Disclaimer: These characters are so not mine. This particular scenario is though.

Thank you to my reviewers:

LitGG1982: Thank you so much for your reviews! I'm so glad you're enjoying my vision of the characters. I hope I will keep it up!
BreathTaker: Here's to attempting to make you an addict! I feel that Jess' character on the show has been left with so much to develop. If ASP won't do it, then I will! Heh.
milofan3150: I'm so happy you enjoy my work. It's really encouraging, especially since this is the first fic I've published.
luvablemilo: Thank you. And you want more Jess? You got him. I think you'll enjoy this chapter.
H0ll3R: Thank you! I'll try my best!
DevilPup9: I'm happy you're happy. If they're in character, it's probably because I've watched the show so much recently, I can practically hear them talking in my head. (It happens when you watch from "Luke Can See Her Face" through the entire fifth season in one night…and morning, for that matter.)
gilmore15girl: Thank you! I usually just write the characters how I hear them in my head (and not in the crazy way, lol), so, even though I know the show really well, a teeny bit OOC is bound to happen at some point. I'm glad you liked the dress part. I had it planned a completely different way, but I like how it turned out.
sanfrangiantsfan: Thank you again! I feel that part of Jess growing up is his emerging ability to be cute if he wants. It doesn't threaten his tough facade anymore. ; )

AN: If only I could be inspired to put as much effort into my schoolwork as I've just put into this story the past 24 hours…Ah well, so anyway…after compulsively checking my stats page to see how many people had read this story (forgive me, it's my first published fic, lol), I decided I was better off putting my energy to productive use. Hence, this chapter; I was also looking forward to some more Rory/Jess interaction, as the last chapters didn't have quite as much as I'd hoped. I think this chapter more than makes up for it. I hope you enjoy reading it as much as I enjoyed writing it.

Grumpy Valentine's Day

Rory squeezed her eyes shut and snuggled deeper into her covers. Maybe if she tried hard enough she could use the Jedi Mind Trick to shut off her alarm without actually getting up.

"…"

Nope, not working. She tried ignoring it, but after a just a few moments the beeping started to grate on her nerves, so she gave in, and hopped out of bed while shutting the alarm off in one swift motion.

"This is going to be one of those days, I can tell," Rory thought out loud.

She stumbled over to the window and pulled back the curtain. What she saw was a steel gray sky, bare trees bending in a strong wind, and cars splashing across wet and slushy pavement.

"Ugh. Perfect, the weather matches my mood," she muttered under her breath.

She changed into her robe and grabbed a towel on her way to take a shower. However, she bumped into Paris in the hallway before she could get there.

"Morning, Gilmore! Sleep well last night? Who was it that you were talking to until so late last night, huh?" Paris asked suggestively while rubbing her hair dry with a towel.

"Paris, you are way too eager for this time of the morning, on this type of morning. None of your business."

Rory pushed past Paris into the bathroom, but swore she heard Paris mutter "Touchy!" before she shut the door. Rory was sure this funky mood of hers was nothing a long, hot shower couldn't cure. Sure, it was Valentine's Day, and she was spending it alone, but that was no reason for her to sulk. However, as she stepped into the shower, she was hit with an icy cold blast, and she began to rethink her previous decision not to sulk.

"Paris!" she yelled as loud as she could. "You used all the hot water!"

All she got in response was a slammed door.

"Fine," Rory muttered angrily to herself.

Rory did her best to tolerate the cold water and finished her shower in record time. By the time she was dressed and her hair was done, she could smell coffee being brewed in the kitchen. The smell was too tempting to ignore, so she followed her nose out her bedroom door and down the hallway.

Paris held out a mug. "Peace offering? I'm sorry I used all the hot water."

Rory sighed, but tried to respond as civilly as possible. After all, Paris did make her coffee.

"It's okay Paris, I'm just in a bad mood this morning and taking a cold shower didn't help much."

Paris nodded and went back to making herself breakfast, all the while humming and sort of bouncing up and down as she moved about the kitchen.

Finally, Rory couldn't help but cave in a little.

"You seem pretty chipper yourself, though."

"Ah, yes. Doyle is taking me out tonight. A real, fancy Valentine's Day date. He won't tell me what we're doing though; he wants it to be a surprise."

Rory felt another wave of grumpiness come over her at the mention of Valentine's Day.

"So, neither he nor I will be home until late tonight. Do you have any plans?"

"I've got a hot date with an article that's due Friday."

"That's it?"

