Quick A/N: Thanks to Maya for beta-ing and helping when I got stuck. So...if there are any mistakes...blame her. :D

Chapter 9- Dining Emily and Richard

Friday night dinner at the Gilmore household was going as usual; a bit of fighting, a generous amount of reprimanding, and a bucket-load of headaches. That was, until Emily Gilmore spoke up.

"Those kinds of things are always obvious. You know, when a couple is in a relationship and then suddenly isn't."

Lorelai set her fork down, ready for whatever was coming.

"Yeah, I guess," Rory said warily.

Emily gave Rory a pointed look. Rory turned to her Mom. "Is she still looking?" she whispered.

Lorelai sighed. "Yup."

"Right. Um, you know, Grandma, did I mention that unfortunately I'm not with Dean anymore?"

Emily set her silverware down as well. "No, you didn't."

"Well, I'm not," Rory confirmed.

Richard spoke up. "Well I think that this is good news. He wasn't right for you…and it's good to be single while you're so young."

Lorelai shot her dad a glare.

Emily interrupted. "Well, yes, I've known for weeks actually."

"Oh? How?"

"Well, you very abruptly stopped mentioning him twelve dinners ago, so I figured that was the case," explained Emily.

Rory swallowed the piece of potato that she had just put in her mouth. "Well, I'm sorry I didn't tell you Grandma, Grandpa."

"Well, I think you should have. I mean, what if I had invited Dean to an event and you were no longer with him, and that's how I found out? It would've been embarrassing."

Lorelai snickered. "What sort of event would you have invited Dean to?"

"I don't know…a wedding?" Emily pursed her lips.

"For who?" Lorelai shot her a skeptical look.

Emily rolled her eyes. "A mutual friend or something."

"You and Dean have mutual friends in common that Rory and I don't? Who would that be, the Talbotts or that senior partner at Deloite and Touche?"

"You know what I meant. It's always best to tell each other major life events so that there's no awkwardness," Emily returned, taking a bite of her roast.

Rory coughed. "Well, then…I probably also failed to mention that I'm seeing someone else."

Richard perked up. "Really? Who?"

"Jess."

His eyebrows furrowed.

"Jess. Luke's nephew. From the diner?" Lorelai offered.

Richard frowned and turned his attention on Lorelai. "The one that broke her arm? You're letting Rory date him?"

Rory dropped her fork with a clank. "Hey. Don't blame Mom for this. I want to date him and he's a good guy. You'd like him."

"Well, then. Let's meet him," her grandmother suggested.

Rory faltered. "Umm, what?"

Emily smiled. "Bring him to dinner next week. It sounds like you two are getting serious…I want to meet the guy who my granddaughter is so enthralled with."

"I guess," Rory stuttered, giving her mom a pleading look. "He might actually have to work, but I'll see what I can do."

Richard nodded, satisfied. "Good, good." He took a bite of his meat. "Emily, does this taste a bit dry to you?"

Emily frowned and tasted her own. "Actually, it does." Rory and Lorelai let out slight yelps when Emily suddenly shouted. "Maya?"

They heard the quick footsteps of the latest maid rushing into the dining room.

"Yes, Mrs. Gilmore?"

Lorelai turned to whisper in Rory's ear. "I give it five minutes before she's fired."

Rory bit her lip. "Ten. Grandma's in a good mood now…forcing Jess to come like that."

Lorelai grinned. "It was gonna happen-"

The shrill voice of Emily Gilmore cut her off. "I want you out by tomorrow, Maya. Can't you do anything right?"

Lorelai rolled her eyes. "I guess we were both off."

Rory nodded.

-

-

-

Lorelai threw her coat on the couch as she and Rory walked into their house later that night. "Now that was a pleasant dinner."

Rory frowned. "Oh, yeah." Beat. "I have to talk to Jess. Maybe we can find a way to get him out of it?" she suggested.

Lorelai snorted. "Sure. You get right on that."

"It's not gonna be too bad." She bit her lip and sat down next to Lorelai on the sofa. "Hey, Mom?"

"Hey, Rory." She smiled. "What's up?"

Taking a deep breath, Rory began. "I told him I loved him."

Lorelai froze. "You told…love…who?" she choked out.

"Jess."

"Just like that? 'I love you'?"

