A/N: So sorry for the delay with this chapter! I had to rewrite it about five times and it was a lot harder to write than I thought, soo as always, I'd really appreciate your feedback and reviews!

Chapter 14

Jess wasn't that light of a sleeper, but that particular Wednesday night, he'd had a nightmare about one horrible fight with his mother. It'd been the kind of nightmare he couldn't really fall asleep after, not unless he blasted some metal music, which he'd done several times back at Luke's but figured the Gilmores wouldn't appreciate. His mother's voice screeched in his head, ringing like a bad record on repeat. As he closed his eyes and tried to control his breathing, he became aware of the noise coming from the kitchen. It sounded like a faint banging, drawers opening and shutting, a faint cursing. Thankful for the distraction that was drowning out the yelling in his head, he tiptoed towards the kitchen.

'Rory?' He asked curiously.

Rory jumped, nearly dropping the mug she was carrying. The mug did a little dance in midair, but finally settled back in her palms, making her sigh in relief. The light was dim, the only illumination coming from her bedroom adjacent to the kitchen, and it was casting shadows over her face. She closed her eyes for a moment and said quietly. 'God, Jess, you scared me.'

'You okay?' Jess asked, cocking his head slightly. Rory had seemed somewhat quiet earlier that night. She'd gone to sleep early after dinner, complaining about a headache and claiming she needed to be up early to finish some schoolwork. Lorelai had still been hungover from her meltdown/celebration over the inn's closing, but Jess had noticed that something about Rory's face had seemed off. He knew her well enough by now to know when something was bothering her, even when he didn't know what it was.

She nodded, but her face still had that same tired frown. She tucked a hair strand behind her ear and spoke quietly again. 'I'm making some hot chocolate. I just couldn't sleep and got tired of all the tossing. Did I wake you?'

He tugged at the sleeves of her pajamas, pulling her closer, giving her a small kiss. 'I couldn't sleep either. No coffee?'

'3 am is hot cocoa time, I guess.'

He nodded and caught her lips in another kiss, letting it linger this time and running his fingers lightly down her cheek. He watched the corners of her mouth lift up, but the smile didn't quite reach her eyes.

He nudged his nose against hers, making her faint smile a little brighter. 'You know, I have a great recipe for hot chocolate.'

'Oh, really?' She raised an eyebrow.

'I'm full of surprises, I know.'

'Hot chocolate, you?'

'It's a family recipe.' Technically, that wasn't really a lie. He'd watched Luke make it enough times at the diner.

'Well, you'll have to find the cocoa powder first. I looked everywhere.' She gestured at the kitchen in frustration.

'I think we can manage that.' He said easily, kissing her cheek before turning his attention to the messy kitchen.

'So the jar says chocolate, but you use it to keep…?' Jess asked Rory, sliding his hands up and down her thighs. She was sitting on the counter, while he was standing opposite her, with a great view of her breasts.

'Sugar.' Rory answered, sipping her third cup of hot chocolate.

'Of course. And the sugar jar is for…?' He undid the top button of her pajama shirt.

'Coffee.' She leaned into his touch.

His hand reached down to undo the second button. 'And the coffee jar is for…'

'More coffee.' Rory replied, staring at his fingers and sipping her cup.

'Right, of course. Mislabeling that would just be crazy.' Jess mocked.

He paused to take a sip of Rory's drink, before he deftly got the third button of her shirt open. He was momentarily distracted by her bare skin before he spoke again. 'And the jar that says tea, what's in that?'

'Cinnamon. Sometimes we put some in the coffee.'

'Very fascinating.' Jess shook his head in amusement, dipping his head into the warm skin under her open shirt.

When he ran his lips over the sides of her breasts, she responded with a sharp breath, as her hands came up to knit into his hair and her legs hugged his waist.

He paused to look at her. With his lips still on her warm skin, he said. 'So you wanna tell me what was bothering you before?'

