The whole title for this chapter is: First Days, Country Club Golfing, and Missed Opportunities

Hugs to my beta BrokenDaisy. Thanks for all the help :)

This chapter starts during The Lorelai's First Day at Chilton and stops right before The Deer Hunters. I was going to go up to Cinnamon's Wake, but I couldn't figure out what I wanted to do with the deer episode. I may end up skipping it. We'll see.

Anyway, I really hope you enjoy this, there are a few lines from the episodes (I do not own those or these characters), and I thank everyone who reviewed, alerted, or favorited last chapter.

So, thanks for reading, drop a comment if you can, and I should go.

See ya!

GG

1999…

Jess was sitting on the gazebo steps, reading a book, when a shadow fell over him. He looked up, the person's face in the shadows. He could tell she was female, and he didn't realize he was staring at her chest until a familiar voice said, "I've been told my eyes are my best feature, and those are not my eyes Mister."

Jess face burned red as Lorelai's smiling face swam into focus. He stammered an apology, pushing himself to his feet.

"Hey, don't worry about it. If I had a dollar for every time a guy leered at me…" Lorelai trailed off, a faux shudder running down her spine. "At least you have the decency to apologize." Jess looked down at his feet, still ashamed of what he had done. This was his best friend's mother. She was like his mother sometimes, too. He couldn't be…

"How's about we pretend this never happened?" Lorelai suggested after a heavy pause. "How does that sound?"

"Thank you," Jess muttered clutching his book tightly to his stomach. "I-I'm really sorry," he whispered after another beat.

"For what?"

"For…" he noticed the wink Lorelai gave him and nodded. It never happened. He could easily live with that.

GG

Present Day…

Jess was just collecting his backpack when the door opened. He looked up, his eyes widening at the sight. Lorelai's outfit left nothing to the imagination. She looked like a better looking Daisy Duke, and it took all of his self-control to look away.

"I-I have to…" he rushed out of the diner, barely hearing Luke say good-bye. As he walked to school, Jess thought about the day on the gazebo. He had never told anyone about that day, not even Luke or Rory. It was still between Lorelai and himself, and he was going to keep it that way for as long as...

"Oof!" The breath was knocked out of him as he ran into something solid. The impact knocked him out of his thoughts, and steady hands caught him before he hit the ground.

"I'm sorry," a familiar voice apologized and Jess looked up to meet Bootsy's eyes. "You okay, kid?"

"I'm fine. Sorry," Jess replied glancing back at the diner. Bootsy followed the younger guy's gaze, letting out a low whistle.

"No wonder you're distracted. I'd be too." The older man shook his head slowly. "I never would have guessed that she had a kid."

"Uh…" Jess' face was burning. He didn't want to have this discussion about Lorelai; especially with Bootsy. "I need to…"

"Yeah, school," Bootsy mumbled distractedly, still staring at Lorelai.

"Bye." Jess jogged towards campus, making it just as the first bell rang.

GG

As the day progressed, and he got over the surprise of seeing Lorelai dressed so stripper-y, did Jess realize that this was Rory's first day at Chilton. At random moments, he wondered what she was doing and who she was getting acquainted with. He wondered if rich kids were just as bad as they were depicted on crappy television shows or if they were actually okay. He also wanted to know if he was going to miss her every, single day she was gone.

"So, Rory wanted me to tell you that if she doesn't survive you are welcome to her CD collection," Lane said the moment Jess sat down at their lunch table.

"That doesn't sound like Rory," Jess replied softly.

"Okay, so I asked if I could have it, but she agreed. And I thought you'd want to steal her David Bowie stuff."

"But I thought you wanted Bowie."

"I do, but it's only fair you get him. I've had my eye on the Distillers for a while and I know you want them."

"At least you have your priorities straight," Jess joked and she threw him a small smile.

"I miss her," Lane admitted quietly, after a lengthy pause.

"Yeah," Jess replied just as quiet, "me too."

"Whatcha talking about?" Dean asked as he sat down at their table, breaking up their little moment.

"Music," Lane responded fixing her glasses. "Do you listen to any music?"

"Some," Dean said, opening his milk carton.

"Such as?" Jess prompted actually a little curious to the taller boy's music preferences.

"I actually like hip-hop. You know the older stuff: MC Hammer, Run DMC, Digital Underground," Dean replied shrugging. He brought his milk to his lips but lowered it at the looks they threw him. "What?"

"You just don't seem like the type to listen to stuff like that," Lane stated picking her fork up.