Rory half-smiled. "Well, no. He kinda said it first."

Lorelai's eyes widened. "Wow."

"Actually, we were having the talk…you know, about it…and he said, and I quote, 'I think I might love you'."

"You were talking about," she coughed. "Sex?"

Rory frowned. "Yeah. You said we probably should, right…and so I brought it up."

"And you love him?" Lorelai looked almost a little scared.

A grin took over Rory's face. "Yeah. I love Jess."

"Wow."

"Haven't we been through this already?" Rory asked.

Lorelai shook her head. "Yeah, sorry. Just…it's big. I mean, you couldn't say it to Dean, and now…Jess." She cocked her head. "How is it different?"

Rory tucked a piece of hair behind her ear. "He's so…he's different," she concluded. "Like…he's smart and funny, and nice and everything." She paused. "He's actually a lot like you if you really get to know him."

Lorelai snorted. "Like me?"

"Yeah…I mean the sense of humor, the sarcasm, likes good music, smart, independent, strong. And he doesn't let many people in." She explained this all a little excitedly, just realizing how much truth was in what she just said.

Lorelai wrinkled her nose. "Really?"

Nodding, Rory grinned. "Really. Maybe that's why I like him so much?"

Lorelai laughed. "I'll take that as a compliment, thank you."

"As you should." Rory chuckled. "I can't believe I never realized it before," she admitted, thoughtfully.

Lorelai patted her leg. "Hey, no biggie." She bit her lip. "So, let me get this straight. You were talking about sex…and it segued into love?"

"I guess…"

Lorelai rolled her eyes. "And…" she probed for more.

"What?" Rory asked, truly not seeing what she was getting at.

"Sex…how'd that talk go?"

Rory shrugged. "Okay, I talked, he talked, I cried…that kind of thing." She tried to brush it off as nothing.

Lorelai frowned. "Why were you crying? Did he say something or-"

"No, not at all," Rory cut her off. "I just feel…inadequate, maybe? After he told me about his experience…I dunno…it was kind of silly when I think about it."

"His experience," Lorelai began hesitantly. "What exactly…"

Rory shook her head. "It's not anything big…he's had sex with a few girls…and he was pretty young, but…like I said before…it's not a big deal."

"Are you sure you're okay with it?" Lorelai placed her hand on Rory's arm comfortingly. "Jess and all the other girls?"

Rory nodded, giving her mom a small smile. "Actually, I am. It really doesn't bother me. I knew before we were dating that he wasn't a virgin…and that's not a big deal. Not many guys are…"

Lorelai grinned, trying to break the tension. "There are some benefits of dating an experienced guy, ya know."

At Rory's bemused look, she continued. "They now all the secrets of how to please…"

Rory giggled and hit Lorelai with a pillow. "Mom!"

Lorelai laughed. "C'mon, Rory…you know you can't deny it."

-

-

-

"Do you love it?" Rory smiled at Jess, who was scanning the back cover of a book.

"It's great."

Rory's voice rose in excitement. "The Holy Barbarians. I mean, what a title!" She grinned. "And it's by a Venice Beach beatnik about Venice Beach beatniks, and to top it off, the beatnik who wrote it is the father of the guy that does those Actor's Studio interviews on TV!"

Jess quirked an eyebrow. "The guy with the beard?"

Rory nodded. "Yeah, the pointy beard. That's his dad writing at his desk."

"Oh, it's weird that a weird beatnik-y guy would have a conservative son like that."

"Maybe he's not that conservative. Maybe at night, he, like, takes off his clothes and parties."

"Aw, man, now get that picture out of my head," Jess cringed.

Rory rolled her eyes. "It's a cool book, you've gotta admit."

"It is," he agreed. "Thanks."

Rory frowned. "Oh, I'm not lending it. I'm not done." She shook her head fervently.

He brought his eyes to hers. "Well, why'd you show it to me?"

"I like showing you the stuff I'm reading," Rory explained, as if it was obvious.

"But you knew I'd wanna read it. You're a book tease," he accused.

"You'll get it when I'm done," Rory promised. He reluctantly handed her the book.

Jess smirked. "Cruel woman."

She ignored him. "So, are you going to work now?"

Jess sighed. "Back to the salt mines."