"That's it."

"Oh."

"Oh, what?"

"Nothing, it's just…you've been glued to that phone of yours for almost a week now. I don't know who you're talking to, but I know it's not Lorelai. I just thought it might be a guy. C'mon, Gilmore, spill."

Rory avoided Paris' eyes before answering quietly, "Jess."

"Who?"

"You remember Jess? You met him back in high school."

"That Kerouac and Bukowski worshipping kid…I thought he was a jerk?"

"Well, he's not. He's not a jerk, but he's also not here, and the last thing I want to talk about is Valentine's Day when I'm all by myself."

Rory got up and stomped back to her bedroom. She glanced at the clock; 9:45, her first class didn't start for another forty-five minutes. She found her phone underneath her pillow and called

Jess, even though she knew he would be at work by now. It rang until his voicemail picked up.

"Ugh. Voicemail. Yeah, hi. Sorry, I know you're at work now. I'm just tired from talking last night, and it's gross out today, and Paris used all the hot water, and she's bouncing around the apartment because she's excited it's Valentine's Day and Doyle is taking her on a date, and I don't want to be around her, and I'm in a bad mood, and…I'm rambling. I'm not even sure why I called you. Um, sorry to bother you with all that, I guess I'll talk to you later."

Rory hung up her phone and threw it on the bed in frustration. She hated being in a bad mood, and she wasn't sure how she felt that her first reaction had been to call Jess. She grabbed her backpack, cell phone, and purse and headed out the door, ignoring Paris and Doyle as she swept through the living room and out the door.

By the time she arrived at her 'French: Advanced Culture and Conversation' class, however, she wasn't in a much better mood. She had missed the bus she wanted to take and ended up walking instead. It hadn't helped that a rather large truck had sprayed her with water from a puddle early on in the trip. She was still earlier than usual to class, but there were several of her classmates standing around in the hallway, most conversing in French and correcting each other's grammar.

"Excuse me," she said to the girl who usually sat next to her, "but why is everyone here so early?"

The girl looked at Rory with wide eyes. "Didn't you check your email yesterday?" She almost chuckled when Rory shook her head. "Professor Abiven sent everyone a notice; she's doing an impromptu assessment of the class, a one-on-one conversation with her. She's not sure yet how it will factor into our grades."

The girl turned back to the friend she had been speaking with, and they resumed their practice.

"Crap. This day just isn't getting any better," Rory exclaimed with exasperation.

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Meanwhile, in Philadelphia, Jess was checking his voicemail after getting out of a meeting with his boss. His face lit up when he saw the missed call was Rory, but it quickly fell again when he listened to her message. He hit Rory's speed dial number and waited for her to pick up. He was surprised when she answered but didn't bother saying hello.

"I can't talk now. My French class starts in ten minutes and there's some sort of oral pop-quiz or something. Gah, first all that crap at the apartment, and then I missed the bus, and then I walked to school and got splashed by a truck. And now my professors are out to get me, too. This day just keeps getting worse!"

And with that, the line went dead. Jess stood for a minute in the hallway weighing his options, before knocking on his boss' door.

(0000000000000000000000000000000000000000000000000000000000000000000000000)

Rory's last class ended at 5:20. At 5:21 her cell phone rang, and she was surprised, but relieved, to see JESS on the caller ID.

"Hey," she answered grumpily

"Hi, Rory. Is your day going any better?" Jess asked. Rory's bad mood almost melted a little at the sincerity in his voice.

"Lunch was terrible so I didn't eat much. I don't think I did very well on that French pop-quiz, and then I was too out of it because of French and lunch to concentrate in my 'Gender, Culture & Globalization class, and now in 'Criminality and the Novel' I couldn't stop thinking about you because you're the last person I had a good conversation about Dostoevsky with and I kept wanting to interject, 'Well, Jess would say…'"

"So, I'll take that as a 'no'?"

"And to top it all off, everyone around me is wearing pink or red and carrying around flowers or candy or some ridiculous Valentine."

"Still not in the mood for Valentine's Day, are we?"

"I know, I'm sorry. But if I never see another bouquet of red flowers accompanied by candy and balloons, it will be too soon," Rory finished with a huff.

"Wow, Rory, you're going to challenge Luke for his title of 'Biggest Grump about a Holiday That's Supposed to Make People Happy' if you keep ranting like that."

"Gah! Don't you start in on me, too!"

"Rory," Jess interrupted soothingly, "why don't you go back to your apartment and relax. Do you have a favorite take-out place?"

