What if Jess' Gilmore Girls Spinoff Happened? Windward Circle Episode 2

INT. BOOKSTORE BACKROOM - DAY

Jess is buried in a mountain of used books, each more dog-eared than the last, when Jimmy breezes in, brandishing two cups of coffee like trophies.

JIMMY

(grinning)

Thought you could use a little 'bean' there, done that. Black, one sugar, right?

JESS

(surprised, chuckling)

Uh, yeah. Thanks. Didn't take you for the barista spy type.

Jimmy hands him the coffee and leans against a shelf, trying to look casual but ending up more like a misplaced bookmark.

JIMMY

So, how's the great book shuffle of 2024 going? Sasha's been singing your praises out there.

JESS

(shrugs)

It's fine. Just shelving books—it's not exactly rocket science or even bottle rocket science.

JIMMY

Still, it's good honest work. Beats being a professional yo-yo tester.

An awkward beat. Jimmy notices the book in Jess's hand - “The Dharma Bums.”

JIMMY (CONT'D)

(points to the book)

Hey, I love that one. Must've read it a dozen times.

JESS

(skeptical)

Really? Doesn't seem like your kind of thing.

JIMMY

Why, because I don't look like a literary type?

JESS

(smirks)

More because you seem like you couldn't sit still long enough to read a cereal box without.. (trails off) ..multitasking.

JIMMY

(chuckles)

Fair enough. But seriously, that book was is like comfort food for my soul. The main guy, Ray, talking about feeling lost, out of place... it's like he's reading my mail.

Jess looks at Jimmy, seeing him in a new light.

JESS

Yeah, I get that. Words can do that... make you feel found.

JIMMY

You know, I once fancied myself the next great American novelist. Thought I'd be the next Burroughs or something, ended up more Bukowski-lite.

JESS

(curious)

What happened?

JIMMY

(shrugs)

Life happened. Realized I was better at running from my problems than writing about them. But you... you've got something, Jess. The way you talk about books..

Jess shifts uncomfortably, not used to such praise.

JESS

(deflecting)

Yeah, well, fat lot of good it's done me so far. (goes to head to the register) Couldn't even finish high school.

JIMMY

(firmly stops him with his words)

Hey, don't do that. Don't short-change yourself. You're smarter than you think, smarter than I ever was. Don't let anyone—especially yourself—tell you different.

A beat as Jess absorbs this, torn between hope and doubt.

JESS

(changing the subject)

I should get back out there. Sasha's probably mounted a search party by now.

JIMMY

(nods)

Right, of course. I’ll let you escape the book fort.

Jess starts to leave, then pauses.

JESS

(sincere)

Thanks. For the coffee and... you know. The pep talk.

JIMMY

(smiles)

Anytime. That's what (starts to say dad’s) - friends are for—coffee and unsolicited advice.

As Jess does his fast dual eyebrow raise, he exits, Jimmy picks up “The Dharma Bums," running his hand over the worn cover, lost in thought.

JIMMY

(staring out)

Friend, huh… Always sabotaging the moment.

FADE OUT.

END OF ACT TWO

INT. BOOKSTORE BACKROOM - CONTINUOUS

Jimmy watches Jess leave, a blend of admiration and concern etching his features. He fingers the pages of the book his gaze distant and contemplative. The door swings open, and Sasha bursts in with the energy of a screwball comedy heroine.

SASHA

(cheerfully exuberant)

Hah! Caught you red-handed, huh? Wait this isn’t the warlock and fairy smut section, you’re actually reading something?

JIMMY

(jolting back to reality, grinning)

Just taking a trip down memory lane. You know, the local paper review my characters had a place somewhere between Fitzgerald’s lost generation and Salinger’s brooding youths.

SASHA

(leaning in, humoring him)

Isn’t that the one with the existential crises that would give Woody Allen a run for his money?

JIMMY

(chuckling)

Exactly. It’s like if Holden Caulfield and Rick Blaine decided to open a bookstore in Casablanca.

JIMMY

(raising an eyebrow, playful, looking at her book)

Rand? That’s quite the leap from your usual diet of wayward damsels in distress and alcoholic detectives in true crime sagas.

SASHA

(nodding, holding up a book)

Actually, yes. “The Fountainhead.” I know she’s a bit controversial, but Jess was telling me about the girl who made him read it.

