
No music of note. Miss Patty sings “One for My Baby.” Christians can rock, but Zack is not playing Creed.

Thoughts:
I have so many opinions about this episode, and I fear that some of them will be unpopular. So be it. Let me just say this at the outset: I am firmly #TeamJess over #TeamRory in this episode. There are so many times she acts like an entitled priss! It drives me fucking crazy.

The episode starts with two annoying Lorelai and Rory moments: The Friday Night Dinner conversation that I found to be the most irritating moment of the episode, and the juxtaposition of Rory and Lorelai’s planner styles. Listen, I’m not one to talk here. I spend months leading up to the new year thinking about what brand/style of planner I am going to buy. But I also know a successful trial lawyer who doesn’t make any notes in her files, but never forgets a single detail of a case. I wouldn’t recommend it, but ... whatever works.

The next day, we see Rory and Jess talking on a park bench about Rory’s new book, The Holy Barbarians. This is a little thing, but I too would be annoyed af if someone showed me a cool book and then told me that I couldn’t read it for awhile. Jess calls Rory a “book tease” all full of vocal fry. He’s into it. Then Rory begins her very annoying mishandlings of her and Jess’s relationship.

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Here's a tip: when dressing in monotone, do not choose poop brown as your color.

Mistake #1: She committed Jess before even asking him. She should have told her grandmother that she would ask him if he could get Friday off instead of just insisting that he did.

She puts Jess in an uncomfortable position, but he ultimately decides to go.

After Rory gives up her copy of the book in exchange for Jess’s presence at FND, she gets wrapped up by Miss Patty and kidnapped into her studio. I tried counting. I think there are about a dozen other citizens who have been held captive. Rory immediately seeks out Dean (whose hair is… insane) and the two of them have lame banter about the show. Meanwhile, Kirk is telling Miss Patty to re-write her memories so that Bette Davis becomes a murderer. Miss Patty starts to sing “One for My Baby,” and Kirk turns on the strobe lights. Several hours later -- it’s dark by the time they leave! -- the strobe light is still going on. I hope there were no epileptics in the audience.

When Rory gets home, she is wearing this very sad early-aughts long sleeve thermal. She hears some thuds at the door and opens it, in her horror, to Lorelai and Alex making out (or, as Lorelai calls it, “necking”). This is the first of several times that Lorelai and Rory’s sex lives are juxtaposed together. Both are in new relationships, both are feeling randy. Here’s my question: Do Lorelai and Rory ever talk about Lorelai’s sex life? Has she told Rory that she and Alex are boning? How can she be surprised that Rory doesn’t have the best experience with sex and relationships? Lorelai doesn’t seem to be very transparent herself.

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The placement of the lacing does her tits zero favors.

Lorelai and Rory’s (first) awkward discussion of what type of signal they should set up so not to interrupt each other is ended by Jess calling. And that brings us to:

Mistake #2: Rory should just have been super chill and mentioned that she was with Dean up front. Then Jess would never have had reason to question what was happening.

Jess gets over it soon enough. All he wants is to not see it on a telephone pole. Fair enough. He even feigns interest in the town gossip.

(Can we take a moment here and appreciate the advertisement on the flyer: The town mailman said, “Even without proper postage, this show delivers.” Precious.)

I’m going to skip most of the stuff with Lane’s band. Lorelai buys them personalized snacks, including melba toast. We see how very stupid Zack is. And we see once again how knowledgeable Ms. Kim is about music: (“With just guitar, it’s a little flat.”)

I do love the way that Dave shows Lane his love for her. The way that he plans so thoroughly to hide their relationship and engage in these zany plans with her really touched me. It reminded me of when I was in college and I went to a party at my boyfriend’s friend’s house. It was a disgusting place. Truly vile. Shane went in the bathroom before I did and put toilet paper down on the toilet seat. 💖 I think little actions that show love are really lovely, and Dave clearly is willing to put in some work to make Lane’s life a little easier.

For the sake of time, I’m also going to gloss over the fact that Luke has memorized Lorelai’s wardrobe and become an expert on the theater scene. (He likes The Producers. Hairspray was just alright.)

When Luke tells Lorelai to go get a copy of a book of walking tours around Manhattan, Lorelai walks in on Rory “necking” with Jess. Horizontal on a couch. Do you think Rory ever kissed Dean like that? No way. I loved Luke’s plan to keep them safe. When he pulled out that box of junk, I melted a little.

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Ten minutes is enough time for a teen boy to cum twice. What is Luke thinking?

OK. Now to the good (bad) stuff.

Emily is the real hero of the episode. She is so kind and warm and generous to her granddaughter during Friday Night Dinner. Again: It’s the actions that show our love. She bends over backwards to make Rory feel comfortable. But Rory is freaking tf out before Jess even gets there. Emily simply points out that there was traffic on the 84 and tries to assuage Rory’s nerves. She wants so badly for this to be a nice bonding experience with her granddaughter.

Then Jess rings the bell, and Rory sees it. DUN DUN DUNNNNN: The black eye. Emily breezes right over it; she doesn’t even mention it until it’s brought up.

Mistake #3: Rory should not have begun her inquiry into Jess’s black eye with agitation and accusation.

This is something I learned from experience. I am a criminal defense lawyer, and I cross-examine for a living. You cannot have a calm, warm conversation in which you ask your partner to open up to you by starting from a place of accusation. Let the dude take off his jacket. Ask him if he’s ok. Don’t ask him if the black eye is why he’s late.

(Emily, the hero, notes that they already knew the 84 was backed up: “We knew that too. There was something with a big-rig, and apparently all the men who drive them are hopped up on bennies and goofballs.”)

I’m going to guess that Jess doesn’t drive in traffic all that much. He doesn’t go to fancy dinners. He is hungry. The Gilmore house is intimidating. Rich people probably make him feel uncomfortable.

