A/N: Okay, time for a Literati first official date! If you like what you read, please send a review and let me know. Thanks, reader-peops! :)

(For disclaimer, etc. - see chapter 1)

Chapter 6

"Wow, look at you, Cary Grant."

"Hardly." Jess rolled his eyes as he passed by his uncle. "You have to wear a tie in these places or they don't let you in, okay?"

"You really booked a restaurant that fancy?" Luke asked, shaking his head. "I didn't know you even had the money for that."

"I saved," Jess told him shortly, trying to concentrate on fixing his hair in the mirror. "I'm sorry, weren't you the one who gave me the speech about treating Rory like a princess, the moment you heard we were together?"

"Pretty sure the word princess never came out of my mouth," said Luke firmly, his reflection appearing next to Jess' own in the glass. "But yes, I did say you should treat her right. Rory is a good girl, a little crazy like her mother, yes, but with a heart of gold. I will not stand by and watch her get hurt, not by anybody, and that includes you."

"Hey, I would not hurt her," Jess snapped, perhaps a little angrier than he needed to be at the slight implication that he could. "Not on purpose anyway," he muttered afterwards, realising all over again that he really had no idea what he was doing when it came to this whole dating thing.

If Luke started questioning him, he would have to try not to lose his cool, but the last thing he wanted to do was admit he was completely out of his comfort zone. Somehow, he seemed to have cultivated a reputation as a ladies' man, in spite of the fact he hadn't dated at all since arriving in Stars Hollow. Jess supposed it was that whole out of towner, troublemaker stereotype that had people thinking he was James Dean.

"Come on, Jess. I didn't mean..." Luke trailed off, looking awkward when his nephew looked his way. "I'm sorry, okay? I know you really like Rory, and I know it had to be rough, all that time she was with Dean and everything, but hey, at least in the end, she chose you."

"God knows why," Jess muttered, making a big deal of looking for his watch, because it was easier than paying any real attention to Luke.

"She knows, that's all that matters," his uncle insisted, "and I know that you're not going to screw up because... well, I just know."

At that, Jess dared a glance at Luke and found him smiling like he might actually mean it. Even months into his stay in Stars Hollow, spending so much time around both Rory and his uncle, Jess still wasn't used to people having faith in him. It was a foreign concept to a kid haphazardly raised by Liz, accompanied by a string of men too various to mention. Most of the time, he was lucky if anybody even paid attention to him, and when they did, they rarely seemed to like what they saw or heard.

"Thanks," he muttered, in response to Luke's remarks. "I should be going. Don't wanna be late," he added, fastening the strap on his watch and picking up his jacket to go.

"Wait a second," Luke called after him, his hand reaching out to Jess the moment he turned to look. "Here. I know you said you saved up and everything, and that's great, but I know how much I pay you and I know what fancy restaurant dinners cost. Take it," he insisted, proffering the money some more. "Seriously, I want you to. Call it a bonus if it makes you feel better. You do a good job in the diner and I don't think I tell you that enough."

"Thanks," Jess said again, nodding once as he took the money and stuffed it in his pocket. "I won't be late," he added, thinking he may as well.

He wasn't always great about taking his own curfew seriously, but he figured Rory would want to stick to hers. Heading out and down the stairs, Jess pulled the money Luke just gave him back out of his pocket and inspected it. The amount he found made him smile. Maybe his uncle was an even more stand-up guy than he gave him credit for.

Rory really wasn't sure why she was so nervous about a date with Jess. Not that her mom had helped at all, making the big deal that she had. Of course, it was nice to have her being positive about Rory's new relationship. It was plain as day that Lorelai preferred her little girl dating good old steady Dean Forester rather than Jess, who was more often heard referred to as the town hoodlum than anything else, but she was trying. Rory really appreciated that.

It had been kind of a surprise when Jess insisted he was taking her to dinner 'some place nice.' Rory had assumed that dating a guy like him would involve more just hanging out, or making out, or both. She would have been fine with that, for the most part, but she also liked the idea of a special first date.

When Jess knocked on the door, she actually had butterflies in her stomach and practically ran to let him in. It was strange to see him in any way dressed up, but Rory had to admit she kind of liked it.

