A/N: Thanks so much for all the love for my story it means a lot! I have a question for my readers, i'm in the middle of a rewatch of Marvelous Mrs. Maisel (ASP's newer show) and i was thinking of writing a Midge/Lenny story, would anyone be interested in reading it if i wrote it? Please lmk!

When Jess left the diner to find Rory he searched for a while, he thought he knew where she'd be but he was wrong. So he stopped by the gas station and decided to wait to see if she found him. He took out his pack of cigarettes and looked at them, he'd realized he'd been smoking a lot less the more he'd been around Rory, he supposed it wasn't a bad thing but he didn't want to change who he was because he was dating someone new.

He took one cigarette out and looked at it while he used his fingers to flip it over a few times. He didn't notice that Rory was walking up the street so he was a little surprised when she spoke. "You going to smoke that or mind meld with it?"

"Depends."

"So this is what you had to do that was so important you had to leave Luke's in such a rush?"

He knew Rory was talking about the fact that he was doing nothing more than leaning against the wall but since his whole intention was to spend time with her and she was with him now he responded, "Pretty much."

"Hmm."

"And what about you? Isn't Lane's about four blocks that way?"

"Oh yeah, you know, it didn't seem quite as important after I left the diner."

Jess nodded "So."

"So."

"Here we are."

"Yeah, here we are." Rory looked down at the cigarette Jess was still holding "So tell me, what's your decision about smoking that depending on?"

"On what's going to happen."

"When?" Rory noticed that Jess' eyes kept flicking to her lips and it made the butterflies that had pretty much been living in her stomach explode.

"Now." Jess reached over and put his hand on Rory's hip and she shyly took a step closer to him before tentatively putting her hands on his chest. He leaned in and kissed her, Rory wrapped her hands around his neck and kissed him back.

She pulled back just enough to say, "I'm glad you didn't smoke it."

"Oh yeah?"

"Yeah." She leaned back in to kiss him again. The kiss was more than she'd experienced before. Of course, she'd kissed Dean before, and heck, Jess too but this was different, more passionate, it made her skin feel alive, on fire, tingly.

Jess slipped the cigarette into his pocket so that his hand could be free to wrap around her and pull her closer. When he finally pulled away it was just enough to rest his forehead against hers and grab her hands in his. "Well whatever else happens between us, at least we know that part works."

She smiled shyly at him, "Yeah."

"Oh, your mom hired me."

"She did?" She already knew her mom was going to ask him if he wanted the job but she didn't want to offend him or anything by making it out to seem that he needed money so she decided to act surprised.

"Yeah, apparently your gutters are in need of cleaning."

"You can say that again, you should have seen what came down with my mom as she fell when she tried doing it herself."

"Wow, way to sell it, now I can't wait to get up there."

Rory giggled lightly. "When are you doing it?"

"Not sure, she told me to come by tomorrow morning but on the walk over here I saw some interesting signs that caught my attention.

"Signs?"

"Yeah, signs, apparently this town is in need of another fundraiser, and the last one worked out pretty well for me so I figured why not?"

Rory knew what fundraiser he was talking about, she'd been looking forward to it all month. "Oh yeah, so you're thinking about going to the book fair?"

"I was considering it, if I, you know, had some company."

"Why Jess Mariano, are you asking me out on a date?" She couldn't help but think he looked cute because of how uncomfortable he looked right now.

"Well, yeah. I mean that's what people do, right? People who are, you know, like us."

"Like us?"

"Yeah, you know, dating or whatever."

"Oh my god, are you blushing?"

"Shut up." In a quieter voice, he continued, "This is all new to me."

That confused Rory, Jess did not strike her as the inexperienced type, in fact, that'd been one of her worries when she was considering dating him. "What do you mean?"

"I mean I haven't really ever been in a relationship before, this is all new to me and I don't have many stellar examples to draw off of. So you might have to cut me some slack because I'm sure I'll get things wrong but I'll try, and I'm a fast learner."

Rory felt her heart break a little bit, he seemed so worried, and earnest too, she had the feeling that he had no clue what he was doing but he'd work hard to get it right and that was all she could ask for.