FND-Swan-Song-Gilmore-Girls
Who wouldn't feel awkward eating dinner served by a uniformed maid?

Mistake #4: Instead of trying to make Jess feel comfortable -- easing the tension -- Rory repeatedly ignores Jess’s feelings and her responsibility to make him feel more comfortable around her family.

Mistake #5: Rory makes assumptions.
She goes out of her way to keep focus on Jess’s black eye and questions him over and over (and over and over) about what happens. I would leave too! I can relate to feeling uncomfortable around a boyfriend or girlfriend’s family. Mix that with the stress of wanting to make a good impression, terrible traffic, and having an embarrassing (and painful) black eye. And then to add insult to injury, Rory insists that she knows best and accuses Jess (repeatedly) of getting into a fight with Dean. Come on, Rory. Dean isn’t cool enough to punch Jess.

There were so many good lines during this scene. My favorite was probably the back-and-forth between Jess and Emily about Walmart. A close second was Emily’s graceful maneuver: “Oh my god! There’s no salt and pepper on the table. We’ll need it for the meat!”

The dinner gets worse and worse until Jess leaves, and, once again, Emily does everything she can to make Rory feel comfortable.

Meanwhile in New York, Lorelai spends the night going to a shitty, boring play with her nice but boring boyfriend and Sookie and Jackson. She wakes up in a bathrobe after spending the night with her boyfriend to call and check in on Rory. Rory tells Lorelai that she’s still at Emily’s, and Lorelai pretends to be outraged at Emily’s presumed bad behavior. Apparently making assumptions is a shared trait. I loved how quickly and ferociously Emily turned from sweet to sour when Rory hands the phone to Lorelai and leaves the room.

Emily: How can you let your daughter be with that abominable thug? First he’s late. How disrespectful! Then he’s rude to Rory. Rude to me. Oh and that attitude! I wanted to slap that monosyllabic mouth of his. And God forbid they’re in another accident together or his heap of a car breaks down and cell phones are beneath him and they’re stranded in the middle of nowhere! How can you let this happen?? He had a black eye. He belongs in jail!

Classic Lorelai, she has taken the phone away from her ear and is now reading the paper.

Mistake #6: Rory goes to Dean rather than having a conversation with Jess.

Does this one really need any commentary? It’s messed up that Rory goes to Doose’s market and only believes that there hasn’t been a fight when Dean tells her. Rory! Who the fuck do you think Dean it?! He is not cool enough to get into fights. (Yeah, yeah, yeah. Violence isn’t cool. I get it.)

Dean-Market-Swan-Song-Gilmore-Girls
You think this floppy-headed motherfucker is getting into fights? Please.

It’s at Luke’s that we finally learn what happens. I love the following scenes with Luke and Jess. I love how Luke handles Jess in the diner. I love how he questions him playfully but then becomes immediately sincere when he sees how upset Jess it. I love how confused he is when Jess tells him to hang up on Rory. I love when he tells Rory that Jess “went somewhere.” Luke handles it just right. He never betrays himself as being on anyone’s side but Jess’s own. He makes clear why he wants to know, and he is supportive even when he finds Jess’s story to be unbelievable.

When Jess runs out to do some “beaking” of his own, Luke goes with him and apparently brings a boat to get better positioning to the swan. Then Luke gives Jess some straight talk about his relationship with Rory.

I can’t remember any other scene in the entire series in which Luke smiles so much.

The message obviously sank in, because Jess is totally conciliatory when he sees Rory later that evening. He doesn’t get mad at her for going to Dean instead of to him. (I would have!) He apologizes. He suggests that there will be another dinner at the grandparents. Buuuuuuut then he ends their reconciliation by telling a very stupid lie. Rory is dumber than I could have imagined if she believed that Jess was “throwing a football” with “a buddy.” Jess doesn’t like football! Jess doesn’t have buddies!? But Rory is thirsty and the two of them make out for awhile before Rory tells Jess to “keep thinking what you’re thinking.”

When she gets home, Rory is ready to tell Lorelai all about her lady tingles:

Lorelai: What’s wrong?
Rory: Nothing. Listen.
Lorelai: I’m listening.
Rory: When I said before that I was too busy to think about it... I realized I’m not too busy to think about it.
Lorelai: Think about it?
Rory: It.
Lorelai: Oh. It.
Rory: Nothing’s happened yet. But maybe.
Lorelai: Maybe.
Rory: Maybe with Jess.
Lorelai: With Jess.
Rory: You still want me to tell you everything, right?
Lorelai: Oh yeah. [...] Could you tell me before it [happens]?
Rory: Right before ...?

Mistake #7: Lol. Seriously Rory? Right before?! Smh.

In all seriousness, though, love the end of this episode. In a show where so much dialogue is packed in, the use of silence was very affecting. You can see Lorelai trying so hard to be supportive while being super uncomfortable that her little girl is now a sexual being. I’m sure that is a weird thing to go through as a parent, and Lauren Graham’s quiet expressions of confusion, sadness, and contemplation seem spot on.

Random observations:

  • Is Rory bullet journaling at the kitchen table? Is she ahead of her time?
  • That kiss that Rory gave Jess was not (let me repeat: NOT) worth $5.
  • Have you ever stopped to wonder if Miss Patty’s “show biz” stories are really true? I don’t mean like fabricated because she’s a serial liar; I mean, I think they might have been hallucinations she had while experimenting with drugs in her younger days.
  • Who the hell is that woman playing the piano at Miss Patty’s? Is she a ghost??
  • Does Emily keep comfortable pajamas in an assortment of sizes just in case? Where did Rory’s pajamas come from??
  • I love Ms. Kim: “Who are all these unwashed boys?”