AN: This story takes place around the time of episode 3.19, Keg! Max!, but some major details have changed. Things are happy in Literati-land, Jess is graduating, and a new character (from a conceivable alternate universe) comes to town.

The sun streamed in the bank of windows, alighting on all that surrounded him and Jess was in a good mood. He was off work in fifteen minutes and he couldn't wait to take a book down to the park and lie on the burgeoning grass, to bask in the warm sunshine of a truly promising spring.

Jess was busy arranging the salt and pepper shakers on the table he'd just wiped when the door chimed behind him. Jess sighed, seeing his fifteen-minute-window threatened. It would be a lot harder to get out of work when he had a paying customer.

He hoped with all his might that all the person wanted was a single cup of coffee. To go.

Jess turned around to face the intruder. Immediately his sight fell upon a head covered in a crop of ash brown hair. Stylish clumps of white blonde framed a familiar face. He frowned. "What are you doing here?" he asked.

"I came to see you. Obviously," the girl replied.

"You did?"

"I didn't come for pie. Aren't you glad to see me?"

Jess shook his head as he snapped out of his surprise. "Sure. I guess. What's up?"

Cady pulled out a chair at a table between them and sat down. She watched Jess until he sat down too.

"What's up?" he repeated.

Cady took a deep breath and jumped right in. "Come back to New York."

"No. Why?"

"I want to live with you. Let's get a place together."

"In New York?" Jess asked, annoyed.

"Yes."

"No," he replied abruptly.

"I've got a job. I can help pay rent."

"What about school?"

"You're one to talk."

"I'm graduating in a month. I've been going."

"Pfff!" Cady dismissed, and Jess had to admit she had a point. He didn't exactly have the best track record when it came to school attendance. He'd only really been going since Luke had recently laid down the law.

But he repeated, "I've been going. Have you been going?"

She didn't answer him. "Please, Jess. I can't live on my own and I can't live with her."

"What did she do this time?"

"Nothing." The girl shook her head and looked down at the table. Cady toyed with and then accidentally knocked over the salt shaker. Jess glared at the sprinkles that fell out onto the sunlit table. He'd just cleaned this table.

"She must've done something."

"Nah."

"Then what did you do?"

"Nothing!" Cady exclaimed, as though hurt. "We just have a difference of opinion."

"Uh huh," he said, humouring her.

She tried a new tactic. "Don't you miss New York?"

"I'm not leaving Stars Hollow."

Cady laughed. "Why? It can't be the thriving nightlife."

"I've got a good thing going here."

"What's that? Working in Luke's Diner?"

"I've got a girlfriend."

"You? You have a girlfriend. Like a long-term thing?"

"Don't look so surprised." He forcefully uprighted the salt shaker and gathered the salt sprinkles into his hand. Looking around for a suitable receptacle, and not finding one, he dumped the crystals onto the floor with increased annoyance.

"But you're so Love 'em and Leave 'em."

"I am not."

"Well you never cared about a girl before."

"Whatever," Jess dismissed.

"Well did you?"

Jess took a laboured breath, then answered with squinty eyes, annoyed as she finally got to him. "I don't know," he muttered defensively.

Cady smirked at him. "I knew it."

"You don't know anything."

"Don't pull the age card on me again. You're only three years older than me."

"I wasn't pulling the age card."

Just then, a flannel-clad man emerged from the store room. As he breezed past their table, he did a double take and then took two steps backwards. "Cady! Hi."

"Hey, Uncle Luke."

"Were we expecting you?"

"No, surprise visit."

"How are you doing?"

"Good."

Luke paused to elicit elaboration which never came. Cady just slouched in the chair and looked up at him. So he went on, "How's your mom?"

"Good."

"How's school?"

"It's there."

He adjusted his ball-cap with his palm and tried a new tactic. "What are you up to these days?"

"Not much."

"And your mom?"

"The same," she said sweetly.

Luke looked between Jess and Cady as a silence ensued. Growing slightly uncomfortable, Luke finally spoke. "Well. It was good catching up. We should do this again."