JIMMY

Don’t get me started.

SASHA

(shrugging)

Plus I’m always expanding my range and prepping for trivia night! Speaking of which, you joining us this Thursday?

JIMMY

(thinking)

I might just do that. Could use a fun night out.

SASHA

(grinning)

Great! It's settled then. Oh, and bring Jess along. He could use some cheering up, looks like he’s carrying the world on his shoulders.

Jimmy nods, his gaze drifting back to the book in his hands as Sasha exits with a wave. Alone again, he flips through the Kerouac one more time before placing it gently on the shelf, a resolute look forming on his face.

JIMMY

(softly, to himself)

Maybe it’s time to start writing again.

INT. BILL'S PUB - NIGHT

The pub is abuzz with the competitive energy of trivia night. Teams huddle at their tables, strategizing over steaming cups of coffee and plates of half-eaten nachos. Bill, the evening's unyieldingly stern quizmaster, brandishes a stack of trivia cards like a blackjack dealer at a high-stakes table.

BILL (booming) Alright, quiet down! No cheating, no Googling, and definitely no phoning a friend, unless it's Ghostbusters for your paranormal inquiries. Let's get rolling. First category: Obscure Films.

The crowd's excitement bubbles over like a shaken soda, tinged with nervous anticipation. At one table, Jess, Jimmy, and Sasha—dubbed the "Literati Legends"—share a look of determined trepidation.

SASHA (elbowing Jess) Ready to flex those cinephile muscles? I didn't binge watch the Criterion Collection for nothing.

JESS (smirking) As ready as Sisyphus before his boulder-pushing routine. Let's make Tarkovsky proud.

JIMMY (chuckling nervously) Already making my brain hurt.

Across the room, their rivals, a quirky trio known as "Manic Pixie Nightmare," each sporting vibrant blue and purple hair and two with bedazzled ukuleles strapped to their backs, give off an air of eclectic charm. They are the quintessential manic pixie dream girl bookworms, known for their whimsical attire and lightning-fast recall of literary trivia.

BILL Question one: In Andrei Tarkovsky's 1979 science fiction film "Stalker," what is the name of the mysterious, forbidden zone the characters explore?

JIMMY (whispering to Jess) Tarkovsky? I thought this was supposed to be about movies, not Russian literature.

JESS (thinking hard) It's... it's... The Zone. They just call it The Zone.

Sasha scribbles down the answer, her pen hesitating slightly.

BILL Next question: What is the title of Maya Deren's influential 1944 avant-garde short film, often cited as a seminal work of American experimental cinema?

The trio exchanges blank looks. Jess's mind races.

JESS (mumbling) Deren... Deren... I know this... It's right there...

SASHA (snapping her fingers) "Meshes of the Afternoon"! I remember reading about it in that obscure film journal.

As they jot down their answer, adrenaline surges through them, mixed with a healthy dose of self-doubt.

BILL Last question for this round: In Béla Tarr's 1994 epic "Sátántangó," how many shots is the film composed of?

A palpable sense of unease settles over the Literati Legends.

JIMMY (whispering) Shots? Like, camera shots? Who counts those?

JESS (wracking his brain) It's a famously long film but these really long and still shots I remember reading something about its unconventional structure... 160 or 150, lets go 150

SASHA (uncertain) That sounds... plausible? Let's go with it.

Cheers as the bell signals correct.

MONTAGE

As the rounds progress, tension builds. "Manic Pixie Nightmares" seems equally stymied by the esoteric questions, their earlier confidence replaced by furrowed brows.

INT. BILL'S PUB - NIGHT

As the trivia night tension mounts, Jess squints across the room at the MPN table, where a familiar face sends his memory scrambling. He nudges Jimmy and Sasha, his voice a low whisper.

JESS

(whispering)

Hey, isn't that the girl from the bookstore earlier? The one who dropped a Howl reference like it was hot?

SASHA

(peering over, curious)

The cute one with the glasses? Yeah, that’s her. Zelda, wasn't it? Quite the literary flair she had.

JIMMY

(grinning)

Well, well, well. Looks like your heart might have some competition too, Jess—both in love and literary trivia.

Across the room, Zelda catches Jess's eye, and a subtle exchange of recognition flits between them, underscored by a coy smile.

ZELDA

(to her teammates, amused)

That's the guy from the bookstore. The one who actually knew who Ginsberg was without a Google assist.