"So, you're not tied to the hours you have, right? You can trade if you want to," Rory asked hesitantly.

"There's some flexibility," he told her. She could hear the question in his voice.

"You got any flexibility next Friday night?" She gave him her most charming smile.

"Yeah…why?"

Rory bit her lip. "I thought maybe you could come to dinner with us."

"Us?"

"To my Grandma's," Rory clarified.

Jess smirked. "To meet your grandmother," he concluded.

Rory nodded, offering him a placid smile. "Yeah, she'll be there, so yeah…it might be rude not to introduce the two of you."

Jess backtracked. "I can't, I gotta work."

"You just said you could get out," she pouted.

"I didn't know what for," he said, shaking his head.

Rory resorted to the begging-slash-whining tactic. "Jess…"

"No," he refused.

Rory frowned. "But I already kind of agreed."

He sighed. "Aw, man."

"So I'm kinda jammed here."

There was a small pause. "Does she know what I look like?" he asked.

"I don't think so."

"Perfect," he said. "Find someone who vaguely resembles me. Take him. Just don't kiss him goodnight."

"That's not going to work." She rolled her eyes.

"Andy Warhol did it all the time." Rory handed him the book. "We're just five bucks away from a deal."

Rory leaned in for a kiss. A few moments later, she tilted her head. "That's worth five at least."

"You Gilmores think a lot of yourselves." She gave him a hopeful smile. "Okay," he sighed.

"Thank you, thank you, thank you," Rory gushed.

He wrapped an arm around her waist. "Manipulator," he teased.

-

-

-

Rory dropped her backpack unceremoniously onto the floor beside the stool she just took a seat on at Luke's Diner. She was absolutely exhausted after a long day of school, but she was thanking all the gods she could think of, that it was Friday. She could finally relax, after a hopefully quick dinner at the Grandparents, and then spend a nice weekend with her mom and Jess…

She groaned and let her head fall to her hands at the counter. Jess. Dinner. Grandparents. Bad.

Just as she was about to continue her little rant, Luke walked over to her with a pot of coffee. He hadn't even need to ask before Rory nodded her head furiously, desperately pointing to the empty mug in his other hand.

When he was done pouring the hot liquid into her cup, she hastily grabbed it and downed half of the coffee within a few seconds.

Luke shot her a slightly concerned look as he was passing to the back of the counter. "Are you sure you're okay?"

Rory set down the mug and gave him a weary nod. With a small smile, she explained. "I just remembered about the dinner tonight. Jess and Mom and Emily and Richard Gilmore." She shook her head. "Not fun."

Luke raised an eyebrow. "Jess is going to Friday Night Dinner with you?"

Rory's face took on a puzzled expression. "Yeah…did he not tell you?"

He snorted. "Jess and I have the type of communication where everything is on a…need-to-know basis, I guess." He frowned. "And I guess this wasn't something he felt I needed to know."

"Hey, it's probably nothing. Maybe he forgot?" She offered hopefully.

He brushed it off, and his face lost the confused look it previously held. "Nah, it's not important. No biggie. Anything else you want to eat?" He changed the subject as subtly as he could.

She grinned. "Ah, nothing now. I'm a little bit too nervous to eat anything."

Luke nodded. "Okay. Don't hesitate to call me over if you want anything. You waiting for Lorelai?"

"Nope," Rory said, finishing the last of her coffee. "She has to work a little late. She's just heading straight to Hartford from there. I'm going with Jess."

"Okay…" He frowned. "And Lorelai's okay with it…with the accident and stuff?" He sounded a bit uncomfortable with this conversation, probably remembering the resulting blow-out her had with Lorelai because of it.

Rory shrugged. "She's…dealing with it. She like's him than she used to; or at least tolerates him." She shot him an amused smile. "Is he here, by the way? I wanna make sure he's gonna be ready…"

Luke cut her off. "Upstairs, I think. Go ahead."

Rory gave him a grateful look before scooting off the bench and over towards the curtain leading to the apartment. She reached the top and knocked, waiting a few seconds before Jess opened the door.

"You know, you could have just walked in." He greeted her with a small kiss before leading her to the couch. He picked up the book lying next to him and marked the page before sitting down with her.

She rolled her eyes. "It feels weird, I guess." She smiled when she caught the title of the novel. "Is that The Holy Barbarians?"