"Great."

Then Luke shook his head and began to walk away, muttering something about the conversational skills in the gene pool.

When Luke was safely out of earshot, Cady continued, "Come back to New York."

"No."

"Please, Jess."

"Why?"

"I want to live with you. But not here."

"No."

"Jess, you're eighteen. You can live wherever you want. I can't yet."

"I am living where I want."

Cady drummed her fingernails on the table as her eyes trailed around the room, from the kitschy decorations behind Jess's head to the No Cell Phones sign and the cubby holes dotted with oddly shaped mugs. Even the table she drummed upon was kitschy, as it didn't match any of the other tables in the place. "Here?"

Jess shrugged.

"Have you seen this town?" she asked, gesturing out the window. "Do you want to know what I saw on the way in here?"

"Was it the family in the matching jogging suits? Because I saw that on the first day."

"I'm sorry, but you in this town does not compute."

Jess grew tired of this line of conversation. The sun was descending in the sky and his book was calling out to him. "What did she do?"

Cady pursed her lips.

"I know this is about her so tell me what's going on."

Cady sighed and toyed with the laced-up arm band at her wrist. "She won't let me date."

"What?" Jess chuckled. "Why not?"

"She says I'm too young."

Chuckling still, he replied, "You're fifteen."

"Exactly. She says that's too young."

Jess thought back upon his youth and puzzled. He had certainly been dating when he was fifteen. "It's not too young. She let me."

"Well I guess she's got a double-standard then."

"Lizzie's as lax as they come. What's wrong with the guy?"

"What?"

"What's wrong with the guy?" he repeated more forcefully, enunciating each word.

"Nothing. He's a great guy."

"But…?" he led.

"He's twenty."

"He's older than me?" Jess cried out.

"Yes."

Jess did the math. "He's five years older than you?"

"Yes."

"God, Cady!" Jess shuddered in revulsion at the thought of someone more experienced than him touching his baby sister. He could imagine exactly how Liz felt about this turn of events. "I don't blame her."

"Don't play the age card again. I don't need you to protect me."

"You came here to ask me to play the age card! You came here because I'm eighteen and I can legally take you in. You wanted me to protect you. It's exactly the card you want me to play!"

Cady rolled her eyes, but she had no argument. "She won't let me see him."

"I don't blame her. Neither would I."

Frustrated, Cady grunted and glared at the row of stools at the counter.

"A five year age difference. At your age, that's just gross." Then Jess nodded, deep in thought. "And probably illegal."

"No."

"He's too experienced."

"He's not."

"Oh, God," Jess worried. "Are you that experienced? You're fifteen!"

"Oh please, Jess," Cady scoffed. "Don't give me that. You were fifteen. You brought enough girls around the apartment."

"No."

"I was there, Jess. I heard it all."

"You heard nothing."

"Don't tell me what I heard. I know what I heard."

"I can promise you, you didn't hear what you thought you were hearing." Jess rearranged the items on the table. They were no more neatly placed now than they had been before, only differently situated.

"I know what I heard."

"No. You don't."

Cady chuckled, annoyed. "I'm not some naive child. How can you say that?"

Jess sighed. "Because it never happened. I've only just recently... With my girlfriend." Jess pursed his lips and took a shaky deep breath. This was definitely more than he'd planned on revealing.

"You're kidding."

"I'm not."

"What the hell Jess?"

"What's that supposed to mean?"

"You had me thinking you were so promiscuous."

"You thought that on your own. I didn't tell you to think that."

"What would you have had me think then?"

"That it's none of your business and you shouldn't be comparing yourself to me anyway."

"What about Stacey? You never boffed Stacey?"

"Jesus Christ! Don't say that!"

"I heard you two. Whenever Mom was at work. You can't tell me you never boffed her."

"I never boffed her." Jess rolled his eyes. Then he shrugged his shoulders. "We took turns."

"What?"

"Do I need to spell it out for you? If you're so experienced, you can figure it out."

