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Where the Road Goes

Summary:

A reimagining of Rory and Jess in the early years, beginning in Season 3. Tutoring sessions, late-night conversations, and the slow realization that the road ahead might not be the one everyone has planned.

Notes:

Just a grad student attempting to write something that isn’t a paper for once. This ended up in script format because that’s how the scenes came to me. Let me know if you like reading in this format or would prefer a more traditional prose style :) Enjoy!

Chapter Text

INT. LUKE'S DINER – DAY
The diner is busy in that familiar Stars Hollow way — coffee cups clinking, low conversation, the smell of bacon and toast in the air. Luke is behind the counter.

LUKE
Hey Kirk. What can I get ya?

KIRK
I’ll have a pastrami sandwich on rye.

LUKE
We're out of rye.

KIRK
Are you sure? I saw Caesar carrying boxes earlier.

LUKE
Those weren't rye boxes.

KIRK
How can you tell?

LUKE
Because I made the order. Pick another bread.

KIRK
I can't.

LUKE
I'm already sorry I asked.

KIRK
My therapist says I should avoid reliving the incident.

LUKE
Fantastic. Now I'm running a diner and a support group.

Rory looks up from her coffee.

RORY
Why is Kirk so particular about bread?

BABETTE
Oh, sugar — it's for Lulu. He read somewhere that rye has romantic properties.

RORY
Romantic properties? 

LORELAI
Not in front of the child, Babette. You’ll scandalize her.

BABETTE
Oh sorry sweetheart. It's also very good for digestion.

RORY
Ew.

LORELAI
Gross.

KIRK
Babette, that was private information!

BABETTE
Honey, everyone heard you and Lulu talking about it last night at Al's.

KIRK
Al's has an intimacy policy!

Stars Hollow. Come for the coffee, stay for the oversharing.

The apartment door upstairs opens. Jess comes down the stairs holding an envelope.

JESS
Hey.

LUKE
Hey.

JESS
Sign this.

LUKE
What is it?

JESS
Report card. Need a signature.

Luke reads it. Sets it down.

LUKE
Jess.

JESS
What?

LUKE
There are E's on this.

JESS
Yup.

LUKE
More than one.

JESS
Allegedly.

LUKE
And there's a W.

JESS
Yeah. Dropped a class.

LUKE
You dropped a class? Don’t I sign that?

JESS
Relax. It’s one class.

LUKE
You should’ve told me. 

JESS
I'm telling you now.

LUKE
By handing me this?

JESS
Thought you'd appreciate the efficiency.

LUKE
What class? 

JESS
Trig.

LUKE
Trigonometry. Don’t you need that?

JESS
I already took trig. In New York.

LUKE
So why were you in the class?

JESS
School didn’t have my transcripts yet. They stuck me in it.

LUKE
And you didn't say anything?

JESS
I figured they'd sort it out.

LUKE
Did they?

JESS
Eventually. But it was past the drop period.

LUKE
So now it’s a W.

JESS
Yup.

LUKE
And you talked to someone?

JESS
I talked to three someones. They said there was nothing they could do.

LUKE
And you didn't think to tell me so I could talk to someone?

JESS
I handled it. Besides, it's public school.

LUKE
What’s that mean?

JESS
Means they’re not exactly rooting for me.

LUKE

Well, they should. I'm going down there.

JESS
Jeez. Can you just sign it? I'm going to be late.

Lorelai stands, grabbing her bag.

LORELAI
Rory, can you get me donuts to go? I've got the Summers coming in from New York, and I need sugar, or else I won’t be able to sit through their three-hour dissertation on the declining quality of artisanal goat cheese.

RORY
On it.

JESS
Two glazed?

RORY
Two glazed, one sprinkles and one maple. To go, please.

JESS
Coming right up.

LUKE
We were talking.

JESS
You were talking. I was standing here looking really patient.