"It's okay Jess, we'll figure it out together. And yes, I'd love to go to the book fair with you."

"Cool. Do you think your mom will care if I come over on Sunday instead?"

"No, she'll be fine with it. But I'll ask her to be sure. Oh…"

"Oh? Oh, what?"

"Oh, I forgot to tell you."

"Tell me what Ror?" He sounded annoyed now since it was clear she was avoiding telling him whatever she wanted to tell him.

"She knows."

"Jeez Rory, what does she know? If we're playing 20 questions I think you're missing the point of the game."

"She knows about us, about New York, skipping school, meeting Carmin, all of it."

"Oh."

"Yeah, oh."

"So what? Does she hate me now?"

"What? No! Why would you ask that?"

"I don't know, I'm the bad boy, the rebel without a cause, isn't that what you called me? And you're the precious perfect daughter that I'm corrupting, convincing you to skip school."

"Okay, okay so she wasn't happy when I told her but she didn't strictly blame you. And yeah, she's angry but she doesn't hate you. I would expect a good talking to though, my mom is good at those."

Jess wasn't sure how to feel about that, when he'd fuck up, at least in the eyes of adults around him, they were fast to drop him like a hot coal. It was a strange feeling to know that this adult wasn't going to do that to him, it was extra strange because he actually liked Lorelai and he wanted her to like him back because of who she was to Rory. On the other hand, she wasn't his mom, she was no parental figure to him at all so he wasn't fond that she thought she had a right to lecture, and possibly even punish him. He wasn't sure how to handle this situation. In the end, he decided to hold his tongue because she was his girlfriend's mother and best friend, and he didn't want her to try to break him and Rory up. So eventually he nodded his head.

"Consider me prepared. Come on, let me walk you home, it'd probably be mature and responsible of me if I talked to her about it before just not showing up tomorrow, right?" Jess suggested then wrapped an arm around her shoulder and started leading the way to the Gilmore house.

Rory made a face like she was thinking hard and put her finger to her chin, "Hmm, responsible and mature, I don't think anyone has used those words to describe Jess Mariano before, have you?"

"Ha ha ha, very funny. You think you're hilarious, don't you?"

"I have been told that once or twice before, yes."

"Well you better write down a list of those people because I'm worried about them, they might need their heads checked."

"Oh ha ha, now who's the funny one?" Rory asked with a pout which Jess didn't think twice about leaning in and kissing it away. He was happy he didn't have to fight those impulses anymore.

They walked back to the Crap Shack in companionable silence just enjoying each other's company. When they walked up the steps to her house Rory got her key from her pocket and opened the door.

"Rory, thank god you're home, come here, you have to see this!"

Rory and Jess looked at each other quickly before going into the living room which is where they heard Lorelai calling them from. They rushed because Lorelai sounded like she needed help like maybe she was even in danger. That's why they were surprised when they ran into the room and she was sitting on the couch fiddling with an alarm clock.

"Come on, sit, sit, sit. Okay, that should do it."

Rory sat down looking between her mom and the clock while Jess stayed towards the back of the room. "Do what?"

"Wait."

"What are we waiting for?" Rory asked.

"Patience, Grasshopper."

They sat there in silence for a few more moments until Rory couldn't stay quiet any longer. "Are we close?"

"Very close." Everyone in the room stared at the clock, "Hmm, getting closer."

"Should I get chips?"

Lorelai shook her head no, "Ready… and…."

The clock changed from 4:59 to 5:00 and an alarm went off, it wasn't a normal alarm, it was what sounded like pigs oinking and squealing, Lorelai looked so excited with a huge smile on her face, proud of her find.

"The clock is grunting," Rory said with her eyebrows raised in surprise.

Lorelai laughed as she turned off the alarm, "This my friend is a state-of-the-art CD clock radio that enables you to wake up to the barnyard animal of your choice."

"That is great."

"I've selected the Perky Piggies, you might choose the Cheery Chickens or the Goofy Goats."

"That is as close to a farm as I ever want to get."

"Amen, sister friend," Lorelai said as she turned to look more fully at Rory and that is when she noticed Jess for the first time. "Oh, hey Jess, didn't see you there. What do you think of our new alarm clock?"