Cady eyed him closely and Jess could practically see the gears turning. "What? Just oral? You just used your mouths?"

"Yes," Jess hissed. He took a quick appraisal of the diner for good measure. Of course there was no one else there, but he knew Luke was right in the next room. He muttered, "And hands or whatever. Can we not talk about this here?"

Cady leaned forward and whispered. "Are you telling me you were a virgin until you came here and met your girlfriend?"

Jess sighed, wearied. "That's what I'm saying."

"Are you lying?"

"I'm not lying."

"You had girls over all the time."

"We were curious," Jess offered, by way of explanation.

"Oh my God." Cady sat back in her chair and shook her head incredulously. "My Brother, you just blew my mind."

In spite of himself, Jess breathed a short laugh. "You sound like Mom when you say that."

"Bite your tongue."

Jess grinned and rubbed the salt into the wound. "You, with the whole 'My Brother' bit. It sounds just like her."

Irritated, Cady deftly sidestepped her brother's taunting. "You never had sex with those girls?"

"It depends on what you define as sex."

Cady cocked her head to the side and fixed him with a withering stare. Jess matched the glare with one of his own.

Finally he shrugged. "No. I never did. I didn't want to get them pregnant. I didn't want to keep them in my life. I wanted an easy out."

"Wow. Touching." Her voice dripped with sarcasm.

He disagreed. "Prudent."

She shrugged, in defeat. "Yeah."

"So…" he began softly. "Are you that experienced?"

Cady stared back at Jess and it was all the explanation he needed.

Frowning, Jess continued, "Were you at least safe? You're not pregnant, are you?"

"No."

Jess raised an eyebrow at her.

"I mean, yes, we were safe and, no, I'm not pregnant. Don't ask two questions in a row if you expect them both to be answered."

"I'll talk to Luke. Maybe you can stay here."

"I don't want to stay here."

"I don't want you going back to your twenty-year-old."

"His name's Adam."

"Whatever."

Irritably, Cady jumbled up the items on the table that Jess had meticulously straightened. This offer of a life in their beloved New York was not going as planned. Since when had Jess become so straight-laced and meticulous? Here he was, living in this tiny town, working in his uncle's diner—going to school—and sitting in front of her now, seeming so content with the mediocrity of it all? She gave him another appraisal. Gone even was any black cotton, death metal t-shirt, gory and offensive, once such a staple in his wardrobe. In its place was a long-sleeved, button-down work shirt, vaguely western in its detailing. Cady had never seen Jess in a button-down collar before, nor crosshatch pinstripes. The view of it now didn't sit well with her at all.

"You've changed Jess."

"Yeah, and you will too by the time you're eighteen. Especially by the time you're twenty."

"And what's this 'talk to Luke' business? What's happened to you?"

"Nothing and everything."

"That's cryptic. Look can I live with you or not? If not, then I'll just have to make other plans."

"What? Are you gonna go live with him?"

"Maybe I will."

Jess's eyes narrowed as a thought occurred to him. "You don't want to live with him."

"Yes I do."

"Don't give me that shit. If you wanted to live with him, you wouldn't be here begging me to move back to New York."

Cady shrugged.

"What's going on?"

"I can't live with him. He's married."

Jess smacked the side of his head. Shaking his head incredulously, he raked fingers through his hair. "Holy shit!"

"I love him."

"Cady, do not go back to this guy. He's obviously a jerk. Come live here with me. I'll talk to Luke, maybe we can make it work upstairs. If not, then you and I will find our own place. But not in New York. Here. Far away from that jackass."

"No, Jess."

"I'll introduce you to some people. My friend Derek's got a brother. Surely there's someone at my godforsaken high-school that will appeal to you!" He looked at her pointedly. "And not a teacher either!"

Cady smirked at him.

Jess leaned forward and placed a palm over Cady's hand. "Please don't go back to this guy. He's a dick. Guys are dicks. I should know."

"You're not a dick."

"Yeah I am. I've had eighteen years of practice at it. And this guy's got two years up on me."