QUIRKY TEAMMATE #1

(chuckling)

Looks like you’ve got a literary crush, Z. Let’s hope he doesn’t out-trivia us or flood our mind with swooning looking at Zelda.

QUIRKY TEAMMATE #2

(smirking)

Yeah, fraternizing with the enemy? Scandalous, especially if he has a better bookshelf.

ZELDA

(rolling her eyes, focused)

Focus, team. We've got a title to claim, and it’s not ‘Most Distracted by Cute Bookworms’.

(lost and staring at Jess, daydreaming)

..And one of us has a boyfriend.

Back at the Literati Legends' table, Jimmy relishes the unfolding drama with some playful ribbing.

JIMMY

(teasing Jess)

So, Jess, planning to ask her out after we demolish her team? Or are you worried she’ll quote Shakespeare better than you?

JESS

(scoffing)

Please, I’m too busy strategizing our win to script romantic comedies here.

SASHA

(grinning)

Sure, because figuring out the shot count in a Hungarian film is much more joie de vivre.

JESS

(smirking)

Exactly. Priorities, right?

The final question looms large as Bill gathers everyone's attention with a dramatic flair only he can muster.

BILL

And now, for all the marbles: In Rainer Werner Fassbinder's 1974 film "Ali: Fear Eats the Soul," what is the occupation of the protagonist, Emmi?

Silence blankets the room, each team member mentally digging through their film knowledge. Jess, Jimmy, and Sasha lean in close, the weight of the question pressing down.

JIMMY

(whispering)

Fassbinder... Fassbinder... It’s on the tip of my tongue, but...

SASHA

(biting her lip, anxious)

Drawing a total blank here. Jess, any light bulbs flashing?

JESS

(straining, hopeful)

I think she was a cleaning lady. Yeah, she cleaned apartments, right in the heart of Munich’s drama.

Sasha hurriedly scribbles their final answer as Bill announces the time is up. The pub collectively holds its breath, the suspense as thick as one of Tolkien’s novels.

BILL

(dramatically)

And the winners, by a mere half point... are the Literati Legends!

Cheers explode around them like a New Year's Eve party. Jess, Jimmy, and Sasha embrace, a cocktail of relief and disbelief in their eyes.

JIMMY (to Jess, chuckling) I have no idea how we pulled that off. I feel like I just survived a David Lynch film.

SASHA (smirking) At least we didn't have to decipher any backwards-talking this time.

JESS (grinning) Next time, let's stick to something a little more accessible. Like quantum physics or ancient Sumerian literature.

Over at Manic Pixie Nightmare table, Zelda gives a good-natured shake of her head, accepting defeat gracefully and steals a glance.

ZELDA

(to her teammates)

Well, beaten by bookstore nerds. There’s a plot twist for you. They should handicap them

QUIRKY TEAMMATE #1

(shrugging)

Hey, at least we lost to a worthy opponent. That Jess knows his Fassbinder.

QUIRKY TEAMMATE #2

(nudging Zelda)

Go on, Z. Offer your congratulations. Maybe swap a few poetic verses?

ZELDA

(laughing)

Oh, stop. But... maybe I will say hi. For the sake of good sportsmanship, of course.

As Zelda approaches, Jess looks up, his victory glow mingling with a flicker of anticipation. Jimmy and Sasha exchange knowing grins, their eyes dancing with mischief and amusement.

ZELDA
(teasing)
Well, well, well, if it isn't the Literati Legends themselves. Basking in the glow of victory, are we? Bravo, Jess, bravo.

JESS
(smirking)
Thanks, Zelda. Turns out all those late nights with French New Wave cinema weren't for nothing.

ZELDA
(raising an eyebrow)
Impressive. And here I thought you were just another handsome face with a penchant for Kerouac.

JESS
(feigning shock)
Oh, I assure you, my literary bad habits are very diverse.

ZELDA
(laughing)
I can see that. As much as it stings to lose, you've clearly earned it. How about I buy the victor a consolation drink?

JESS
(surprised, but pleased)
That sounds like a perfect plot twist. Just let me clue in my team.

Jess turns to Jimmy and Sasha, who are grinning like they've already heard the best joke of the night.

JESS (CONT'D)
(to Jimmy and Sasha)
Hey, guys, Zelda's treating me to a victory drink. I’ll catch up with you later.