"Wow," he said as he took in the sight of her. "You look great."

"Thanks." She felt her cheeks heat up at the compliment. "It's my mom's dress. I couldn't find anything that would work for a really nice place. Oh, and you look great too," she added, sure it sounded like an after-thought, even though it wasn't.

She was just so stupidly nervous, even as they walked to the restaurant together, his hand slipping around her own, which she didn't mind at all. They usually talked about all kinds of things, but suddenly Rory's head was empty of just about every topic and Jess seemed to be similarly afflicted, at least, at first.

"So, on a scale of one to ten, how weird do you feel right now?"

Her head whipped around to look at him and she found him smirking. It was almost as if he had read her mind, which was oddly comforting.

"I wouldn't say weird exactly," she told him, trying not to squirm. "It's just, well, this is different. You and me, on a real date."

"It is different," Jess agreed, nodding his head, "but the whole dinner thing was a good idea, right? I mean, I just thought you would want something special, so..."

"Special is great, I love special," Rory assured him. "Not that you had to, I mean, I wasn't expecting it, but it is really nice that you did, I just... Oh."

They had finally stopped walking and Rory was faced with the restaurant where Jess had clearly booked them a table. She looked from the door to him and back again at least twice, unsure how to vocalise the mess of thoughts in her head.

"What?" he asked, frowning some.

"Um, this place, Antonios, I've been here before," she said, clearing her throat before she could go on. "I, uh... It was a special occasion, an anniversary, actually, for me and..."

"Dean," Jess said for her, a light almost visibly dawning in his mind. "Great. That's just great."

"What can I get you?"

"Just gimme a cup o' Joe and a smile, sweetheart," said Lorelai, putting on her best Bogart voice, smirking hard when Luke finally looked up from his order pad and saw it was her. "Hey."

"Hey, yourself." He rolled his eyes at her antics but was smiling all the same as he got her the coffee she always wanted. "You're not usually in here so late on a Saturday."

"My daughter isn't usually out on a first date with the... the guy who mops your floor," she said swiftly.

She had changed her phrasing very definitely at the last minute from 'town hoodlum,' and hoped rather than believed that he didn't notice. Of course, he did.

"You know, I get it. Believe me, I know better than anyone that Jess is far from perfect, but lately, he's really trying, and not just with school either. I'm sure you noticed that he's been pretty serious about Rory for a while now..."

"Oh, I noticed. It'd be hard not to," Lorelai noted with a look, "and in the beginning, I'll admit, I did not like it. I mean, you were the one that told me what a troubled kid Jess was, and then with the attitude and the pranks and all. You cannot blame me for not exactly loving the idea of him trying to date my kid. And even if I had approved, she had a boyfriend already."

"I know that, and like I said, I get it, I really do," Luke insisted. "You know I care more about Rory than I do myself. If I thought Jess was going to do anything to harm or upset her, then I would never-"

"Hey, I know," said Lorelai, her hand over his on the counter before she fully processed what she was doing - the moment she realised, she retracted again fast. "Uh, in fact, what I was going to say was that things have changed lately, and not just with Jess either. Rory is getting older, more experienced with the whole dating thing. I never really expected her to stay with Dean forever, and her attraction to Jess is just about as obvious as his to her. What I'm saying is, if they want to do this whole dating thing, you won't hear me complaining about it," she insisted. "It's just... well, no matter who Rory dates, I can't help worrying just a little. It's what moms do." She shrugged her shoulders helplessly.

"Not just moms," Luke told her with a look that made her smile.

Sure, he could just be talking about being a worried uncle when it came to Jess, but Lorelai knew better than that. After all, hadn't he just said that Rory's life mattered more to him than his own? That was some real dedication. The only other person that she knew be so dedicated to Rory's welfare had been Max, and at least Lorelai was engaged to him. Even so, she was pretty sure Luke cared more, probably mostly because he had known them longer.

"You sure you're okay?" he asked then, jolting Lorelai from a strange daze. "You look a little... weird."

"Well, thank you, kind sir. I'm officially flattered," she said, giving him a look.

"I didn't mean... You know what I mean," he said pointedly.