"He's not a dick."

"He's a cheater and a statutory rapist. If you don't move here to Stars Hollow I'm gonna have him arrested."

"No! You wouldn't." Her kohl-lined eyes opened wide.

"Wouldn't I?" Jess challenged.

"That's blackmail!"

"Huh. So you have been doing your homework."

"He's not a rapist. He didn't force me."

"Statutory rapist. It's when the victim is a child. Physical force isn't necessary."

"I'm not a child."

"Do you have any idea how young fifteen seems? Even to me? I remember fifteen and it was a long time ago. To him, you are a child. Please. Let me introduce you to Derek's brother or anybody else. Please."

Cady smiled finally and placed her palm above their stack of hands. "I've missed you, My Brother."

Jess smirked. "You're doing it again."

"That time it was on purpose."

They sat in companionable silence for a while. Jess felt the precious daylight ticking away but suddenly he didn't care quite so much.

Finally Cady spoke, "Adam's always pulling the age card on me also."

Surprised by her admission, Jess blurted, "See? Isn't that gross? He's too old for you."

"Maybe."

"And he's married. You can't have him."

"I know."

"I hate to point it out but… falling for a guy you can never have… is very Liz."

"Bite your tongue!"

"Tell me it's not."

Cady just glowered at him until he laughed.

Several minutes later, Jess was happily leaning into the table when he became aware of a shadow falling across it. The reflection from the school's window no longer streaked sunlight across the Formica surface. Jess turned his head to look out the window beside them. Rory stood there, her mouth agape.

Surprised for a moment, Jess sat upright and raised his eyebrows. Then he smiled and nodded his head in the direction of the entrance, encouraging Rory to come in. To his sister, he added, "This is her. This is Rory."

With zombie-like fortitude, Rory turned from the window and found herself at the door to the diner. Cady's eyes followed her all the way to their table.

"Hi there," Cady offered enthusiastically.

"Hi," came the cautious response, as Rory stood beside the table. Her eyes dropped down to their interlocked hands.

Jess eyed his girlfriend with curiosity, then raised his eyebrow as a thought occurred to him. "Rory, this is my sister. Another quality product of Jimmy and Liz."

Cady's head snapped back to Jess. "Gross." She pulled her hands away and pushed meagrely against the table.

"That's how it happens. Or didn't you take sex ed?" Only Jess and Cady were aware of the inherent reprimand in his statement. She grimaced.

"Oh! Cady! Thank God!" Rory let out a visibly repressed gasp of air.

"I've never gotten that response before."

Jess smirked at Rory, knowing the answer before he even asked his question. "What? Did you think I was sitting here with another girl?"

Rory ignored him and stuck out her right hand. "Cady Mariano!" she cried enthusiastically. "I'm Rory Gilmore, Jess's girlfriend. It's so good to finally meet you!"

"Danes," the girl replied with a smile as she accepted the handshake.

"Hmm?" Rory murmured, unsure.

"Cady Danes. Jimmy was already long gone by the time I was born."

Embarrassed by her social blunder, Rory muttered, "Oh, I'm sorry. I didn't mean—"

"Forget about it. It's no big deal. Pleased to meet you too."

Now that Rory was already vulnerable—making her cute foot-in-mouth face—Jess's smirk grew and he repeated, "Did you think I was sitting here with another girl?"

"Yeah," Rory admitted sheepishly.

"I wouldn't do that."

"No, I don't suppose you would."

"Especially not in this town, with the rumour mill being as starved for a story as it is."

Rory stuck out her tongue as she sat down next to him.

"I'd at least take her to Woodbridge." To Rory's intense expression, he added, "I'm kidding."

Cady jumped in knowingly, with calculated intent. "He wouldn't cheat on you. In fact, he waited for you."

"What?" Rory looked from Cady's glowing eyes, to Jess's glowering ones.

"He saved himself."

"You're a brat," he admonished.

Smiling, Rory turned back to Cady. "What do you mean?"