He smirked. "Yeah. I'm about halfway through."

Rory gave him what she hoped was an innocent smile. "Speaking of the book, you know what tonight is…"

Jess groaned. "Unfortunately. I still think you should go with the method I suggested earlier. Much cleaner."

"But what if they meet you again at some other social event, and see me with you and think I'm cheating on the real Jess, who'd actually be the fake one, with you, who'd really be the real one?"

His eyes widened. "Where the hell did that come from?"

She gasped. "Oh, God…I'm turning into my mom." She sat up, alarmed. "And my grandma!"

He cocked his head to the side, confusion evident on his face. "I see your Mom in there, but…your Grandma?

She shook her head thoughtfully. "Last week she was going on about how it was terrible of me to not tell her Dean and I broke up because they might see each other at a social event for a mutual friend."

"Dean and your grandma have mutual friends?"

"Exactly what I said," she exclaimed. "I mean, it makes no sense…but, hey…that's Emily Gilmore for you."

Jess just sighed. "Can't you tell how excited I am to meet them?"

"You look ecstatic," she deadpanned.

He let out a dry chuckle. "You so owe me for this."

She reached over the sofa and gave him a small kiss. "I promise I'll make it up to you."

Jess grinned as he pulled back. "Yeah?"

"Yeah." She brushed her lips against his one last time before jumping off the couch and heading towards the door. "Pick me up in an hour."

Rolling his eyes, he nodded. "One hour."

-

-

-

Rory threw everything she needed into her purse right as she heard the sound of a car honking in front of her house. Cursing under her breath, she slung the bag over her shoulder, grabbed the pair of heels by her door, and almost tripped to the front of the house. She sighed as she went outside, shutting the door behind her.

"Coming, coming!" she called, waving to Jess, who looked a bit uncomfortable in a pair of slacks and a collared shirt. He was standing outside the car, leaning against the side.

As Rory reached the car, she grinned. "You look nice."

He greeted her with a kiss. "You do, too. Ready to go?"

She nodded. "Yup." Throwing a smile over her shoulder, she went over to the passenger side, and scooted into the seat.

Jess watched her for a second before getting in himself, and turning the keys. As he pulled out of the driveway, he turned his head towards Rory. "Lorelai's meeting us there?"

"Yeah," she confirmed. "She had to work a little longer at the inn."

He nodded. They drove in a comfortable silence for awhile before Rory bit her lip, and rested her hand on his thigh.

He raised an eyebrow. "What's up?"

She offered him a small smile. "I just want to warn you…my grandparents can be kinda scary."

He laughed. "They can't be that bad."

"Oh, they're that bad." She sighed. "Don't say anything to offend them, or their lifestyle. Don't mention anything about you smoking or drinking…just-"

He cut her off with a smirk. "Just don't be me?"

"No, no, no." She hastened to fix what she said. "I just mean…be boring, I guess?"

Jess rolled his eyes. Rory cocked her head to the side, thoughtfully. "Mention reading to my grandpa, maybe…and with my grandma…she's harder, I think."

They were almost to the Gilmore's house. He pulled off the interstate and onto a smaller road. "It'll be fine, Rory. How bad can it be?"

"How bad can it be?" she muttered, shaking her head. "You ain't seen nothin' yet."

-

-

-

"Ring the bell."

Jess raised an eyebrow at Rory as if to say, 'Me?'

Rory nodded. "Yup." She pouted when he refused. "Please?"

He rolled his eyes. "Let's wait for your mom. That way your grandma might not realize that you drove her in a car with the guy the broke your arm."

"Fractured," she reminded. "And maybe that's a good idea." Her voice was sheepish.

He grabbed her hand and led her over to the steps in front of the door. Rory leaned into him as they sat down.

"How long 'til she gets here?" he asked.

They heard a car pull up into the driveway. Rory grinned. "Great timing."

Jess shook his head and stood up, pulling Rory into a standing position next to him. They waited as Lorelai shut off the jeep and got out of the car. She waved towards them, slinging her purse over her shoulder as she walked up to the front door.

"Hey," she greeted. "Whatcha' waiting for?"

Rory motioned to Jess, grinning. "You. He was afraid."

Jess protested. "Was not."

"Was too."

