A/N: Big thanks for the reviews on the previous chapter - especially the one that had OMG in Janice-from-Friends style! lol - I know it was mean to have Jess get a black eye from Dean, but I just couldn't resist the irony :)

(For disclaimer, etc. - see chapter 1)

Chapter 9

"I don't know, it just felt so weird!"

"I'm sorry, how can a nice, decent looking, intelligent guy asking you out on a date feel weird?" asked Lorelai, feeling genuinely confused, and not just because she really was struggling to figure out why she couldn't find her favourite necklace anywhere! "I mean, he sounds nice, and he's at Yale, so smarts is a given. I admit, I threw in decent looking just because I can't imagine you being asked out by an unfortunate looking guy. Is he unfortunate looking? Is that the problem? Because you're such a good kid, I can't picture a world where you're that shallow. Even Mommy isn't that shallow!"

"I am not shallow, but no, Trevor is not at all lacking in the looks," Rory confirmed, as Lorelai carefully balanced the phone under her chin, so she could use both hands to double-check the necklace wasn't in amongst the magazines and papers on the coffee table. "There is seriously no good reason for my saying no when he asked me out, except... well, like I said, it felt weird. I don't know why it did exactly. Maybe there's something wrong with me."

"Babe, there's nothing wrong with you," Lorelai told her, like a reflex, sighing heavily - no necklace yet. "It's just, well, you haven't really dated much."

"Um, excuse me? I've dated plenty. I dated Dean. I dated Jess."

"Uh, no, honey, you had one boyfriend, and then, you had another boyfriend. Sure, you went out on dates with those boyfriends, but it's not the same as dating. You know, when a guy asks you out and you go, and then, some other guy asks and you go out with him? It's called playing the field, sweets, and I think maybe it's time you tried it out a little. Bingo!"

"I'm sorry, bingo?" Rory asked in confusion.

"I found it. The necklace I've been searching for, you know, for like an hour now! I didn't mention that?" Lorelai frowned on realising maybe that really hadn't come up in their conversation yet. "Huh, I really didn't. Anyway, your need is greater, babe."

"Which necklace?"

"Oh, the silver chain with the pink crystal thingies?"

"Ooh, pretty!"

"Yes, very pretty," Lorelai agreed, putting the necklace carefully into the pocket of her jeans. "But so not the point right now. You got asked out by a nice guy and you said no. Now, that's fine, you're totally allowed to do that, but since you called me all of a flutter about it, I'm thinking maybe you changed your mind already?"

"Kind of, maybe." Rory sighed. "I don't know, Mom. It's like you said, I guess I never really have dated, not in this way, and there's nothing to stop me from doing it now, the dating thing, I mean. Well, except for..."

"Except for?"

Lorelai almost thought she knew what was coming before Rory ever said it, to the point where she actually mouthed the next word right along with her daughter.

"Jess."

"Hmm, I was wondering about him. You guys have been talking a lot, huh?"

"Talking, texting, seeing each other when I come home," Rory admitted, sounding just a little sheepish about it. "I mean, that is all it is. We're just friends now and I know that's probably for the best... right?"

There was a part of Lorelai that so wanted to say, 'Yes, that is absolutely for the best,' and push Rory at this Trevor guy so hard. On the other hand, she knew how unfair that was, not just to Jess and Rory, but also to Trevor too. After all, they had established the kid was nice enough. It seemed pretty mean to give him false hope if Rory really was just going to end up back with Mariano again before the month was out.

"Sweets, you know I'm not going to actively tell you who to date and who not to date," she said, after a moment's thought. "I know I maybe did a little of that before, but I shouldn't have, and now, it would be a total no-no. You're nineteen, Rory, and out on your own at Yale. It is really not okay for me to be making these decisions for you any more, if it ever was."

The way her daughter sighed so heavily proved she would almost have rather been told what to do. That was Rory all over. She was good with instructions and structure in general. Not because she couldn't think for herself, because she absolutely could, she just worried so much about potentially screwing up, especially in ways that might hurt others. It wasn't a bad trait, but it did mean she got scared about change sometimes.

"I don't know, Mom," she admitted then. "Me and Jess, it's so complicated. We said we were just going to be friends, and that is working out for us, but sometimes... I guess I just keep on wondering how it would be if we tried to get back together, but then, I remember how badly that went last time. It's such a weird situation. The one advantage to Trevor would be no back story and no baggage, I guess."

"So, hey, maybe try one date with him and see how it goes. It's not exactly a commitment. You are under no obligation to ever go on a second date, and also, it's not as if Jess can be mad about it. Like you just said, you two are friends right now, nothing else."

"All true. I'll think it over some more. Thanks for the advice, Mom."

"Any time, babe." Lorelai smiled.

Necklace found. Daughter feeling better about her love life. Not a bad day's work so far, and it was only eight-thirty. Of course, realising the time put Lorelai back into motion pretty fast, just as soon as her call with Rory was done. She was meeting Natalie, the new designer for the inn, at the diner at nine. She was going to have to hustle!

"You know, if anybody else was taking up half your tables with their business arrangements, you would completely lose your mind about it."

Luke turned around to look at Jess, knowing the smirk would be on his lips long before he ever saw it.

"Lorelai isn't just anybody," he reminded his nephew, despite the fact he knew that well enough already. "Don't get me wrong, it's driving me a little crazy," he continued, in a lower voice, just in case she overheard, "but... it's Lorelai," he added, shrugging his shoulders.