LUKE
Jess—

JESS
What? You need me to sign my own failure? Hand it over.

Rory has gone still at the counter.

RORY
You're failing?

JESS
Define "failing."

RORY
Luke just defined it.

JESS
Luke's an alarmist.

RORY
He said you got E's.

JESS
I'll live.

RORY
Jess.

JESS
Rory.

RORY
You told me everything with school was fine.

JESS
It is fine. Mostly.

RORY
How are you failing? You're one of the smartest people I know.

JESS
That's a pretty low bar.

He slides the donut bag across the counter before she can say anything else.

LORELAI
Rory! Come on, hon!

RORY
Coming!

She takes the bag, still looking at him. He doesn't look away. Rory heads for the door, then glances back once. Jess is still there, report card in Luke's hand.


EXT. STARS HOLLOW – SIDEWALK – DAY
Jess steps out of Doose's and nearly collides with Rory on the sidewalk. He catches himself, hands going immediately into his jacket pockets.

JESS
Hey.

RORY
Hey.

RORY
So. I was thinking.

JESS
Careful. You do that too much and the town council will want to tax it.

RORY
I could help.

JESS
With what?

RORY
School.

JESS
Ah.

RORY
Jess, you're failing.

JESS
Rory—

RORY
You're failing, and I can help.

JESS
It's junior year. You've got your Harvard thing.

RORY
It's your junior year, too. Don't you want to graduate?

JESS
I'll graduate.

RORY
Not if you fail two quarters.

JESS
What?

RORY
I looked it up. If that happens they hold you back for the year. You'd have to repeat it.

JESS
Of course you did.

RORY
Someone had to.

RORY
Jess. This is serious.

JESS
I know.

RORY
Then let me help.

JESS
Why?

RORY
Because I can.

JESS
Last time didn't exactly go great.

RORY
The tutoring part did.

JESS
Sure. The tutoring part.

Rory meets his eyes and holds them.

RORY
That's what this is.

Jess looks away, then back. 

JESS
What about your mom?

RORY
What about her?

JESS
She doesn't exactly light up when she hears my name.

RORY
She'd know I was helping a friend with school.

JESS
A friend. Didn't realize that's how you saw me.

RORY
Jess—

JESS
No, it's fine. We're friends.

RORY
Good. Andrew's, after school?

JESS
You want to study at the bookstore.

RORY
It's quiet.

JESS
It's dead.

RORY
There's a difference.

JESS
Is there?

RORY
Yes.

JESS
Okay. Three o'clock?

RORY
Three o'clock. It's a—

She stops. Half a second.

RORY
A plan. It's a plan.

JESS
Easy there, Tracy Flick.

RORY
More Andrea Zuckerman. But with fewer sweater vests.

JESS
See you then, Andie.

He's already smiling a little.

Rory heads toward the crosswalk without looking back. 


INT. ANDREW'S BOOKSTORE – BACK TABLE – AFTER SCHOOL
The back of Andrew’s is quiet — leaning shelves, warm uneven light, the smell of old paper and maybe coffee. Jess is already there when Rory arrives, notebook open. He looks up when he hears her coming down the aisle.

RORY
Here.

She slides a 1” binder across the table.

JESS
What’s this?

RORY
It's a planner. Don't make fun of it.

JESS
You made me a planner.

RORY
I marked all the important dates for the semester. Due dates, test dates. All color coded.

JESS
How do you know what classes I’m in? 

RORY
Lane mentioned it. 

JESS
Ah.

RORY
She said you’re in all the same classes except third period.

JESS
Yeah not really a band guy. 

RORY 

I figured. 

JESS
So how does this thing work?

RORY 
Red is urgent, blue is standard, green means you're fine.

JESS
How much green is there?

RORY
Not a lot. So. If you need to know when something's due—

JESS
I consult the planner.

RORY
See? You're already getting it.

Jess pulls the planner closer with two fingers.

RORY
Mrs. Fink's assignment. 

