Just a oneshot based on a headcanon I have where Jess sneaks into Richard's study to see the painting of Rory, after going to see her in Balalaikas. Hope you enjoy it!
He lets himself out. He runs down the stairs on tiptoe, hands in his pocket, the Gilmore mansion in gloom. He never expected to be here again. It's been three years since he was here but the place seems the same, even in the shroud of night. The house is the same but the girl has changed.
Jess doesn't make a sound on the staircase, despite its age and creaks. He's used to quick exits, making no noise in the dark. It's unconscious now, this ability. He runs down the last few steps before landing in the hall. He's moments from the door, his hand already stretched out, when he stops. He turns, looks to the left. The study.
Jess pauses for less than a second before going to it. He's only going to take a look. Carefully, silently, he twists his hand around the handle, pushes open the door and slips in. He knows it's there before he even turns on the light.
Rory sits above him in oil form. Young and decked out in a fanciful dress, she sits staring into the distance, book in hand. Jess swallows. There she is, seventeen or thereabouts, with no sadness clouding her eyes. No fear as she glances into her future.
Rory, what's happened to you? Fuck. She was the one in control. She was the one who knew where she was going, what she was doing, had planned each step. She was so determined, so smart. She made him want to do better. She made him do better. He couldn't have written this book without her pushing him, her words in his mind.
What the hell has happened? Living with her grandparents, dropping out of Yale...it's all just temporary, he hears her say. Rory, don't lie to me. You're pretending. I can see it, I can always see when you're lying or being fake. What the fuck has happened to have changed the Rory he remembers into the scared girl upstairs? It has to be more than one thing.
Jess settles down onto a chair. He hadn't planned on staying for more than a minute but his thoughts are weighing on his mind. He knows Rory is scared, he knows this is some kind of act. Rory would never take a little time from college, not unless something drastic has happened. Rory talked about going to college the whole time he knew her. Okay, so it was Harvard and now it's Yale, but it's the same gist. It's one of the top schools in the country. Rory's been planning it her whole life, she has to go to college. She has be Christiane Amanpour. Jess smiles to himself but it soon fades. He knows something has happened, something bad. For one thing she's stopped speaking to Lorelai. Luke didn't allude to much but he didn't need to. While Jess always thought maybe she cared too much about her mother thought, this is too far. He guesses it's over this, over not going to school and he rubs his knuckles into his brow. What is going on?
Jess opens his eyes and looks back up at the painting. The time he first saw it is clear in his memory. He'd come over to please her grandparents – like that was ever going to happen – and fought with Rory. Okay, so he'd been a dick to her grandmother, but he could see what she was thinking. He could see what they were all thinking, her grandparents, her mom, even Rory in his worst moments. He's not worth taking to dinner. He has no manners. He was dragged up. How can he ever be good enough for Rory next to precious fucking Dean? They as good as said it. He was only living up to their expectations. Jess shakes his head as their young faces emerge in his mind, like a TV show. She was furious, he'd never seen her so mad, and he was mad too, and frustrated, and pride kept him from blurting out the truth. You want to know how I got this black eye? It was from a bird, okay? It was from a stupid swan. Only I can't tell you because I'll look like a moron and there's no point in telling you because you've already made up your mind!
He wonders what she'd have done if he'd actually said that. He can almost see her expression in his mind, the shocked eyes, the mouth starting to open. Maybe he should have said it. But he didn't. He'd had enough and he drove away, half expecting never to see her again. They made up, wonderfully made up, but the outcome was the same. He left. He never told her the truth. He didn't think he was enough for her.
Now it's like some kind of crazy mirror house, where everything is distorted and upside down. He's got it together. Okay, it's not the Ritz, more a group of guys crammed into a small apartment, but it's a business. He's written a book, he's published a book. Jess Mariano is an author. He's stopped – what did she call it – shaking it around. What's happened to Rory Gilmore? She isn't studying, isn't about to graduate. She doesn't have plans to become a foreign correspondent. She doesn't have plans for anything. She's living with Richard and Emily and planning out DAR functions. She isn't speaking to her mother. She's living in a bedroom designed for a fifty-year-old and wearing clothes picked out by her grandmother. Is there a guy? Rory hasn't mentioned anyone but Jess wonders, suspects there's a boyfriend who fits her grandmother's bill. It wouldn't surprise him. Does she talk about books with him? Jess doubts it. He hasn't met him but has a pretty good idea all the same. An image draws in his mind, a blurred watercolour of a preppy Yale boy.