Lorelai rolled her eyes. "Yes, I know what you mean. I don't know, maybe it's not all about Rory and Jess, The Early Years. Maybe I'm stressing a little about graduation too."

"Graduation?" Luke echoed. "Who's graduating?"

"Uh, that would be me," Lorelai explained with a smile. "I mean, it's not such a big deal really."

"Are you kidding me, it's a huge deal," said Luke, shaking his head. "You put in so much effort for your business classes, really knuckled down to some serious work, and I know that has not been easy, working a full-time job and raising Rory. You're amazing, Lorelai, and you should give yourself more credit."

The way he said it, the way he looked at her too, it all resulted in Lorelai feeling more overwhelmed than she ever could have expected to feel in a conversation with Luke Danes.

"Thank you, Luke," she said then, sure she was blushing horribly, but trying not to care. "You know, if I thought for a second you were as into this thing as all that, I'd invite you to come along to the ceremony, but you have a diner to run, so..."

"Give me a time and place, I will be there," he insisted. "Even if I have to close this place, I don't care. This is important to you and I wanna be there."

Okay, so maybe she could feel even more overwhelmed than before. Not that Lorelai was complaining, it was kind of nice actually. She was just struggling to understand how she suddenly felt as if she was the one on a date with a guy from the diner tonight, instead of Rory.

"This is nice."

Jess looked sideways at Rory, one eyebrow raised. "Seriously? We're eating sandwiches on a bridge in the dark," he told her, shaking his head. "You think this is a nice way to spend a first date?"

"Hey, they're really good sandwiches, this bridge happens to be one of my favourite places in town, also the spot where we finally decided to be together and shared our first kiss, and it is not dark, it's just... romantic," she insisted, going so far as to poke out her tongue at him for good measure.

"You're cracked," he told her, but was smiling all the same, unable to help himself.

Trust Rory to always find the good in every crappy situation. Not that Jess supposed it was all that bad really. She had a good point about the food - Al had really outdone himself with the knock-off Subway-style sandwiches - and the bridge really was a significant place for himself and Rory. He supposed eating by moonlight did have its romantic side too, it was just that, between the wooden surface he was sitting on and the chilly breeze, he was starting to lose some feeling in a few places.

"If I'm cracked and you're the guy who wants to date me, what does that say about you?" asked Rory smartly, popping the last bite of her sandwich into her mouth.

"I don't know." Jess shrugged, wrapping up the rest of his own food and putting it to one side a while. "Either that I'm crazier than you are or..."

"Or?" Rory prompted when he trailed off to nothing.

Jess swallowed hard, not entirely sure what the rest of that sentence was even supposed to be, or maybe he knew exactly and he was just too afraid to admit it, even to himself. Jess Mariano had never been in love. For a long time, he wasn't even sure he knew what that meant and was damn sure that if it did exist outside of books and movies, it was never going to come his way. Then came the day when he first came face-to-face with Rory Gilmore. He had liked girls before, been attracted, dated, had sex, everything, but nothing, absolutely nothing, could have prepared him for what he felt the moment their eyes met that first day.

"Jess, are you okay?" she asked, suddenly frowning with worry.

He really hadn't meant to cause that and hated himself immediately for doing so. Not that he thought he was actually capable of screwing up this first date at all. They already had to abandon the idea of a romantic meal in a fancy restaurant because he had managed to pick the one place in town that Rory had spent a special anniversary with Forester, and even then, they had made the best of the night. Rory had been smiling almost constantly, at least until the last minute or so.

"I'm sorry," he said then, wondering when his own voice got so soft. "You know, that tonight wasn't exactly what we planned. I'm not this guy, Rory. I've never... The whole serious dating thing, it's not really me. I mean, I'm trying, but I think you're going to have to cut me a little slack sometimes, you know?"

"Jess, I'm not expecting you to be the perfect boyfriend," Rory told him easily. "I can't be the perfect girlfriend either. All we have to do is our best, because I think there's a good chance that we could be perfect for each other, right?"

That made him smile. "Right," he agreed, nodding slightly as he leaned in closer, capturing her mouth with his own.

Maybe it was a romantic, almost-perfect first date after all.

To Be Continued...