'It's nothing.' Rory smiled weakly, planting small kisses into his hair. Her breath hitched and she hugged him to her tighter, as he started kissing the soft skin between her breasts. With small fast kisses, he made his way up to her collarbone, which he traced with his tongue. Rory shivered as he pressed feather-light kisses against her neck, then sucked on a spot at the base of her neck. She closed her eyes to focus only on the pressure of his lips, making her bare toes curl and her back arch.

When he got to her jaw, he gave her one small kiss and paused. He exhaled and gave her lips a final kiss before he started buttoning her shirt up again, stepping back and laughing at the lustful look on her face.

'Jess!' She pouted, smacking his arm.

'That's how the game goes and it'll keep going till you tell me.' He teased, pecking her lips and stepping back.

'There's nothing to tell. I'm not upset anymore.' She grumbled.

'Nah, I know something's bothering you tonight.'

'I'm fine, really.'

'You're not tired of me, are you?'

'No, no. It's nothing like that.'

'And it wasn't anything I did?'

'No, it wasn't. Now please go back to what you were doing...' She grabbed at his shoulders, sliding him closer.

He nodded seriously, then gave her a half-smile and stepped back again. 'So, the chocolate jar is where you keep the sugar, right?'

'Jess!'

'I can't help it if your kitchen jars are fascinating.' He defended innocently.

'You're a tease.'

'Remind me, the Gilmore sugar jar is for…?' His nose nudged hers.

She rolled her eyes. 'Coffee.'

'And you were upset today because…?'

'Nothing, really, it was nothing.'

'You said you couldn't sleep. What was wrong?'

'I don't wanna talk about it.'

'You'll feel better when you do.'

'Jess, please.'

'Fine. So, we're back to the game then.' He popped her first button open again. 'The coffee jar has…?'

She sighed. 'Coffee.'

'And the tea jar…' He fiddled with the second button, pressing his lips to her neck.

Jess stepped away again, for the fourth time, laughing. 'We'll just keep playing till you either tell me or you relabel all your kitchen jars.'

'Jess!'

'Of course, if you relabel the jars, I'll still find something to mock in your kitchen and the game will just keep going.'

'Stop it!'

'Tell me.'

'Drop it.'

'Rory.'

'Jess.'

'Rory.'

'Fine. I'll tell you,' She put down her fifth cup of hot cocoa and steadied her hands on his shoulders, making him drop his hands to look at her gently. 'If you take me out.'

'Okay.' He agreed easily.

She nodded slowly and looked at him expectantly, her blue eyes piercing his.

'What, you mean now?' Jess chuckled. 'Come on, it's three in the morning.'

'You said you went for walks whenever you're upset. Maybe I should try it too.'

Usually, the walking had been followed by things he wasn't very proud of, but he didn't want to get into that with her. 'That was before. But now, I can say with full confidence that these late-night pajama dates work so much better.'

'It'll cheer me up. Being outside.' She pouted.

'I thought I was doing a pretty good job at that, just a minute ago.'

'You were, but…'

'But what?'

She sighed. 'I wanna rant, but I don't want my mom to hear it. So let's go out, please. The town will be quiet and empty and we won't run into anyone. Doesn't that sound great?'

'I don't know, Rory.'

'I don't wanna go back to sleep.'

'I didn't say we have to sleep.' He smiled suggestively.

'Jess, please.' Her eyes widened at him pleadingly.

'So if we go out for this walk, you'll tell me what's wrong.'

'Yes.'

'Are you just saying that 'cause you're on a sugar high right now?'

'Well, the walk is gonna help with the sugar high.' Her wide eyes fluttered at him.

Rory's puppy eyes made it practically impossible to argue. Jess sighed. 'Fine. Grab your jacket.'

The weather was warm and clear as they walked, arms around each other, in their pajamas through the empty streets of Stars Hollow. Their bridge had a lovely glow to it that night. The dim yellow lamplight reflected on the surface of the water like a mirror and gave the bridge a golden aura. The last time he'd been here was the night they'd first gotten together. He remembered it vividly, Rory's red polka-dot dress and her long eyelashes, how she'd so timidly admitted she liked him, how his heart had nearly stopped, the look on her face when he'd admitted to the same…

He wondered what it was that was bothering her tonight enough that she wouldn't tell Lorelei. And whether it had to do with him. As much as he liked this bridge, he also thought it was the kind of spot Rory would pick if she wanted to break up with him. Were there signs? Had he missed them? Had he done something to hurt her?