As Jess ponders this another memory slips in, the night he and Rory slid across the snow in the sleigh. He asked what she talked with Dean about. Rory shifted, looked uncertain and got defensive. Lots of things. She couldn't name one. Even after they broke up, he was on her mind, on everyone's mind. God, how he hated that jerk. Dean, the golden boy of Stars Hollow, who could never do anything wrong, a regular boy scout. He knew better. Rory was scared of him. She lost his bracelet – with his help – and when she saw she was afraid to tell Dean. It wasn't her fault. She said Dean wouldn't see it that way. She talked about him like he was her prison guard, not her boyfriend. She practically pushed Jess out of the house that night Dean came over, when he had dinner with her and Paris, and Dean acted like he'd found them in bed. No one else ever saw a bad side to Dean, no one believed there was one. There was no point trying to tell anyone that, they wouldn't believe him, even Rory didn't. Jess suspects his uncle dislikes Dean, he's seen his sneer when Dean is there, but he told Jess to leave him and Rory alone. Jess didn't. Okay, he'd stirred up some trouble but Dean was a jerk. He didn't know Dean was going to humiliate Rory in front of everyone, at that stupid contest, and even though he'd been mad at her, for kissing him and pretending it didn't happen, Jess realised he'd forgiven her awhile ago. She didn't deserve that. And then Dean pretended he wanted to be friends with her, trying to threaten Jess, and he was constantly hanging around like mould. Jess remembers going to see Rory, asking her to leave with him, and Dean being there. It was a shock and lack of surprise all at the same time. It figured. He was always at her heels. Always there with his stupid smirk. Everyone was so quick to remind Jess he couldn't measure up.
She is over you. Jess remembers Lorelai's scowl, the venom in her words. She never stopped hating him. She didn't want to. Jess knows they didn't get off to the greatest start, but he couldn't take it, the way she acted like all he needed was a pat on the back and a smile, like she knew everything about him, and how Luke was such a great guy. What did she know? Nothing. Sometimes Jess thinks he and Lorelai could be friends, or at least tolerate each other – he didn't mind the small talk in her kitchen and he enjoyed sharing a joke with her at Luke's expense – but she'd always be mad at him for something, and not just because he never changed the water bottle. She'll never give him a second chance. She'll never forgive him for loving her daughter. He remembers how she yelled at him for hurting Luke. She was right to be mad at him for that, but Jess couldn't explain, and why would she listen? How could he tell her he was mad because he'd let Luke down, the one family member who'd given him a chance? That he was mad at Luke for thinking anything with him and Liz could change? He was tired of Luke trying to fix them, because he got disappointed. But even as he thought it he was waysided by Lorelai going off about leaving Rory alone, that she was over him. If she's so over me, he wanted to say, why do you have to keep saying it? Do you think loving her was a joke? It's killing me. Of course he didn't say that. Instead he scowled back and thought about how she wasn't one to be lecturing him about love. She was clearly still in love with Luke. They were so into each other it was painful. It was as if they were the teenagers. Jess can't remember the number of times he teased his uncle, asking why he didn't just ask Lorelai out. What was he so afraid of? Lorelai got a dopey look in her eyes whenever she mentioned him, she was hardly going to turn him down. Luke would usually bark at him to mind his own business but sometimes he'd hesitate, look ready to talk. Then he'd shake his head, change the subject, tell Jess to get back to work. Both of them hung up on the Gilmores. Now it seems it has worked out for Luke, at last, and Jess is thinking about Rory.
He remembers the night in the car, the night of the accident. How well it was going beforehand. Just talking without all this stupid pressure; from her mom, from Dean, from Luke, from the whole insipid town. The way Rory laughed out loud, how she smiled so widely, how he couldn't help smiling too. It lit up her whole face and made her look beautiful. And she wasn't worrying about Lorelai or Dean or how they should be studying and was just happy. And then she turned to him and said he could do more, that he was stronger than that. He made a joke but the words went to heart. No one had ever said that before. No one ever said he was smart, capable, could do more than blow off class and pull pranks. He'd stopped thinking it himself. Jess knew he was smart enough to do the work in class, he read twice as much as anyone else there, but he never thought he could do more. No one had ever had such firm, unwavering faith in him. All he did was disappoint people, or show them not to get their hopes up in the first place. Most of them already had none. Everyone had hopes for Rory. Everyone knew she would be fine. If someone had told Jess four years from then he'd have written a book and she'd have left college he'd had laughed, refused to believe it. It would be a crazy joke. This is a crazy joke. What has happened in the two years since he saw her last?