JESS
I know the assignment.

RORY
You picked Hills Like White Elephants.

JESS
It fits.

RORY
Sure. Nobody picks it because it fits.

JESS
Most people pick the easy one.

RORY
What's the easy one? 

JESS
The one where the old man is sad about the fish.

RORY
Did you start it?

He reaches into the notebook and slides a few pages across. They're slightly crumpled, written in his close, slanted handwriting. Not notes. Actual prose.Rory smooths the first page and starts reading. She reads it. Reads it again. Sets the page down.

RORY
This is really good.

JESS
Pretty sure Perkins would have notes.

RORY
I don't like that it's good.

Jess shrugs.

RORY
Did you write this in class?

JESS
No.

RORY
Okay. Let's pretend I'm Mrs. Fink. What does the American actually want? 

JESS
Everything. Both ways. 

RORY
That's not an argument. 

JESS
He wants her to agree to something without him having to ask her to give it up.

RORY
She already knows what he's asking.

JESS
Yeah.

RORY
She's just waiting to see if he'll say it.

Rory taps the edge of his paper with her pen. Jess keeps his eyes on the notebook. 

JESS
He doesn't.

RORY
No.

JESS
That's the whole story.

RORY
That's your argument. Now build it.

JESS
That's it?

She makes a few notes on the page and slides it back to him.

RORY
That's it. Thirty minutes. Then we regroup. 

They settle into the quiet, the bookstore doing its usual nothing around them — a page turning somewhere near the front, the faint sound of Andrew counting the cash register.

Rory turns a page. Jess writes. Neither of them looks up.

After a while:

JESS
So when are you telling Dean?

Rory doesn't look up.

RORY
Telling him what?

JESS
That you're doing this.

RORY
I'm helping you with school. There's nothing to tell.

JESS
Right.

He goes back to writing. Rory keeps her eyes on her book, then turns the page.

A bell rings somewhere near the front of the store.

RORY
Thursday too? Same time?

JESS
Sure.

RORY
Tuesday and Thursday. Three o'clock. I'll put it in the planner.

JESS
You have a copy of my planner?

RORY
I made you a copy. I have the master. Yours is a field edition.

JESS
There are multiple planners?

RORY
There are always multiple planners.

Jess closes his notebook and picks up the planner. 

RORY
Tuesday. Three.

JESS
Yeah.

He picks up the planner. Doesn't set it down. Rory smiles, just slightly, and starts repacking her bag. Jess watches her, then looks away.


INT. GILMORE HOUSE – EVENING
The TV is on low. Lorelai is on the couch with takeout and a magazine. Rory comes in through the front door, backpack over one shoulder.

LORELAI
Hey! Important question. Brittany Murphy — 8 Mile or Uptown Girls? Hair-wise.

RORY
Uptown Girls. It's not close.

LORELAI
See, I go back and forth. Uptown Girls is the classic argument, but there's something about the bleach situation in 8 Mile that's very committed.

RORY
It's committed to being a mistake.

LORELAI
Bold take. I respect it.

Rory drops her bag by the door and comes into the room. Lorelai looks up from the TV.

LORELAI
So. How was Paris?

RORY
Good. Productive.

LORELAI
Productive. She let you have snacks this time?

RORY
We had pretzels.

LORELAI
Unsalted?

RORY
Obviously.

LORELAI
That girl sure knows how to party.

Rory opens a cabinet, gets a bowl, pours cereal into it. Stands there with it.

LORELAI
Dean called, by the way. Said he tried your cell.

RORY
Oh. I had it on silent while we were studying.

LORELAI
Yeah, I told him you were studying. He said he'd see you Friday.

RORY
Right. I still have Grandpa's book to return.

LORELAI
I can give it to him if you want.

RORY
That’s ok, I want to hear his thoughts. He annotated the whole thing.

LORELAI
Of course he did. Richard Gilmore has never read anything quietly in his life.