"Jealous, really. Who wouldn't want to wake up to the sound of squealing pigs?"

"That was exactly my thought too, except without the heaping dose of sarcasm."

"Different strokes, I guess."

"Oh that reminds me, I rented Doctor Dolittle for us to watch tonight, Rory." Rory nodded her head.

"Sometimes it astounds me how your brain works. Wait, give me a second, let me see if I can figure this out." Jess put his thumb and pointer finger under his chin like he was thinking hard, "I reminded you of that TV show from the 70s with Gary Coleman, who was also in that one movie Dirty Work, and so was… what's that guy's name? Something McDonald," He paused to think but eventually snapped his finger "Norm, right that's it, Norm McDonald who's also in Dolittle." Jess was proud of himself but also a little embarrassed that he knew who was in the movie about a doctor who could talk to animals. He looked at Lorelai as if he was ready to be graded.

"Wow Jess, got it in one, I'm impressed. So what do you guys have planned for tonight?"

"Oh, I don't know, we didn't talk about it yet. But mom, Jess is here for a reason, he wants to ask you something."

All eyes turned to Jess and it made him feel awkward, he didn't like it and had the urge to say something biting and run. He always attributed that particular inclination to his father, though he never met the guy the one thing he knew for sure about him was that he ran, especially when things got hard. He took a deep breath and the feeling of needing to flee calmed.

He looked at Lorelai, "Oh, I was just wondering if I could wait to do your gutters until Sunday instead of tomorrow, there's a book fair in town that Rory wants to go to."

"Oh please, don't act like you're not just as excited about cheap books as I am." Rory chimed in. This whole situation felt awkward to her and she didn't like it so she tried to ease it. She didn't know why it was awkward now, Jess and her mom got along fine before but it was different now. Was it because she and Jess were dating now and her mom didn't like that? Or was it because of the whole New York thing? She didn't know but figured it was probably a little of both. She knew that they could get past it so that was what she decided they were going to do, she didn't want her boyfriend and her mom to not like each other, she loved hanging out with both of them and she wanted to be able to be with both at the same time without it being weird. "Hey, I got a great idea."

"What's that hon?"

"Why don't we do another movie night tonight? We don't have any plans, you've already rented the movie, Al's is having German tonight, it's fate."

"Rory…" Jess tried to interject, he liked the last movie night well enough but something about tonight felt different and honestly, he just wanted to get out of there as soon as possible. He didn't have a chance to continue his swift exit because Lorelai spoke up.

"Yeah, that sounds like a great idea, I'll call ahead and order from Al's so it's ready when I pick it up, you two run to Doose's for the rest of the snacks. Get some ice cream, it's feeling like an ice cream night for me."

"Okay, meet outside Doose's in 20," Rory replied with a nod and grabbed Jess' hand on the way out of the door. They'd been walking for a few minutes before either of them spoke again. "Sorry, I didn't mean to sign you up for movie night with my mom, I know there's a lot of other things you'd rather be doing."

Jess was just thinking up the nicest way to say 'I'm going to go home, I'll see you later' but Rory's worry and how unsure she sounded soothed him. He knew that was pretty fucked up but it was what it was, at least he wasn't the only one uncomfortable. So he squeezed her hand that he was still holding. "It's fine Rory, I'm cool as long as I get to hang out with you. Plus, your mom is cool, I just wish she wasn't mad at me." Jess was still getting used to admitting his feelings so he felt like an idiot for admitting that he was happy as long as he was with Rory but the words were already out of his mouth so it wasn't like he could take them back.

"Really? Because I, you know, feel the same. I just want to hang out with you too. And my mom isn't mad at you so you don't have to worry." Jess felt like that blatant lie didn't need a response so he just quirked his eyebrow at her and waited for her to respond. "Okay, so that was a lie, she is mad but no more mad at you than she is a me. I'm sorry, it's my fault, I feel like an idiot, I shouldn't have told her about New York. We would have gotten away with it if I didn't open my mouth but it was like when I got home I couldn't keep it from her, I don't know what's wrong with me…"

Rory had all intentions to keep talking, she was working her way up to one of her all-time best ramble sessions but it seemed like Jess knew that so he used his hand that was currently occupied with holding hers to pull her close and after her startled 'eep' from surprise, she was shut up with his lips on hers. I took no thought at all for Rory to fall into the kiss and get lost in it. When she finally pulled away she looked at him with her eyes opened wide and couldn't stop the smile when she realized he was looking at her in much the same way. It made her feel powerful, she so affected this man, who clearly had much more experience than her.