Rory held out for a moment, not wanting to let go of her bad mood. The idea was tempting though. "Well, yeah. I guess I could really go for some sushi and crispy orange chicken from China 19."

"Okay then, go home, order food, and take a bath or something while you wait for your food to get there. I'm sure you'll find a non-stressful way to spend your evening."

"That does sound good…but, I have work I..."

"Rory. No. Relax. You need it. I can tell, remember? I'm the one who knows you better than anyone else."

Rory took a deep breath and as she let it out slowly, she decided Jess was right.

An hour later, Rory was soaking in a now-lukewarm bath. She had felt the stresses of the day melt away, and now she was left in a much better mood than before. She still wasn't exactly happy, but she couldn't quite place what was wrong. As she stepped out of the tub, put on her robe, and wandered out into her empty apartment, it hit her. She was lonely. She was contemplating calling Jess again, but the doorbell interrupted her thoughts.

"Food!" she cried to her empty apartment. She had to admit she was starving by now.

Rory grabbed her purse and headed for the door, temporarily forgetting she was dressed only in her robe. She opened her door while digging through her purse, saying "Hi, sorry it took me a while to get to the door. How much do I…"

She trailed off as she realized she recognized the delivery man, and not because she had ordered food from the same place too many times.

"Jess. What are you…How did you…Why?" She stumbled over her words in the shock of seeing him so unexpectedly.

He brushed past her into the apartment as he began to explain himself.

"Well, to answer your questions, in order: I'm here delivering your dinner, and mine too by the way; I stopped by the restaurant and told them we decided to pick up the food instead of having it delivered. I'm hoping to keep you company for the evening. I took the train here from Philly after we talked this morning, and before you get too excited, I have work tomorrow, so I'm taking the 12:26 am train back tonight. And as for 'why?'…"

Jess paused, placed the bags down on the counter and turned back towards Rory. He searched out her eyes and when he met them, his face grew serious and he took a few steps closer.

"Altruistically, you needed cheering up. Selfishly, I needed to see you…touch you…to make sure all these late night conversations about you and I…and us…haven't been just dreams."

Rory's heart, after nearly stopping when he showed up at her door, was now racing as he stood in her kitchen. She took a step forward, hesitated, and then crossed the remaining distance between them in a few quick strides. She threw her arms around his waist and buried her head in his shoulder.

He savored the moment of holding her, really holding her, for the first time in what felt like an eternity. He reached his hand up to stroke her hair, but chuckled when he felt that it was wet and cold.

"I see you took my advice. Did it help?"

He felt her nod into his chest, but decided from the way she felt in his arms that he still had a good amount of cheering up to do before the night was over. Suddenly, she backed away, and Jess could see her cheeks turning red as she fiddled with the collar of her robe.

"I'm going to, uh, get dressed now."

He liked that she was still so modest, and that he could make her blush without even trying.

"I'll set up the food, so hurry back before it gets cold."

Ten minutes later, Rory was standing behind the door to her bedroom reaching for the doorknob, but repeatedly pulling her hand back like the knob was on fire. She occasionally would step back to pace across the room a few times before returning to the door to repeat the process.

"This isn't happening. Jess didn't just travel more than three hours to see me when he has to get back for work in the morning. He didn't. He didn't bring me dinner and he's not sitting on my couch. This isn't happening. I can't believe this is happening. Great…and now he's got me talking to myself, too."

Rory spun around once and threw her hands in the air in frustration, then stopped, stared at the door, and took a deep breath. She counted to five as she slowly let the breath out. She was ready now. Rory returned to her living room to find Jess settled comfortably on the couch with the food spread out before him on the coffee table and a movie ready to be played on the TV.

When she didn't come over to the couch, Jess gave her a puzzled look. When she blushed and avoided his gaze, he stood up to talk to her.

"Rory, you agreed to be my Valentine, and since you said you didn't want to see roses, candy, and balloons anymore the rest of your life, I brought take-out, a movie, and myself. I just wanted to cheer you up."

His voice sounded so sincere, Rory's heart almost broke from the strain of hearing it.

"Are you really taking a 12:26 am train back to Philly?" Rory had to speak slowly to keep her vice from shaking. She hoped he didn't notice. She could tell by his reaction that he did. He was looking at her fondly.

"You'd better believe it. I had quite a bit of convincing to do for my boss to let me out early today. Part of the deal is that I'll be back tomorrow, no excuses."

"How long is the train ride?"