Rory interrupted his thoughts as she stepped towards him and wrapped her arms around him. She leaned her weight against him, making him automatically envelope her in tight hug. He guided her head to his shoulder, absently stroking her hair.

She looked up at him and said. 'I really like it here.'

Jess gave her a look, letting her know he knew she was stalling, avoiding what they really came to talk about. 'Yeah, me too.'

'The one spot in Stars Hollow you actually like.'

'It's two spots now. Your bedroom definitely tops the list.'

A slow smile spread over her face as she closed the distance to his lips, kissing him deeply. Her mouth tasted sweet, like the hot chocolate he'd made her, and it made him moan in appreciation. Her lips were doing a lot to calm down his insecure thoughts. They stood there kissing for a long time, neither of them wanting to let go first. Rory was definitely distracting him from the actual talking they were supposed to be doing, but Jess found that he really didn't care. He liked how dizzy his head felt, he liked the noises Rory was making and the way her hands rubbed his back. It seemed that she was drawing strength from their kiss and no way was he going to rush her, not with her kissing him like that.

When they were breathless and panting, Rory stared at him and spoke slowly. 'I found out I was valedictorian today.'

He paused, not anticipating her words. 'You've been upset all night because…'

'They picked me as valedictorian.'

He almost laughed. 'Rory, but that's… Rory, that's so…' great, amazing, wonderful, he wanted to say. He tried not to show the mixture of pride and awe he felt for her at that moment, as her face was still frowning. 'Why is that bad news?'

'Well, for one thing, I'll have to give a speech in front of the whole school.' She said, staring at his chest.

Jess blinked, biting back another laugh. 'So I've been coaxing you into talking for an hour now, because you made valedictorian? Jeez, Rory, I was worried something awful had happened. Like something actually bad…'

She gave him a miserable look, pulling away from him. 'You're right. It's so stupid. I should be happy. I don't know what's wrong with me.'

He sighed, grabbing her hand. 'Okay, let's start over. You're worried about the valedictorian speech, is that it?'

'You're mocking me.' She accused, looking away and running her hands down her hair.

'I'm not. I'm really not.'

'Jess…'

He tried to pull her closer, but she still pulled away. 'Look at me. Just help me understand.'

'It's not just the speech.'

'Then what?'

She replied in frustration. 'I'm already drowning in work. And there's all this pressure to do well on exams. I feel like everyone's expecting so much.'

'But you've always done well, why worry now?' He reasoned.

'I've never had so much pressure on me before. Sure, there was a lot of pressure when I first got into Chilton, but it was just me pushing myself. But now, teachers expect me to know everything or answer questions or do well on papers –' She was pacing in front of him, running her hands through her hair.

'—Which you do.' He interjected.

She went on, ignoring him. '—School is getting so stressful. And if I mess up, everyone's gonna talk about the valedictorian who failed her finals. They'll say I don't deserve it… That I don't deserve to go to Yale or Harvard or anywhere.'

'But, Rory, you already got into Yale. Screw what these people think. You do deserve it. That's all that matters.'

'I feel like… like this is as good as I'll ever get. Most valedictorians don't do so well later in life, you know, Paris said that. I feel like I'm gonna be one of those people that fade out once they get to college. Like this is the best I'm gonna be and then I'll just stumble from there. '

'Paris was just jealous.'

'Well, she wasn't wrong. I looked it up. Most valedictorians are never as successful as they were in school. Maybe they burn out or maybe they only did well in that one environment. I don't know –'

He reassured quietly. 'Rory, that's not gonna happen to you.'