Jess doesn't blame her for saying no, that night he asked her to leave. It was a stupid thing to do, a stupid thing to ask. He hadn't gone there meaning to ask that, beg her to run away with him. God, he just wanted to talk, figure things out. He panicked when he saw Dean, forgot everything he was going to say. The only thing he did mean was telling Rory he loved her, and knowing she loved him. When she told him she didn't it hurt worse than anything anyone else had ever said to him. Worse than when he was told he had to move to Stars Hollow. Worse than when Rory said goodbye to him when he kept calling and losing his nerve. Worse than when Luke told him he had to leave. He couldn't face the look in Rory's eyes. Jess remembers turning away, not saying a word, and when he was in his car, back on the way to New York, tears fell. He let them dry there, not bothering to wipe them off. He deliberately stayed away afterwards . He didn't want to see her until he'd figured himself out. He's figured things out and Rory's life has come unravelled. Luke doesn't know why and if he does, he isn't saying. Jess wants to shake his uncle. What is going on with Rory? Sometimes it seems everyone around her thinks she's made of china, incapable of protecting herself. Incapable of making a mistake. Rory's capable, she's capable of so much more than they give her credit for, yet half the time they act like she's a little kid, for all they say she's so smart. They act like he corrupted her, but she was the one who wanted to drive on, the one who took a bus to see him in New York. She has an irresponsible side and they refuse to see it. Rory's capable of screwing up and somehow she's got herself into this mess. She's capable of getting out of it, but she's not. She's sitting firmly in denial. It's something other people can't fix for her so they're ignoring it. Why isn't anyone doing anything about it, making her talk? Jess wants to go back upstairs, go to her and start talking, just him and her. He wants to sit beside her and look into her eyes.
Jess doesn't, though. Instead he takes a long, lingering look at the painting. He imagines the two of them sitting alone, away from everyone else, like all those years ago. You could do more he says silently and then smiles. It's his turn to say it. He will see her tomorrow, talk about it then. Tomorrow. It gleams in the distance, a will'o'the wisp. He's so thrilled at the thought of going out with Rory, without having to whisper, pretend to anyone. He's excited but it's dimmed with the worry he has. He won't let it slide. He's going to help her like she helped him. He's going to find out what happened.
Tomorrow they'll go out, find their own piece of the city. They'll eat somewhere that's not pretentious, somewhere which her grandparents wouldn't approve of and they'll talk. It doesn't have to be anything more. He'll listen, let her know she doesn't have to pretend with him, act like she's happy when she's not. Tell her she's made a mistake but she can fix it. Tell her he's there, if she wants him to be. He probably won't say it as eloquently, probably they'll get mad, but Jess doesn't care. Seeing Rory is what matters.
Jess gets up from the chair, stretching. He goes to the door, not making a sound, and glances back at the picture. The girl is staring into the distance, young and sure of herself. The Rory he remembers is still there in the young woman upstairs. He's confused and worried and mad at her, but he's going to help her figure this out, like she helped him. He's missed her, he couldn't be where he is now without her. He loved her. Jess doesn't know if he still does, but he knows he could. He was nervous to see her but it didn't feel strange. Those old feelings are there. They're older now, and different, but they still have that connection, that spark. He can feel it, taste it. If she kissed him he wouldn't resist. He still yearns to put his arms around her, nestle her close. Maybe they'll fall back in love, maybe they won't, but he's still there for her. Maybe they'll talk about other things they remember, stuff from when they're kids. He remembers how those days in Stars Hollow seemed to stretch out endlessly, that there never felt like there'd be a time when they weren't hiding from chaperones and making out on the couch. How he thinks a lot about their day out in New York, and how he's never stopped searching for Belinda, and she'll know what he means. He won't tell her about how whenever he's in New York he sits on their bench, hoping she'll come. He won't mention all the letters he wrote and tore up. He'll wish her a happy birthday. He'll tell the truth about the swan, see her laugh – Jess would love to see her throw back her head and laugh again. It looks like she hasn't done so in a long time. She smiled but still looked sad. Jess can see it. They can talk about everything, they'll have all night.
Jess finally exits the room, switching off the light. There's not a sound, no stir from above, for all the grandmother being a light sleeper and Jess creeps out of the house, carefully closing the heavy front door. He goes over to the gate and looks back at Rory's window. The light is on and he knows she's awake, reading his book. He smiles. He came here to tell her he couldn't do it without her. He has to tell her she can do it, too. She will. After all, he knows her better than anyone.