"Yeah, I get it," said Jess, smirk slipping some as he moved away to go serve some other customers.

Luke sighed. Poor kid had it bad, he knew that. The whole situation with Jess and Rory when they were together was one gigantic mess, but now they were back to being friends, it might actually be worse. Luke knew what it was to be caught up in the friend zone of the woman you were in love with. He had spent enough time in that position with Lorelai. Seeing Jess go through the same thing with Rory had been tough enough the first time, but here on the second go around, with the poor guy knowing for sure what he was missing out on? It was no joke.

Unfortunately, there was little to nothing Luke could do to help. He certainly couldn't blame Rory for being wary after the way Jess treated her, and talking to Lorelai about the whole thing just put everybody on shaky ground. Though they were both on their best behaviour, things were unlikely to ever be super friendly between Lorelai and Jess. Again, understandable, but it really didn't make life any smoother.

"Hey, you."

Luke had gotten so lost in thought, he missed the part where Lorelai was suddenly right in front of him, leaning over the counter for a quick kiss.

"Hey," he greeted her right back. "Everything okay with your designer?"

"Meh, I guess so." Lorelai shrugged. "Do I love that she has previously worked with my mother? Um, no, I do not, but Natalie is so damn good at what she does, I think I'm just going to have to believe her when she says she hasn't seen or talked to Emily in forever, and would absolutely never, ever mention me and the working together if she did."

"Sounds like a workable plan." Luke nodded in agreement. "So, no problems?"

"Hmm, not right now," said Lorelai thoughtfully. "Just so long as Taylor doesn't try and pull any more crap with our paperwork. Seriously, what did he think he was doing? Threatening not to give us our permits if you didn't let him have his ice-cream truck outside the diner? After what he did to Rory with that whole ice-cream queen thing, he's lucky I didn't tell him exactly where he could park his truck," she said with particular emphasis that even the dumbest person couldn't fail to understand.

Luke tried not to smile too much. "Yeah, well, you do know I couldn't actually stop him parking out front anyway, right?"

"Yes, I know that, and you know that, but Taylor doesn't seem to know that, and I plan on keeping it that way," she said with a grin. "Besides, if he starts making either of our lives difficult any time soon, I vote we set Jess on him. Apparently, he's pretty good at scaring the pants off the guy."

"I wouldn't go that far," said Jess himself, having appeared at the cash register to ring up somebody's bill.

Luke looked from Lorelai to his nephew and back again. It really had scored Jess some serious points with her when he stood up for Rory the way he did. Not that that was why he did it, Luke was sure, and had told Lorelai as much. He just cared, that was all. Though it wasn't his place to be throwing around the L word on someone else's behalf, Luke was 99% sure that Jess' heart was entirely in this thing with Rory. It was why it was so tough to see him pining the way he was.

"So, you think she'll be around at all this weekend?" he asked Lorelai, loud enough that Jess would hear. "Rory, I mean."

"Oh, I don't know. I mean, maybe but, uh... she might have plans."

The look on her face suggested there was something else she could have said if Jess wasn't standing right there. Luke wasn't sure he liked that much. It either meant that Lorelai didn't want Jess to know Rory was coming home so he couldn't seek her out, or it meant she wasn't coming home for some reason Jess might not appreciate. Like another guy maybe. Luke winced at the very idea and scrambled for a subject change. Before he could, Lorelai came up with one on her own.

"I was actually thinking, since Rory most likely won't be around, maybe you would want to come over, say Saturday? I'm seriously jonesing for a movie night and without my girl, I thought maybe I could use you to sub in?"

"For Rory?" Luke checked.

Lorelai made a face. "Obviously not exactly. Come on, I know the difference between movie night with my daughter and movie night with my man. Several key differences," she said pointedly.

If Luke were the type to blush, he probably would have. Instead, he cleared his throat, tried to ensure that Jess could neither see his face nor hear his voice, and leaned in closer to make his arrangements with Lorelai.

"I could come over for movie night," he told her easily. "You have any particular movie in mind?"

"Luke, I always have a hundred movies in mind!" she reminded him with a grin. "But it should be something you'll like too, or something you haven't seen maybe?"

"Trust me, I haven't seen anything..."

If they were trying to keep their conversation private, then they were doing a lousy job. Jess wasn't mad about it, because he was pretty sure, at least in part, that Luke and Lorelai were trying to save him from himself. He didn't really need to hear why Rory was probably not coming home this weekend. Somehow, he just knew it wasn't a studying thing, because that would have been said loud and clear. That meant she had plans with somebody else, maybe something date-like.

Of course, the other option was that she was simply avoiding him. Things had gotten a little awkward last Sunday in the apartment, by way of an almost-kiss that he had been thinking about more than a little ever since. He had probably blown it. It wouldn't be the first time, Jess realised with a sigh. He and Rory were most likely less back to square one and more six miles further back than that.

"Or twenty-two-point-eight miles," he muttered himself, going to bus some tables.

After all, he didn't need to hear any more of Luke and Lorelai with their cutesy movie night chatter. He absolutely believed his uncle when he said he hadn't seen anything, even if Lorelai did looked amazed.

From what he heard as he passed by them then, Casablanca seemed to have been chosen as the classic for tonight's viewing. Jess smirked at the very idea of his uncle enjoying a movie like that. Not that they were necessarily going to see much of the movie. That thought wiped the smile off Jess' face very fast. Happy as he was for his uncle, he really never, ever needed to be thinking of Luke that way with anybody, ever!

To Be Continued...