JIMMY
(winking)
Just remember, don’t reveal all our secrets!

SASHA
(swats Jimmy playfully)
Let him have some fun, Jimmy. Go on, Jess. Enjoy.

As Jess and Zelda walk toward the bar, Zelda's surfer boyfriend sidles up to her quirky teammates, who has been watching the exchange with a mix of intrigue and irritation.

QUIRKY TEAMMATE #2
(to Surfer Boyfriend)
Seems like Zelda’s found herself a new sparring partner. Not getting any waves of jealousy, are you?

SURFER BOYFRIEND
(grumbling)
It’s just a drink. Doesn't mean anything.

QUIRKY TEAMMATE #2
(shrugging)
Sure, dude. But those two have more sparks than a Fourth of July fireworks show in Marina del Rey .

CUT TO:

INT. BAR - NIGHT

Jess and Zelda are settled at the bar, their drinks in hand. The initial competitiveness has melted into a warm, engaging conversation.

ZELDA
So, Jess, what's a literary savant like you doing in a place like this?

JESS
(chuckling ruefully)
The usual script—chasing dreams, escaping ghosts, and trying to author my next chapter.

ZELDA
(nodding)
Classic tale of the artistic pilgrim. Venice is a sanctuary for the lost and the creative. You picked the right stage.

JESS
(smiling)
Seems like it. It’s a whole different universe from where I grew up.

ZELDA

Well good sir, I’d be lying if I said I didn’t want to know where that is.
JESS
(smirk)

It’s nowhere. (a beat) Ever heard of Stars Hollow?

ZELDA
(eyes widening)
Stars Hollow? Isn't that the town with the annual hay bale maze and the dog that was elected mayor?

JESS
(laughing)
That all sounds correct.

ZELDA
(grinning)
Sounds like it was ripped right out of a storybook. I love places that feel like they’re directed by Wes Anderson.

JESS
(smirking)
Trust me, it's less idyllic when you live it. But, it had its moments.

INT. VENICE BEACH BOARDWALK - DAY

As they stroll along the vibrant Venice Beach Boardwalk, Jess and Zelda are surrounded by a dynamic tapestry of life that pulses with the energy of street performers, local artists, and wandering tourists. The ocean air is scented with a mix of salt and the warm, inviting aroma of food trucks nearby.

ZELDA
(pointing excitedly to a mural exploding with color)
See that? That's a local work. The artist is unhoused but by choice. Every splash of color tells a story.

JESS
(looking at the mural, his face lighting up with a warm smile)
It’s really something, isn’t it? I think I’ve defined it in my mind five times already. Just when you think you’ve figured it out, it surprises you again.

ZELDA

A beautiful mess.

They continue walking, the sound of street musicians filling the air. Zelda's surfer boyfriend appears, his expression clouded with suspicion.

SURFER BOYFRIEND (to Zelda) So, this is where you've been? Hanging out with him?

ZELDA (sighing) We're just talking, Kai. It's not a big deal.

JESS (calmly) Yeah, man. No need to worry. We're just friends.

KAI (scoffing) Friends? Right. I saw how you two were acting last night.

ZELDA (frustrated) Seriously? You're being ridiculous.

JESS (under his breath) Like a bad soap opera.

Kai steps closer to Jess, his posture threatening.

KAI (menacingly) You got something to say, tough guy?

JESS (raising arms to defend his space) Look, I don't want any trouble. Let's just take a step back, okay?

KAI Oh, where’s your seductive smirk now? What’s the matter? Can’t fit your whole existential crisis into a three-line haiku today?"

KAI Do you also wear that tortured artist expression to bed, or is it just for show when you're pretending to write in coffee shops?

ZELDA (to Kai) Stop it! You're acting like a caveman.

KAI (to Zelda) Oh, so you're defending him now? He’s not On the Road, he’s more like ‘Lost in the parking lot.;

Passersby start to take notice of the unfolding drama, their curiosity piqued.

JESS (to Zelda) I should go.

ZELDA (nodding) I'm sorry, Jess. This isn't your fault.

As Jess walks away, Zelda turns to Kai, her expression a mix of anger and disappointment.

ZELDA (to Kai) I can't do this anymore. I'm done with your jealousy and trust issues

KAI (shocked) What? You're breaking up with me?