"And what do I look like I listen to?"

Lane and Jess shared a quick look before simultaneously saying, "Vanilla Ice." They laughed at the appalled look on Dean's face.

"And what do you two listen to?" Dean asked curiously once their laughter subsided.

"It really depends on where I am at the time," Lane informed the taller boy. "Sometimes it's old, Christian hymns; while other times it's The Rolling Stones or Yoko Ono."

"Yoko Ono?" Jess gave Lane an incredulous look. "She's the reason The Beatles broke up."

"They were going to break up anyway. It's just like a guy to blame the woman instead of admitting the band had problems," Lane defended her favorite singer.

They launched into an argument that lasted the rest of lunch and amused Dean to no end. By the time the bell rang, Jess and Lane agreed to call it a draw for now. The three walked out of the cafeteria, Lane heading to band while Jess moved down the hall to his locker.

"Do you two argue like that a lot?" Dean asked leaning against the locker next to Jess'.

"Not much," Jess replied shrugging nonchalantly. He and Lane never agreed on bands just like he and Rory never agreed on books. It's what made their friendship fun; the fact that they could argue good naturedly without really getting anywhere.

"So, I'm starting at Doose's tonight. Any advice?"

"Keep Taylor happy," Jess suggested closing his locker door.

"And how do I do that?"

"Shelf the peaches correctly?"

"I thank you for your help," Dean stated with a touch of sarcasm in his voice. The bell rang. "That's my cue to leave. I'll see you in Chemistry."

"Okay," Jess replied heading towards the gym. Once he got past constantly talking about Rory, Jess had to admit Dean wasn't that bad. They still weren't quite friends, but he also didn't want the guy to leave him alone. There was a possibility they could be friends; maybe; in a few years at least.

Or at least by graduation day, Jess thought just as the bell rang. It had to be better than nothing.

GG

The bell rang over the door, catching Luke's attention. He was surprised to see Lorelai step into the diner, this time dressed more sensibly. She normally didn't stop by at this time of day, but it sure beat talking to Kirk.

"What are you doing here?" he asked curiously walking past her towards the counter.

"See, now, that's why you were voted Mr. Personality of the New Millennium. Where's your crown?" Lorelai retorted sarcastically moving towards a stool. She removed her bag and sat down.

"I just mean, you don't usually come in this time," Luke explained fighting an eye roll.

"Well, I have to pick up Rory from school," Lorelai replied. Luke placed a mug in front of her and grabbed the coffee pot. She thanked him when he poured her some coffee.

"You're welcome," he said replacing the pot.

"No lectures?" she asked curiously.

"My blood sugar's low. I'll eat an apple and get back to you," he snarked back, writing something on his order pad.

"God," she sighed taking a sip, "this has been one hectic, bizarro day for me."

"Yeah?" Luke questioned

"Yeah, this morning with the being late and my mother existing." She rolled her eyes. "Oh, and this father," she started getting Luke's attention, "this father from Chilton, he, uh, drove out to the inn all the way from Hartford to ask me out."

"Really?" Luke kept his eyes locked on his notepad, hoping he looked nonchalant. "You going?" he asked with more curiosity than he was aiming for. So what if she was asked out by some Chilton dad. What did he care?

"No. He's got a kid in school with Rory, and the whole thing just seemed a little weird."

"Oh good," he said finally looking up from his order pad.

"Good?"

"Yeah, I uh, think it's good that you turned him down," Luke replied turning back to the counter, hoping to hide the look of relief on his face. Again he wondered why he cared so much.

"Okay," Lorelai replied slowly. Luke could tell she wanted him to explain.

"I mean, he's probably old, right?" he said turning to look at her.

"Old?"

Luke knew he was in hot water, so he chose his next words carefully. "Yeah, I mean, he's got a kid in high school."

"Luke, we've got kids in high school," she pointed out, a smile on her face.

"Yeah, but you had Rory when you were young, and I wasn't exactly an old geezer when I got Jess. Most people aren't that young. Most people are, uh…"

"Old," Lorelai supplied still smiling.

"Yeah."

"Like this guy who asked me out."

"But you're not going," Luke said quickly.

"No, I'm not going."

Luke nodded, looking back down at his order pad just as Lorelai's cell phone rang. "Oh, that's me," she announced and Luke promptly pointed at the sign on his wall before heading into the kitchen.

After a quick conversation with Babette she hung up and said. "Um, I have to go." She removed her wallet from her purse.