"I'll get back to the 30th St. station at about 4:35 am. I should be home by five if I can find a taxi right away."

"And you have work at nine? Jess, you're going to be exhausted!"

He flashed her one of his trademark smirks, and reached out to grab her hand. She found herself being led over to the couch, chopsticks were placed in her hand, and a very serious Jess sat down next to her.

"Rory, I need to know…is Almost Famous okay? I thought, for old times sake…"

He was teasing her. For the first time all day, Rory cracked an actual smile, and his smirk widened into one of his rare lopsided smiles.

"Yes, Almost Famous sounds great."

Rory reached for her food and began to dig in. She and Jess shared the sushi, and she even managed to steal a few pieces of his beef and broccoli, thinking he didn't notice. They really enjoyed the movie: cracking jokes, commenting or mocking when necessary, and singing along to 'Tiny Dancer'. It reminded Rory of that brief period of time in high school when she and Jess were really happy together, and Lane would tease them about acting like an old married couple.

As the credits rolled, Rory turned to Jess and watched him for a moment before he turned to see her. She couldn't help but smile as she watched the light play across his face, now relaxed and smiling slightly from enjoying the end of the movie. She could hardly believe that this happy, considerate, warm man was the same boy who had broken her heart so many times before. He turned and caught her watching him.

"What are you looking at?" he teased.

She reached for the remote and turned off the television, leaving them in a sudden silence. Turning her body on the couch so she was facing him, she looked at him seriously, and then dropped her gaze down to her hands; unintentionally just the actions to really pique his curiosity.

"What is it?"

"So, I was talking to my mom the other day."

"A good thing."

"Yes, a good thing. And I told her a bit about us and how we've been talking."

"I'm not so sure this is a good thing for me anymore."

Rory chuckled slightly, but assured him, "You helped me back to her. She doesn't hate you. She doesn't trust you, but she doesn't hate you."

"Well, at least I have something to work with."

"Yes. So, anyway…She suggested that I ask…well, I'm not really sure if I should bring this up, but I guess I'm curious, too…"

"What is it, Ror?"

"You left. You left after that thing in Kyle's bedroom…and not graduating…and not saying goodbye…and I don't understand."

When Jess sighed deeply and closed his eyes, Rory continued quickly, "I didn't mean to open up old wounds, it's just…I guess I never really understood, and if we're going to…be….together…I need to understand you."

"No, it's okay, Ror. I've wanted to bring it up before, but I was afraid it would be too sore of a subject."

"I want to understand you."

"And I want you to know."

After pausing to collect himself, Jess started his story while staring at a dust bunny in the corner. It was too painful to look her in the eye.

"The day of Kyle's party, I got called into the principle's office when I tried to buy prom tickets. I was told that I had missed too many days to graduate, and that there was no way I could make it up except by repeating the entire year. Now, there was no way I was going to endure another year of that hell, but that was the least of my immediate problems. Since I wasn't graduating, I couldn't buy prom tickets. I felt completely lost, and like a total loser. First off, I'd let Luke down and broken my agreement with him that I could live with him as long as I graduated."

For a moment, Jess paused and looked at Rory.

"Luke was the first person to ever take a genuine interest in me, besides you; he didn't want anything in return but same amount of respect he offered me, he repeatedly refused to give up on me, and now I was supposed to go tell him I wasn't even going to graduate from high school?"

Jess shook his head and then looked at Rory one last time before continuing, first being sure to fix his gaze somewhere safe, like at the scratch in the floorboard by the coffee table.

"And then, seeing you…God, being around you that night was so hard. You are amazing, beautiful, and smart. And I was a complete loser. I was sure Luke was going to kick me out, so soon I was going to be a homeless loser, too. How could I tell you that I wasn't going to take you to prom, and that you were now officially dating a high school dropout? It was too shameful. I couldn't bear to see the disappointment in your eyes. I had seen it before in others too many times, and I think seeing it in yours would have broken down every last reserve of strength that I had."

Jess glanced up when he heard a sniffle from Rory. Big mistake; now he had tears shimmering in his eyes to match hers. Once again he needed to find a safe place for his eyes, especially for this part. Aha, the paint chip on the wall in the corner would do.

"At Kyle's party, things just got worse. You were trying to be a good girlfriend and comfort me, but I didn't want your comfort. I felt I didn't deserve it, just like I didn't deserve you. I wanted to make you understand that I wasn't worthy of you, so you would stop wasting your time on me, and so I could go on with my life and blame you for giving up on me."