ZELDA Yes. You know I hate that jealous act. I need someone who believes in me, not someone who starts fights over nothing.

Zelda walks away, leaving Kai standing alone, the weight of his actions sinking in as the boardwalk life continues around him.

Notes;

Sasha's artistic pursuits:

• Sasha's paintings often feature whimsical, Stars Hollow-esque scenes: a unicyclist juggling books outside her store, a dog wearing sunglasses skateboarding down the boardwalk, or a quirky couple sharing a giant pretzel on the beach. These imaginative, lighthearted images reflect her ability to find joy and humor in everyday life, a perspective that has helped her overcome past struggles.
• Sasha's music taste is eclectic, ranging from classic rock to indie folk. She's known for her impromptu ukulele performances at The Vinedresser, where she puts her own spin on songs like "Bohemian Rhapsody" or "Wonderwall," much to the delight of customers. These musical moments showcase her creative spirit and help create a warm, welcoming atmosphere in the bookstore.

The bookstore's significance:

• The bookstore hosts a monthly "Literary Costume Party," where attendees dress up as their favorite book characters. Sasha always goes all out with her costumes, once memorably portraying a gender-bent Captain Ahab complete with a stuffed whale sidekick. These events reflect her playful nature and help foster a sense of community among local book lovers.
• Every year on Independent Bookstore Day, Sasha organizes a quirky scavenger hunt around Venice Beach, with clues hidden in books and local landmarks. The grand prize is a year's supply of coffee from the cafe next door, a nod to the Gilmore girls' caffeine obsession. This beloved tradition showcases Sasha's dedication to promoting literacy and supporting local businesses.

Sasha's relationship with Lily:

• Sasha and Lily have a tradition of creating silly, pun-filled songs about their daily lives, such as "Ode to a Tofu Scramble" or "The Ballad of the Lost Left Shoe." These impromptu musical moments showcase their strong bond and shared sense of humor, reminiscent of Lorelai and Rory's witty banter.
• When Lily was struggling to fit in at school, Sasha helped her organize a "Misfit Toy Drive" to collect and donate unique, unconventional toys to children in need. This project, inspired by the Island of Misfit Toys from "Rudolph the Red-Nosed Reindeer," helped Lily embrace her own quirks and taught her the value of accepting others' differences.

Sasha's role as a mentor:

• When Jess is hesitant to share his writing, Sasha sets up an anonymous "Poet Tree" in the bookstore, where customers can hang their original poems or stories from the branches. She encourages Jess to contribute, and his work receives positive feedback, boosting his confidence. This creative approach to mentorship is similar to how Luke secretly bought Lorelai's basket at the charity auction to show his support.
• Sasha introduces Jess to the "Venice Beach Beats," a local writing group that meets weekly at the boardwalk to share their work and engage in impromptu, tortured beat-style poetry performances. This quirky, unconventional writing community helps Jess find his voice and provides a sense of belonging, much like how Rory found her niche at the Yale Daily News.

Sasha's impact on Jimmy:

• When Jimmy is struggling to connect with Jess, Sasha suggests they start a father-son book club. They bond over their shared love of Vonnegut and engage in lively discussions about life, love, and the absurdities of the world. These meetings, often filled with laughter and good-natured debates, help Jimmy and Jess build a stronger relationship.
• Sasha encourages Jimmy to pursue his own creative passions, inspiring him to start a quirky, Venice Beach-themed podcast called "Tales from the Boardwalk." Jimmy interviews colorful local characters and shares amusing anecdotes, with Sasha as his first guest. This project helps Jimmy gain confidence and strengthens his bond with Sasha and the community.

Sasha's own personal growth:

• Despite her progress, Sasha still grapples with imposter syndrome, sometimes doubting her ability to be a good role model for Lily and Jess. She faces these insecurities head-on by joining a support group for single mothers, where she learns to embrace her strengths and imperfections, much like how Lorelai found solace in her conversations with the other mothers at the Gilmore mansion.
• Sasha's fear of commitment and abandonment, rooted in her past experiences, sometimes causes tension in her relationship with Jimmy. She works to overcome these issues by attending couples' therapy sessions that incorporate art and music, allowing them to express their feelings in creative, unconventional ways. This quirky approach to therapy helps Sasha and Jimmy build a stronger, more resilient partnership.