RORY
It's one of his better qualities.

LORELAI
Don't tell him that. He'll annotate more things.

LORELAI
Okay well, I was thinking mani-pedi Saturday but if you want to see Dean—

RORY
I have to study Saturday. Raincheck?

LORELAI
You'll raincheck me, but not Friday night dinner? My father. Using dead

poets to run my daughter's social calendar. First Whitman, who's next?

RORY
He has a copy of Complete Poems by e.e. cummings that looked pretty sinister.

LORELAI
Great, not even punctuation will slow him down.

Lorelai looks at her.

LORELAI
So how many people were in the study group,?

RORY
What?

LORELAI
Study group. Just you and Paris?

RORY
Yeah. Just us.

LORELAI
No Madeline and Louise doing dramatic readings of their notes?

RORY
Nope. Just very boring, very focused studying. You would've hated it.

LORELAI
Hey, I've been a member of the Stars Hollow Historical Society since 1999. Boring and I are practically family.

Rory sits, cereal bowl in hand.

LORELAI
I'm proud of you, you know.

RORY
Mom.

LORELAI
Junior year, Paris, all of it. You're doing good, kid.

Rory looks at the cereal bowl.

RORY
Thanks.

Lorelai goes back to the TV.

LORELAI
Okay. Uptown Girls. Final answer?

RORY
Final answer.

LORELAI
I'm coming around to it.

Rory half-smiles. Stares at the cereal. Doesn't touch it.


INT. EMILY AND RICHARD'S DINING ROOM — FRIDAY NIGHT
Dinner is underway. The table is immaculate. 

EMILY
Lorelai, how is the inn?

LORELAI
Thriving. Stressing. Occasionally on fire, but in a good way.

RICHARD
That is not reassuring.

LORELAI
It’s a charming brand of chaos.

Emily gives Lorelai a long look, then turns to Rory.

EMILY
And you, Rory? Junior year is progressing, I hope.

RORY
It’s going well. Busy, but good.

EMILY
Good. You know, I had tea with Bitty Charleston last week. Her nephew is in the same grade as Rory at Deerfield. She said he finished all his college visits this past summer and has already been scouted for an athletic scholarship.

LORELAI
Wow. Didn’t know anyone in that family broke a sweat. What sport does he play?

EMILY
Badminton.

LORELAI
Badminton.

EMILY
Yes, Lorelai. Badminton. Is there something wrong with that? 

LORELAI
Didn’t know colleges were scouting the backyard barbecue circuit.

RICHARD
Badminton is a fine sport.

LORELAI
Hey, if the burgers are good.

RICHARD
It’s very important to be well-rounded, Lorelai. Plenty of students applying to any college have the grades. But the Ivy League requires something more.

He turns to Rory.

RICHARD
Are you still involved in your extracurriculars?

RORY
I'm on the paper. And I've volunteered at things around Stars Hollow.

RICHARD
Wonderful. That's a start. And you're taking Advanced Placement classes, I assume?

RORY
I am. All but French. I'm not great at French.

EMILY
Oh, Rory. I wish you had mentioned that.

LORELAI
Why, Mom? Does Bitty's nephew speak French?

EMILY
No, but they do have a home in Provence. I could ask Bitty if he'd be willing to talk to Rory.

RICHARD
I could ask at work. I believe Hanlen mentioned his daughter is taking Advanced Placement French this year.

RORY
Oh, that’s okay, really. It's just one class.

RICHARD
It might seem like one class, Rory, but Harvard will take note.

LORELAI
Damn Harvard. Don’t they know teenagers need sleep?

EMILY
Perhaps you can meet with your guidance counselor, Rory. They’re trained to advise on these sorts of matters.

RORY
It's the third week of school.

RICHARD
Good. Which means there's still time.

RORY
Time?

RICHARD
Yes, to modify your schedule.