"Keep it. I gave you decaf."

She frowned slightly, but still stood up and walked towards the door. Jess was walking in just as she was leaving and she greeted him with a smile. "Hey Jess."

"L-Lorelai," the kid replied, his face turning bright red. "Nice to… seeing you, L-Lorelai." She smiled, shaking her head, and let the door close behind her.

"What the hell was that?" Luke asked as his nephew took a seat on the stool Lorelai occupied not even a minute ago.

"What are you…? I don't…" the kid was clearly flustered. "Do you need any help?"

Luke eyed his nephew cautiously, but still handed over the order book. "Take orders while I work the grill, Romeo."

"S-shut up," Jess stammered, his face reddening two shades darker. He stood up, nearly knocked over the stool, and moved towards a table.

GG

Jess was taking the garbage out that night when he spotted Lane, Lorelai, and Rory walking down the sidewalk. He couldn't hear what they were saying, but he figured it had something to do with Lane's mother; especially when the bespectacled girl took off with pizza crust in her hand.

After she was gone, the Gilmore girls continued down the sidewalk, talking about something Jess still couldn't make out. It wasn't until they stopped within hearing distance of him, did he realize it was about some girl named Paris. He almost stepped out to greet them, but stopped when Lorelai said, "Hey, what do you think of Luke?"

Eyebrows furrowed, Jess stuck to the shadows and waited for Rory's answer. "What do you mean?"

"I mean, do you think he's cute?" Jess very, nearly snorted at Lorelai's response. Was this Lorelai's way of saying she liked Luke? Jess had never really thought about the two as a couple before, but it could work. They were a better couple than the few women Luke had dated over the years. He didn't even want to think about Anna, and Rachel had been cool until she up and left one day.

"Oh, no. No way." Rory's words had Jess' eyebrows shooting up in surprise. Did she not think her mother and Luke would be good together? They already spent a big chunk of time around each other. What was so wrong with them dating?

"No way what?"

"You cannot date Luke." What was so wrong about dating Luke? Jess thought.

"I said nothing about dating Luke," Lorelai quickly defended herself.

"If you date," Rory plowed on, acting as though she hadn't heard Lorelai. "You'll break up, and we'll never be able to eat there again."

"I repeat, I said nothing about dating Luke."

"Date Al from Pancake World, his food stinks." Still, Rory wasn't listening to her mother, but Jess was listening intently to Rory.

"I cannot believe what I'm hearing." Jess actually thought Lorelai was going to defend the idea of dating Luke, buy instead she made a joke, "Al's food does not stink; Al stinks."

As they walked away bickering, Jess couldn't help wondering if that's what Rory thought about them dating. Would she feel obligated to avoid the diner if they broke up? And was she acting a bit too hasty on the actual breaking up? Who's to say they weren't going to be together forever? Why, in her eyes, did they have to break up?

"Jess, are you still taking the garbage out?" Luke called from the diner's front door.

"Uh, no," he replied moving out of the shadows of the alleyway. "I'm coming.

GG

1996…

Luke heard grumbling through the open window as he walked up Lorelai's porch's steps. He furrowed his eyebrows as he stopped in front of the door. He very nearly walked away when he heard something fall over and a sharp swear word, but thought better of it and knocked.

"Unless you are the anvil here to fall on my head, I'm not home," Lorelai called as she approached the door. She pulled it open, looking up at Luke's face. "Oh, it's you. I thought you were my mother coming to destroy my hopes and dreams."

"Your mother has your new address?" Luke asked curiously as Lorelai let him into her house.

"No, but I wouldn't put it past her to interrogate every, single person in this town until she found it," she replied closing the door.

"So, I take it you're in another fight with your mother," Luke guessed stepping into Lorelai's messy living room. She had been living in, what she affectionately called, The Crap Shack for a little over two months and had yet to unpack every box.

"Not exactly," Lorelai admitted clearing a spot on an old chair so Luke could sit down. "She called the inn yesterday, insisting that I let her take Rory to the country club her and dad belong to. They want to show her off like some show dog."

"And I'm guessing you told her no."

"You're damn right I told her no. I'm not letting them parade my kid around to some rich, fat, gawky guys in weird clothes who do nothing but play golf all day. Do you know what rich, fat, gawky guys do to little girls?"

"I doubt they're all rich, fat, and gawky like you describe." She threw him a sharp look. "Not that they aren't all normal either. I'm sure there's one guy who just stands around, staring at people." He really wished she'd change the subject.