'You can't know that. It's life, it happens to everyone.' She paced back and forth frantically. 'I already feel so exhausted. I've been working non-stop for the past four years and it's exhausting. And I still have four more years to go… And I can't tell that to anyone, especially not to my mom. Not after she gave up so much for me to attend Chilton and get into Harvard and Yale and all these great schools. Not after everything with my grandparents, all the money and the planning.'

'That's why you'll take a break. After your vacation, you'll –'

'I feel so ungrateful. I should be excited and ecstatic and happy… But every time I think about the fact that I'll be starting college next year, I just get so…'

'Scared?'

She nodded miserably.

He stared at her for a long time. There were very few times he'd ever heard her express doubts about the future and he understood why she'd been so hesitant to tell him tonight. What advice could he possibly offer her? While she had an entire school and an entire town pressuring her to succeed, he had everyone in his life expecting him to fail. The irony of him, Jess of all people, giving her career advice wasn't lost on him. In other circumstances, he would've laughed at the sudden role reversal. What did he even know about careers or going to college?

To him, there was no doubt Rory was going to be successful. The force of her stubbornness alone guaranteed it. Her future had always seemed so certain, so planned. And she was the kind of person who not only planned, but followed through on her plans. Still, he was familiar with that feeling of uncertainty about the future. He'd lived through it practically his whole life and he knew better than to downplay how she felt.

He rubbed his mouth, thinking carefully about his next words. 'But would you rather not go to Yale? Would that feel better?'

She considered his words briefly, then shook her head. 'I can't do that to my mom, everyone's expecting–'

'Everyone else, the expectations, the pressure… That shouldn't even come into play.'

'It's not that simple.'

'You're not doing the Yale thing for other people. It's your life, Rory. It should be your choice and yours alone. Just ignore all the pressure, pretend it's background noise, and do your own thing. What is it that you want?'

She looked away uncomfortably.

He drew in a breath. 'Because if you want, we could just leave together. Live in New York or anywhere you want. We could work together, live together, be together. Just travel around, see all the places we talked about. If that's what you want, if that'll make you happy, then that's what we'll do.'

She shook her head imperceptibly. Her eyes bore into his, as her expression changed from shock to disbelief to curiosity. He was pretty sure his face mirrored hers. He hadn't really planned on saying any of that. Where had the words even come from? His mind was reeling, but as soon as the words were out, he knew he meant them completely. He started to wonder if there was a chance she'd say yes. He knew she wouldn't be Rory if she did, but he still couldn't help but wonder.

She closed her eyes and sighed. 'No.' She spoke carefully. 'I can't not go… Not after everything. I wanna go to Yale. I've always wanted to go… I have to do it.'

He shrugged, as though he'd expected nothing else, even as something inside him fell. 'See? There's your answer. You're gonna do great, Rory. Better than great. And you're gonna love every minute of it.'

She buried her face into his shoulders and melted her shaking body against his. He'd never seen her cry before and he was momentarily unsure what to do, his heart beating wildly. He was generally not very good at comforting, so he didn't know what to say. He just held her tighter, rubbing her back and her hair, supporting her petite frame. He could tell he was the only person who saw this side of her, the only one who'd know how scared she really was, the uncertainty behind the perfect façade. As he held her, he understood that she was trusting him with something important. Her vulnerability, this moment of trepidation no one else saw. Everybody loved her because they thought she was perfect, the girl who had it all figured out. But he loved her because she wasn't perfect, because she was real and flawed and so completely inspiring to him.

When she lifted her face to look at him, he took in the tears on her eyelashes, her red cheeks, the way her blue eyes glistened. He wanted to imprint her features in his brain. In all the nights they'd spent together, he'd never felt so close to her, so completely captivated. With her pajamas, tear-rimmed eyes, choked breaths, hands gripping his shirt, he realized he couldn't imagine being anywhere else or with anyone else. The incessant thumping in his chest only proved it further.

'Congratulations. For the valedictorian thing.' He whispered in her ear, when other more important words just wouldn't come out.

She smiled, a genuine smile this time, before her head rubbed against his shoulder again. He just sighed against her, and he couldn't imagine loving anyone more.

A/N: Please review! The prom is coming in a couple of chapters!