LORELAI
Rory's schedule is fine, Dad. She doesn’t need to change it up for one class.

RICHARD
Language is currency, Lorelai.

LORELAI
So is sleep.

Richard considers this. Emily sets down her fork.

EMILY
How are your grades? Are you doing well in the honors French class? Would they take issue with you moving up?

RORY
No, I don’t think so…

LORELAI
Mom, if Rory's grades were any more impressive, they'd need their own zip code.

Emily resumes eating. Richard folds his napkin with exactness.

RICHARD
You know, Rory, this year matters. Grades, essays, extracurriculars — college admissions look at all of it. Even the people in your orbit matter, equally if not more than your work.

LORELAI
Ah. We've reached the polite warning portion of the evening. My favorite.

Emily cuts a neat piece of chicken.

EMILY
A young lady must be properly socialized. Are you spending your time with good company outside of school?

RORY
Um… I guess?

EMILY
With whom?

RORY
Lane, mostly. And Paris. Friends from school.

EMILY
Friends can be very distracting.

LORELAI
So can dinner with Grandma, but here we all are.

Rory keeps it light.

RORY
I study with Paris twice a week, after school. And I have a study schedule.

EMILY
Good. Paris is a serious girl.

RICHARD
Yes, she is.

EMILY
I hope your other friends are equally focused.

RICHARD
One hopes.

Lorelai sets down her fork.

LORELAI
Wow. A tag team. I feel like I should be wearing a number.

EMILY
I would hate for you to be distracted by someone who is not serious about the future.

Rory lowers her fork.

RICHARD
Paris is excellent company. She wants to go to Harvard too. Though I'm not sure about Rory's other… friends.

LORELAI
Wow. That was almost subtle.

EMILY
It's a shame to spend time with someone who isn't serious about their future.

Emily looks at Rory for a moment and moves on.

EMILY
Good.

A small silence settles over the table.

LORELAI
All right. Enough future talk. I refuse to eat dessert under this much pressure.

EMILY
We haven't even reached dessert.

LORELAI
Exactly. I'm getting ahead of the trauma.

Richard almost smiles. Emily does not.

RICHARD
Ah, that reminds me. I found something for you, Rory.

EMILY
Richard, we haven’t even finished dinner yet.

RICHARD
It will only take a minute, Emily. Whitman's correspondence with his editors at The Saturday Press. Most people don't know these letters exist.

Rory picks it up carefully.

RORY
Grandpa, how do you have this?

RICHARD
I have my sources. What's instructive isn't the poetry — it's the argument behind it. The man was relentless. Every letter a negotiation, a defense, a refinement. Largely self-educated. No formal training. Just discipline and an absolute refusal to be distracted from what mattered.

LORELAI
(to no one in particular)

So, pie?

Rory doesn't look up.


INT. LORELAI'S JEEP — NIGHT
The town slides past the windows, dark and quiet. Lorelai drives. Rory sits in the passenger seat with the Whitman letters in her lap, not reading them.

LORELAI
So.

RORY
So.

LORELAI
Can I ask you something without you saying “fine”?

RORY
Probably not.

LORELAI
The AP French class. That's a lot on top of everything else.

RORY
I can handle it.

LORELAI
I know you can handle it. That's not what I asked.

RORY
I don't think Moulin Rouge is going to count for college credit, so.

LORELAI
It should. Nicole Kidman works very hard in that movie.

RORY
(small smile)

LORELAI
There it is.

Rory looks out the window.

RORY
She's not wrong about junior year.

LORELAI
I'm just saying they didn’t have to tag-team you like that.

RORY
It was fine, really. They’re just looking out for me.

LORELAI
Rory.

RORY
What?

LORELAI
You're allowed to say it was a lot.

RORY
It was a lot.

LORELAI
Thank you. Was that so hard?

RORY
(small)

Little bit.

Lorelai glances over at her, then back at the road. 