"I know I'm being unreasonable," she pointed out softly, after she calmed down, "but my mother needs to understand. I don't want Rory growing up around all that. It drove me absolutely crazy by the time I was ten, I don't want her to feel the same way."

"I know," Luke replied gently. "So, what'd you need me to do today?"

She smiled and stood, walking into the kitchen. She returned a few seconds later carrying a list. "It's just a few small repairs around the house; nothing big."

Luke took the list from her, glancing over what she needed done, and got to his feet. "I'll get my tool box."

As he headed towards the door, he heard her say, "Thanks."

"No problem," he responded knowing she wasn't just thanking him for the household repairs. He'd always be there for her, no matter what she needed.

GG

Present Day…

"Is fishing an option?" Lorelai asked as she and Rory sat at a table by the window. "Because I bet Luke would definitely take you if it was."

"Mom, the options are right here," Rory said handing the list over, "and I do not see fishing anywhere on that list."

"Hey Luke!" Lorelai called ignoring Rory. "Is fishing a sport?"

"What?" the diner owner called back, still trying to figure out why the two most uncoordinated women on the planet were talking about sports.

"Is fishing a sport?"

"To some people," Luke replied balancing two plates as he carried the girls' dinner to them. "I guess it really depends on what you catch."

"For Luke it's a hobby," Jess pointed out from the counter, going over his math homework. "He barely catches anything bigger than minnows."

Luke glared at the back of his nephews head. "And for Jess it's a pain."

"It'd be less of a pain if you'd just let me read on the dock," Jess said turning to face Luke.

"We don't go fishing so you can read."

"Yeah, fishing is a sacred bonding moment between men," Lorelai supplied in a deep, mocking voice, "where one man proves he is superior to another by catching the biggest fish, or, in most guys' cases, drinking the most beer and belching loudly."

"You watch too much TV, Mom," Rory pointed out glancing down at her list of sports.

"Why are you taking a sport anyway?" Jess asked curiously, returning to his math homework. "Last I checked you are terrible at sports."

"It's required at Chilton," Rory responded and Luke caught sight of her crossing off volleyball and basketball. "Maybe I should just join the swim team."

"Honey, you tried to swim remember?" Lorelai said munching on a French fry. "The nice instructor lady had to practically pry you off the wall with a crowbar."

"Yeah," Rory muttered as she crossed off swimming. "What about field hockey?" She made a face, answering her own questions. "Never mind." She crossed it off, too.

"What's left?" Lorelai asked, glancing at the list.

"Horseback riding and golf."

"Oh, if you ride horses I can get you a pair of cute cowgirl boots and a ten, gallon hat. Both, naturally, would be pink and sparkly."

"That's not the kind of horseback riding they are referring to," Rory pointed out as she promptly crossed it off. "And I don't think I want to ride a horse anyway."

"Yeah, you did freak out when I placed you on that pony."

"I was six."

"You still freaked out."

"Golf?" Rory said returning to the subject at hand.

"Golf it is," Lorelai replied returning to her dinner. "Though, who do we know who plays golf on a regular basis?"

"Well there's…"

"Oh look, an L-shaped French fry," Lorelai exclaimed picking it up. "Who let this get passed them at the fry making plant? Don't they, you know, shun the oddly shaped fries? It's like getting a burnt or green chip in the potato chip bag. I must alert the fry police."

Rory shook her head, but folded her sports list up and placed it in her pocket. As she returned to her food, Luke thought over what had just happened. He knew Rory was about to suggest her grandfather. He also knew Lorelai was going to put her foot down. He recalled what Lorelai said, at her house, all those years ago, about Rory going to that country club. He wondered how far Lorelai would go to keep Rory away from that place, and what Emily Gilmore would do to insure that her daughter failed. He was not looking forward to the fallout.

GG

It was a few days after the sports thing when Lorelai walked in, in a bad mood. She slammed her bag on the counter, sat down heavily, and laid her head down. Luke placed a cup of coffee next to her and said, "Is there a problem?"

"Are my boobs bigger than Rory's?" she asked suddenly, taking Luke by surprise.

"What?"

"What?" She looked up, shaking her head. "Nothing, sorry."

"What's going on?"

"Nothing. This wedding is stressing me out and Rory and I had this stupid fight. Don't worry about it."

"Is this about her golfing with your dad?"

Lorelai was quiet for a few seconds, but eventually blurted out, "I can't believe she had fun. I never had fun at the club. Why would she…?"