He was the first one to blink and clear his eyes of lust and contentment, "It's fine, I knew you were going to tell her."

"What do you mean?"

He shrugged, "I know what you and your mom's relationship is like, I knew she'd know within a few hours of you being home,"

"Am I really that predictable?"

He quirked his eyebrow and chuckled, "Predictable? No, I don't think anyone would be able to use that particular word to describe you. But you and your mom are more than just mother and daughter, you're friends, which is weird coming from someone whose mother barely counts as one but it works for you two."

They made it to Doosey's and Jess went to open the door but Rory pulled him back to stop him, he turned to ask her what was wrong but saw her with her hands on the window looking around while trying to be inconspicuous. "What the hell are you doing?"

"Dean, he works here."

Oh, now it made more sense, he wasn't quite sure how to feel about this but decided not to say anything. Once she decided he wasn't working and the coast was clear she breathed a sigh of relief and went to the door to enter. It wasn't until her basket was halfway full that she realized that Jess was being extra quiet. "What's wrong?"

"Nothing. I've decided to stand back and let you do your thing while shopping when it comes to movie night. I'm smarter than to try to get in the way of you and your mom's race to diabetes and an early death."

"Smart man."

They finished their shopping and exited the store just as Lorelai was crossing the street to them with three large bags from Al's. "Ready?"

"Yup, I think tonight might be the best snacks we've had during movie night ever, I think I've outdone myself."

"Such a proud moment for Mommy. Whatdya get?"

Jess tuned out most of the conversation on their trip home because he was lost in his own thoughts. Something about this whole situation made him uncomfortable and he didn't know why. This was what he'd been wanting since he came to Stars Hollow, he got the girl, stuff like that had never happened to him, he should be happy, so why was he feeling so… discontent? He'd been feeling an itch lately, not the type of itch you could scratch, it was an itch under his skin and it covered his whole body, he felt tense, always uncomfortable, like he had to leave. He thought visiting New York for the day would help, and it did, especially because Rory was with him but the itch had gradually been coming back since then and he didn't know how to make it go away. He had a feeling he had to thank his father for that particular trait, he sure had the act of running away down pat. He'd been told his whole life that he was a fuck up, that he'd never amount to anything and right now he believed it because he should be happy and content right now and he was most of the time but that feeling was still gnawing at him and he knew somehow, some way he was going to fuck up and ruin everything good that he had here. Rory shyly intertwined her fingers with his drawing himself out of his downward spiral of thoughts. He squeezed her hand softly and the itch quieted itself for the time being.

They made it back to the Crap Shack with no problems and even though it was a little awkward at first, soon they were in their what was becoming normal rhythm of movie watching and snarking. Lorelai knew she had to talk to Jess about what was and what wasn't okay to get her daughter involved in, and she would but for tonight she let herself and the kids enjoy themselves. She'd have the talk with Jess when he came over for the gutters, she promised herself that she wouldn't let herself get too angry or loud, she'd just have to get her point across another way. Jess liked to make himself seem like he didn't care about anything, especially what other people thought about him but she knew that wasn't true. Deep down he was a scared lonely kid that had been let down and abandoned way too many times in his short life. To the point where he did the letting down and kept his distance from people on his own at this point so he didn't have to get hurt or let down again. She understood that feeling better than most and she made a promise to herself when he first moved here that she wasn't going to be just another adult that hurt Jess and she planned on sticking to that promise. She'd just have to figure out the tightrope she'd have to walk to both be there for him and get her point across, it wasn't going to be easy but Lorelai Gilmore was no quitter and had no intentions of starting now.