LORELAI
Okay. Home. Movie. Something with absolutely no college application subtext whatsoever.

RORY
Is it okay if we call it a night?

LORELAI
You sure?

RORY
Yeah. Movie tomorrow night?

LORELAI
Okay. Tomorrow night, double screening of Ferris Bueller’s Day Off.

RORY
Perfect.

The Jeep turns onto their street. Rory finally looks down at the Whitman letters in her lap, runs a thumb along the spine.

Lorelai pulls into the driveway.


INT. GILMORE HOUSE — CONTINUOUS
The front door closes.  Lorelai has already disappeared upstairs.

Rory stands in the middle of the living room for a second. Her bag is by the door. Her books are on the coffee table. 

She picks up the Whitman letters. Puts on her coat.


EXT. STARS HOLLOW — NIGHT
Gazebo lit, sidewalks empty, the quiet of a Friday that's already put itself to bed. Rory walks without a destination, the Whitman letters under her arm.

She ends up at the bridge.

Jess is already there, leaning on the railing with a paperback open, reading by the light that spills from the streetlamp. He looks up when he hears her footsteps.

JESS
Gilmore.

RORY
(stopping)
What are you doing here?

JESS
Reading. You?

RORY
Walking.

JESS
At eleven on a Friday.

RORY
I needed air.

He watches her, then glances back at his book. She moves to the railing a few feet away.

RORY
My grandfather gave me these tonight.

She holds up the Whitman letters. Jess glances over.

JESS
The correspondence?

RORY
You know them?

JESS
Yeah. I've heard of them.

RORY
He gave this whole speech. Whitman was self-educated, disciplined. Refused to be distracted from what mattered.

JESS
Sounds like a Richard Gilmore conversation.

RORY
It was. And it worked. It always works. He does it with books so I can't even be annoyed about it.

Jess closes his paperback.

RORY
Except Whitman didn't go to Yale.

JESS
No. He didn't.

RORY
He traveled. Worked on newspapers. Talked to people.
Actually saw things.

She looks out at the water.

RORY
I think about that sometimes. Just going somewhere. Before all of it.

JESS
All of what?

RORY
The plan. The whole thing everyone already has mapped out.

JESS
Yeah.

RORY
There are schools with better journalism programs than Harvard.

Jess glances over.

RORY
Real ones. Where you actually write.

I'm not saying I wouldn't go to Harvard.

JESS
But.

RORY
But there's probably more than one way to get where I want to go.

She turns the Whitman letters in her hands.

RORY
Maybe a year somewhere. Before all the deciding gets done for me.

A small silence.

RORY
I can't say that to my mom.

Jess nods once.

RORY
Everything she's done — Chilton, the dinners — all of it points at one thing.

RORY
If I said I wanted to disappear for a year and just read things she'd smile and say great… and then lie awake for a week.

JESS
Probably.

RORY
So I just keep being… fine.

On track. Quiet.

The creek moves under the bridge.

RORY
When you're the one who's supposed to have a plan…people kind of assume you always will.

She stops.

RORY
I've never said any of that out loud before.

Jess shrugs lightly.

JESS
Whitman walked from Camden to Washington. Took him three days.

RORY

That's not an answer.

JESS

Wasn't a question.

Rory exhales.

RORY
So what are you doing out here?

JESS
Reading.

RORY
At eleven. On a bridge.

JESS
Stars Hollow's not exactly overflowing with options.

RORY

You could've read at the apartment.

Jess looks back down at the water.

JESS
Needed air.

RORY
Luke?

JESS
Just… stuff.

She nods. 

Rory glances at the book in his hand.

RORY
What are you reading?

Jess turns it over. Travels with Charley. Rory studies the cover.

RORY
How is it?

JESS
Good. He just goes. No plan. Just the road and whatever's next.

RORY
Read me something.

Jess looks at her. She settles against the railing. He opens the book. Jess starts reading. The streetlamp hums softly above them.