"Maybe you two aren't as similar as you thought," Luke muttered as he began refilling sugar dispensers.

"Take it back," Lorelai exclaimed in a mock hurt voice. She shook her head, running a hand through her hair. "I guess I never thought she'd actually enjoy that life. I mean, I want her to get to know my parents-it's not fair to her to not have a relationship with them just because I don't-but…"

"You don't want her to get too close and leave you behind," Luke said softly.

"Have you and Sookie been talking behind my back?" Lorelai asked curiously.

"I'm just saying…"

"Yeah, I know. I'm being stupid."

"No, you're just…"

"Jealous," Lorelai supplied, nodding her head. "I'm a child who is sad because no one will play with her. I need a time out." She picked up her coffee cup, taking a sip. "Thanks, you know, for listening to me."

"Anytime," Luke replied moving towards the kitchen.

"This isn't decaf is it?" Lorelai asked sniffing the contents. "That was a cruel trick the other day."

"I thought it'd make you less crazy. Did it work?"

"What do you think?" she retorted draining the remainder of her beverage. She tossed some ones on the counter. "I should go and apologize." She started towards the door. "See you, Luke," she called over her shoulder, letting the door close behind her. He had a feeling her parents were going to become more of a problem for Lorelai as the years went on, but at least he was able to semi-help her with this hurdle.

GG

"Who needs this much crap for school?" Jess asked as he looked over the list of school supplies Rory had neatly written out.

"Chilton is very demanding," Rory replied grabbing the last slice of pizza from the box.

"I'm surprised it hasn't asked you for your soul," Jess muttered replacing the list on the Gilmore's coffee table.

"The place isn't that bad," Rory insisted munching on her pizza. "I mean, the classes are a tad more demanding and the kids aren't Star's Hallow kids, but things aren't all that bad. Mr. Medina is really nice and I actually got my locker open yesterday."

"Hey, at least there's a bright side." Jess fiddled with the watch on his wrist, looking anywhere but at Rory. "Hey, Rory."

"Yeah?"

"So, they were out of root beer, but I got some orange soda instead," Lorelai's voice said as she opened the door, cutting off what Jess was about to say. "Did I miss anything important, and who the hell ate all the pizza?"

"I told you we should have gotten two," Rory pointed out, getting to her feet. She took one of the shopping bags from her mother and glanced inside. "You got Red Vines and Twizzlers? I thought you boycotted Twizzlers when they started making the chocolate ones."

"I figured it's not the strawberry Twizzlers fault that the company made that disastrous candy," Lorelai replied setting the other bag down so she could take her jacket off.

"And you missed them," Rory supplied as she sat back down next to Jess.

"I admit nothing," Lorelai exclaimed taking a seat on the floor. "So, really, what did I miss? Since Mr. Anti-Pause Button wouldn't stop the film."

"It could ruin the tape," Jess defended his decision.

"Just as bad as Luke," Lorelai muttered shaking her head. "What has that man done to you, my dear boy? Live with us for a few days, and we'll bring you to the dark side."

"We even have ice cream," Rory prompted waving a gallon of mint chocolate chip under Jess' nose.

"I think I'll pass," Jess replied smiling. "Besides, I think two Gilmores are all this town can handle."

"What are you talking about? One more would do more good than harm," Lorelai said quickly. "We'd be the Gilmore trio: me, the dashing leader, Rory, the meek sidekick, and you, Mr. Anti-Pause Button."

"Oh, look, Kate Hudson took some pills," Jess said pointing at the screen. "I hope she doesn't die."

"You've seen this movie eight times," Rory pointed out, an amused expression on her face.

"And this scene gets me every time," Jess snarked back, throwing her a small smile.

When the movie wrapped up, Jess said good-bye to the eccentric Gilmores and headed home. He wondered what he would have said to Rory had Lorelai not shown up. There was so many ways that conversation could have gone, and a part of Jess was glad Lorelai showed up when she did. He avoided sticking his foot in his mouth and making a fool out of himself.

But, he still wondered, what if she hadn't shown up. Would they have talked about what he overheard a week ago? About how Rory firmly believed that if Luke and Lorelai (or anyone else for that matter) dated, they'd have to avoid that diner? Or would they have talked about how Dean was always hanging around the bus stop, hoping to catch glimpses of Rory. Maybe they would have talked about Rory's feelings for Dean. Or maybe his feelings for…

No, it was good Lorelai showed up when she did; it would have been a disaster if she hadn't.