He glared. "Was not."

"Was too," Rory giggled.

"Was n-"

Lorelai cut him off. "As much as I'd like you to continue this weird argument-like thing…we have to go in. We're gonna be late."

Rory smiled, wrapping an arm around Jess' waist and leaning up for a kiss. "Sorry," she said.

Jess rolled his eyes. "Yeah, yeah."

Lorelai sighed and pressed the doorbell. "I suggest you separate before Emily comes and sees you."

The reluctantly stepped away from each other right as the door opened. Rory gave her grandmother a grin. "Grandma…good to see you."

Lorelai nodded, smiling tightly. "Mom."

Emily grinned. "Rory, Lorelai…Jess, is it?" He nodded his head. "Come in, come in."

She called for the maid. "Maya! Get their coats please!" Rory and Lorelai exchanged amused looks as they heard Maya's feet rushing from the kitchen."

"Yes ma'am, Mrs. Gilmore." She bowed lightly before taking everyone's jacket and walking them over to the closet.

Emily clapped her hands. "Well, then. Drinks?" She led them into the living room, where Richard was reading the paper.

Lorelai sat down on a chair, giving Rory a look that said, 'Going better than I expected.'

Rory nodded, and sat next to Jess on the long couch. She leaned into his side, getting comfortable.

Emily's overly cheerful voice broke through the silence. "Lorelai, what would you like to drink? Rory, Jess, Richard?"

"I'll have a martini," Lorelai said.

Richard set down his paper and looked up at his wife. "That sounds like a good idea. Martini for me, as well."

Emily nodded and turned to the teenagers. Rory smiled and motioned towards Jess. "We'll both have water."

She turned back around and made the drinks. On her way to handing Richard his drink, she shot Lorelai a glare.

Lorelai rolled her eyes and gave Rory a significant look. 'Well there goes that…' she thought.

She took a sip of her martini as Rory and Jess were handed their waters. Emily sat down next to her husband, setting down her own drink on the coffee table in front of her.

"So, Jess," she started. "Lorelai tells me you work at the diner. Does it feel less important that you only work there because your uncle owns the place?"

Rory made a move to protest, but Jess beat her to it. "Nope. Feels just fine."

Emily nodded tightly, returning to her drink.

Richard frowned, setting down his glasses. "Jess…what are your interests?"

Taking a deep breath, he leaned forward. He told Rory he'd make an effort… "I like reading a lot…sometimes I write. Music is always good, too."

"What kind of books do you like?" Richard asked, his expression curious.

"I'm a big fan of Hemingway…Tolstoy, any of the classic writers. I do like modern books as well, though."

Richard smiled. "I actually have a first edition Old Man and the Sea in my study…maybe I could show it to you sometime?" he offered. He liked this boy, so far, from what he saw. Definitely smarter than the last one.

Jess nodded, giving him a half smile. "That'd be great."

Emily frowned, not liking the fact that Richard was getting along with this…hoodlum. She decided to intervene. She gave Jess a fake smile. "Jess…do you drink?"

He snapped his head up at the seemingly random question. He was internally debating whether he would answer at all…and if so…what to say. He took one look at a nervous Rory and chose. "I have." Honesty. He just hoped it was the right choice.

Richard lifted his head as Lorelai shut her eyes, knowing what was coming. She leaned back in her chair and said nothing. Rory was nervously fidgeting with her fork; her eyes darting from her grandma to Jess to her grandpa and back again.

Emily continued. "That's good. Do you smoke, too?"

Jess smirked…it was on. "I did."

He heard someone inhaling deeply from across the table, but didn't avert his steady gaze from Emily's eyes.

"And what about sex?"

Lorelai groaned, dropping her head against the table. Richard lifted a hand…"Emily…do you think this is fair? Maybe you could tone it down a bit…"

Emily gave him a polite, tight-lipped smile. "Don't you want to know what kind of guy you granddaughter is spending so much time with?"

Jess spoke up, answering the previous question, smirk still in place. "I've got no problem with sex."

Emily faltered. "I was asking if you have sex."

Jess feigned innocence. "I'm sorry. My mistake. And yes, to answer your question. I'm sure as hell not a virgin."

Rory squeaked as the table went into an uproar.

"Emily…this is not appropriate dinner talk."