"She doesn't know?" Cady asked her brother before turning back to Rory and feigning righteous confidentiality. "Ask Jess. He tells me it's none of my business."

"Okay. What does she mean?"

Jess chided his sister while watching Rory's animated face. "It is none of her business."

"Is it any of my business?" Rory asked.

"I suppose."

Rory's eyes were twinkling. "Then what does she mean?"

Jess wrapped an arm around Rory's head. Pulling her closer, he dropped a kiss upon the hair at her temple. Pulling away slightly, he whispered, "What do you think she means? You're probably right."

"Don't make me guess." Rory smiled again. "Something tells me this is too juicy not to hear first-hand."

Jess turned to his sister and exhaled purposefully through his nose. "You're dead to me."

"Just tell her. It's not that big a deal."

Jess irritably cleared his throat as his eyes bore down on Cady. Then he turned a sheepish glance to Rory. "You were my first."

"First what?" Rory asked, with a delighted twinkle in her eyes.

Jess rolled his eyes. He smiled and shook his head, to take the edge off his words. "You can be so dense sometimes."

"Mmm-Hmmm," she urged, amused.

"Lover," he finally explained.

"You're kidding. But you always seemed so promiscuous."

Cady chimed in. "I know, right?"

"What is with everyone saying that?"

Rory smirked. "Not even with Shane?"

"No. God!"

"'Cause you two were all over this town," Rory went on.

Jess rolled his eyes again.

"I'm pretty sure I told you two to get a room at least once. I'm just surprised you never did."

"Can we drop this?"

"And you had your car. You never went out 'driving'? I saw that bra in the back seat! You never? Not even then?"

"Uhh!" Jess cried, turning his head to the window and yearning for the park once again.

Rory looked at him closely. "I'm just saying… Lucky me." She grinned.

Turning his gaze tentatively back to Rory, Jess smiled discreetly and pulled her close again. This time his lips fell on hers.

"You two are so cute together," Cady said, interrupting their kiss.

"You're a brat," Jess repeated.

"I don't know. I think I like her!" Rory said. She and Cady shared a conspiratorial giggle while Rory reached for his hand and gave it a reassuring squeeze.

Jess sighed. "What am I going to do with you Cady?"

"What do you mean?" Rory chimed in.

Jess turned to his girlfriend. "She's fifteen and she's sleeping with a twenty-year-old man."

"Hey!" Cady protested. She pulled her sweater's wide neckline more snug around her shoulders.

Jess scoffed. "If my secrets are out, your secrets are out."

Rory ignored their squabble and interjected. "You're dating a twenty-year-old? I'm eighteen and I can't even see myself dating a twenty-year-old."

Jess took his eyes off Cady to peer at Rory. "I'm glad."

Rory quirked an eyebrow at him.

"At least until I'm twenty," he amended with a smirk.

Cady snorted. "I take back the cute comment, Brother. You're just embarrassing."

Jess frowned at his sister and added, "He's married also."

Rory was taken aback. "Married? You're dating a married man?"

"Sleeping with," Jess corrected.

"Wow. I definitely can't see myself with a married man," Rory whispered.

Cady scowled at the conversation taking place in front of her. She and Jess always vied for the upper hand and, right now, he was definitely winning. Then she grinned evilly and deflected the best way she knew how. She turned to Rory. "What about when Jess is twenty? Can you see yourself married to him?"

Rory grinned, first at Cady and then at the look of abject embarrassment on Jess's face. She was just opening her mouth to speak when Jess called out eagerly, "Hey Luke!"

Rory laughed instead.

In a moment, Luke poked his head out from the kitchen. "Yeah? Oh hey, Rory."

"Hey, Luke!" Rory replied cheerfully, still scrutinizing Jess with obvious merriment, as Jess tried his darnedest to dodge her gaze.

Jess went on to inform his uncle, "Cady's going to stay with us for a while, until we can get some stuff sorted out."

"Okay. You're always welcome, Cady," was Luke's gracious, familial reply.

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