"Oh, Jess. If you had only told me! I would've understood!..."

Rory now had tears streaming down her face, but Jess determinedly kept his gaze focused in the corner of the room.

"Please, let me finish, Rory. When you followed me up to Kyle's bedroom, I wanted nothing more than to escape everything for a little while, and to pretend like everything was going to be okay. Part of me thought that if I could make you happy…physically…it would somehow make up for me failing in every other aspect of our relationship. When you didn't want me to go further – and you were right to stop me, Ror – I got angry because you were cutting me off from the one way I thought I might actually be capable of pleasing you. With that plan shot, I reverted to the one of making you realize how much I sucked, which resulted in me yelling at you. I followed you out of the room, but seeing you crying to Dean, and I know it was just a coincidence that he was standing there, but, it didn't matter; everything combined to just make me feel completely inadequate…So, I did the only thing I knew how to…I got mad. You know what happened after that."

Jess sat silently for a minute, his eyes swimming and his head filled with private thoughts. Rory reached out and gently brushed her hand on his arm. After a moment, he managed to turn to face her, despite the pain of seeing her face covered in tears he knew he had caused. He continued without breaking eye contact with Rory.

"My dad, Jimmy, showed up in Stars Hollow. He said he wanted to see me, though we only saw each other for a minute before he ran out the door – literally. That same night, I told Luke I wasn't going to graduate, and when I insisted that I wouldn't repeat 12th grade, he told me I couldn't stay there anymore. I was dumbfounded that he would stick to his guns on the agreement we had. Liz always was a pushover, but I should've known better with Luke. So, basically, I was feeling like a complete jackass loser, and I figured I might as well spare everyone the pain of dealing with me. Jimmy was good at leaving, so I figured I'd follow in his footsteps and leave, too. Besides, I couldn't stay with Luke, and I didn't want to stay with Liz, so I figured Jimmy owed me at least a place to crash in exchange for skipping out on me as a baby. Even if not, I felt I didn't have anything to lose. So, I headed out to California without saying goodbye. Saying goodbye meant I would have to explain myself, something I just wasn't prepared to do. So I lied, and told you I'd call you. Though I could tell by the look on your face you didn't believe me. I thought it was better that way. I felt that if you hated me, it somehow justified my treatment of you. I called you, always intending to say goodbye for real. But then, that one time, you said you may have loved me, but then said goodbye for me…and I realized I had screwed up, big time. I couldn't hate you for hating me, because you loved me. And then I had to deal with the fact that I had truly and utterly failed someone who actually loved me."

After another long pause, Jess finished with, "I know better now…about all of it. I'm sorry I put you through that. And those next two times I came back to see you were just the result of me trying to grow up and get my shit together, but not quite succeeding. I wasn't really ready yet. I'm sorry about those times, too."

Rory was feeling a bit overwhelmed by everything Jess had just revealed to her. She had no idea how to respond, but she decided a good start would be to reach over and take his hand in hers, so she did. Jess was a bit surprised she was still there and reaching out to him; she had every right to hate him. Instead, she shifted closer to him on the couch, turned, and leaned back against his chest.

They sat together in a comfortable silence for a good half an hour; sitting on the couch with his arms wrapped around her they both lost themselves in their own thoughts. Eventually, Rory decided she was ready to break the silence. She shifted her weight, and caught his eye.

"I understand now."

"Thank you for listening to me."

"Thank you for opening up to me."

"It was about time, Rory. It was about time."

She leaned back against him again and was soon yawning.

"Are you tired?"

"A little."

"Do you want to go to bed? You've had a long day…"

"No…I want to stay here with you a little longer…"

"Okay."

It was only a matter of minutes before Rory had drifted off to sleep. Jess checked his watch; 11:30, he should leave for the train station soon. Jess stood up carefully, trying not to wake Rory. She stirred a bit, but didn't wake. He went to her room and made sure her bed was made and then returned to the living room to carry her back. As he tucked her under her covers, he couldn't help but lean down to kiss her forehead. She smiled slightly in her sleep, and snuggled further under the covers. He made sure her alarm was set for the morning so she wouldn't miss her classes, and then returned to the living room and cleaned up the mess from their movie night. By the time he left, the only trace of his having been there at all was a small red Valentine, left on top of her clock.

AN: This is it for now. Don't worry, more is on its way, but it's time I slept a bit and did something away from the computer for at least a little while.

Please review! It inspires me to write, and then you get chapters faster. : )