"Why are you so fond of him, Richard?"

"He's a good kid. You can't tell me that when you were a teenager, you were perfect."

"No, not perfect…but I had morals. I was respectful towards adults and…"

Lorelai interrupted her parent's argument. "Mom, Dad…maybe we should just go. Sorry for the…just…sorry."

Rory set her fork and knife down, standing up. She tapped Jess on his shoulder, motioning for him to get up as well. "Let's go," she whispered in his ear.

He nodded, scooting his chair back and standing. "Nice to meet you Mr. Gilmore. Maybe you can show me that book another time." He offered his hand.

Richard shook it from across the table. "You too, Jess. I'll get in contact with Rory so we can set something up."

Emily threw her hands up. "This is unbelievable." She stomped out of the room, her heels clacking against the floor. Everyone stared after her, frowning.

Richard apologized. "I'm sorry for her behavior. She's just worried about Rory. She'll warm up to you eventually," he assured Jess.

Jess held back a snort. "I wouldn't count on it," he muttered, under his breath. Rory heard him and slapped his shoulder.

She gave her grandfather a hug before reaching for Jess' hand and making her way towards the door. Lorelai was waiting there, holding everyone's coats, a slight, 'I told ya so' expression on her face.

Rory rolled her eyes and grabbed her jacket, handing Jess his, as well.

Lorelai raised her eyebrows. "So…we're off…"

They nodded and followed Lorelai to the car in a slightly awkward silence. Lorelai turned to the tow teenagers walking at a slower pace behind her. "Rory…are you gonna ride with Jess or with me?"

Rory looked at both her mother and her boyfriend, unable to decide. She noticed that Jess looked a bit more…morose than usual…and figured that maybe he thought she was mad at him or something.

Her decision was made. Giving her mom an apologetic smile, she told her that she was going to go ahead with Jess.

Lorelai nodded, telling them to get straight home, and they agreed quietly.

She left in her car, throwing one nervous, backwards glance in their direction on her way out.

Jess sighed. "Ready to go?" He was leaning against the side of the car, much like he had been earlier that evening, but his expression was decidedly less cheerful.

Rory nodded, smiling slightly. "Yeah," she said quietly, matching his tone.

They each proceeded to their separate sides of the car, getting situated. He was just putting his keys in to turn the car on, when she stopped him. "Jess."

He hung his head before raising it a little to meet her eyes. "Yeah?"

She frowned when she noticed the lack of emotion in his voice. He sounded deflated. "Jess…" she prodded again. "What's wrong?"

He sighed and let his hand drop from the dashboard. "Nothing."

She pursed her lips at his stubbornness. "Jess, c'mon. Tell me what's bothering you."

"I'm sorry I said all that stuff."

Rory tilted her head. "You think I'm mad, don't you?"

He shrugged noncommittally. She put her hands on his shoulders, turning to face him. "I think you handled it well." She snickered. "At least the dinner went a little better than Dean's."

He almost cracked a smile at this. "Huh."

She grinned. "Yeah…and my grandpa really seems to like you…even after all that stuff. I can't believe he defended you…it was the complete opposite with Dean…Grandpa hated him."

Jess' face held a full-blown smirk by now. "That's cos' your grandpa has brains," he pointed out.

Rory nodded, still smiling. "I'll tell him you said that. But you do know I liked Dean at one point."

Jess grinned. "I'll forgive that little mistake in judgment on your part."

She playfully punched him in the arm. "Shut up."

"Ready to head back home now? Mom'll freak if you don't get me back soon."

Jess sighed, nodding. "You're probably right."

"I'm always right," Rory said proudly.

Jess snorted. "And I'm the queen of England."

A/N: Yeah...that was long. :D Sorry for the wait...I really am. I just got my wisdom teeth pulled...and was loopy on narcotics for weeks...and then I went on vacation...so...here it is. :) Finally. :P

Reviews would be great...like...shirtless!Milo great. So...review...and I get the greatness equivalent to shirtless!Milo. I want it...and I always get what I want. No...I'm just tired...and it seemed to fit...but review away.

OH! New thing! I've decided to start responding to all signed reviews...so if you have any suggestions or questions or ideas...review with 'em. :D

I think that's finally it...Review...and the new chapter will be out. :P