She realized she'd been lost in thought for most of the third movie and by the time she turned back in the credits had just started rolling. She looked over to the kids ready to call it a night when she realized they'd already both fallen asleep, Rory leaning onto Jess' shoulder with his arm around her pulling her close, and resting his head atop hers. She felt both happiness and dread at the sight, she was happy because she couldn't deny the sight was adorable and they both looked happy and at peace. She felt dred because even though she liked Jess, she still had misgivings about his relationship with her daughter, he could really hurt her or he could drag her down a bad road and get her into trouble. She already knew all this but seeing them laying there like that, taking comfort from each other, it was clear to Lorelai that it was more than just attraction between the two, they cared about each other, maybe even, dare she think it, love. He wasn't planning on just dating her for a while, a kid like that, letting someone in like that, he was in it for the long haul, she knew.

She sighed, it was what it was. She'd be worried but she'd support it, support them. He just better make damn sure never to hurt her baby. She reached over to lightly shake him awake but it was like he sensed something foreign getting too close to him because as soon as her hand was about a foot away from him he jumped away with his eyes wide, looking around on alert like he was terrified and ready for a fight if need be.

No kid should ever wake up that scared. Lorelai thought. "Hey, it's okay, it's just me, the movie is over."

She saw the moment he breathed a sigh of relief and relaxed. He looked at her before moving his free hand and wiping the sleep out of his eyes then he nodded at her. Lorelai watched him for a second before starting to reach over to wake Rory up but he stopped her. "It's okay, let her sleep."

Lorelai was immediately against the idea, she'd fallen asleep on this couch a few nights in her years here, one time after too many margaritas, and a few in the same situation as this, too many movies, not enough gas to stay awake and every single time she woke up from sleeping on this couch she'd regretted it. It was a cute couch, cheap too, those two things did not equal a comfortable place to sleep. She was about to tell him no and try to wake up Rory again when Jess stood up and bent back down to pick Rory up bridal style. To say Lorelai was shocked would be an understatement but after blinking a few times to get her thoughts in order while Jess looked at her expectantly, she eventually rushed ahead to open Rory's door and over to her bed to pull back her covers. Jess followed behind and slowly put her down. In Rory's sleep during the walk over to her bedroom, she must have wrapped her arms around his chest because he had a problem getting her to let go after he was on the bed.

Jess softly brushed the hair out of Rory's face and spoke softly, "Rory, it's time to let go."

"Nuh-uh, comfy." Her daughter mumbled.

Lorelai all of a sudden got the feeling that she was intruding on a personal moment, her thoughts were solidified when Jess uncomfortably flicked his eyes over to her before responding. She decided to walk out of the room to let them have their moment, it wasn't like anything unsavory would happen when Rory was half asleep and she was standing in the next room with the door wide open. She cringed because she knew that wasn't true, she'd been the kid in that situation before and knew how much could happen in that exact situation but she trusted both of them to be smarter and more respectful than that. Her trust was proved right when Jess walked out of the room a minute later looking a little shy and uncomfortable. Lorelai decided to try to lighten the moment.

"So, you passed."

"Passed what?"

"The movie-watching test." She said as if it was the most obvious thing in the world.

"I thought I passed that last time."

"Oh you did but that was only the first interview, the second one is a surprise secret one that the interviewee doesn't know about until after the fact. Not knowing you're being graded means you'll be more honest. And you passed… so yay!"

"Uh, thanks. And I'm sorry to have to tell you this but you failed."

Lorelai gasped dramatically sounding offended, "And what, pray tell, did I fail?"

"The hostess test. There were two times throughout the night that my cup was empty, and that's not even bringing up the popcorn faux paw."

"What popcorn faux paw?" She asked faking indignance.

"You only had one flavor." He said with a shrug but Lorelai could tell he was working hard to hide a smirk. "I mean come on, no kettle corn? That's event holding 101."

She snapped her fingers as if in realization, "I knew I was forgetting something from my days at the Gilmore mansion. I'm disappointed in myself."

Jess chuckled. "So you're really okay with postponing the gutter cleaning for one day? I'm a hard worker and don't like pissing someone off who's going to give me money."

She shrugged, unbothered, "It's fine, it's been needing a good cleaning for over a year now, it can wait for one more day. I'd much rather Rory drag along someone other than me to that book fair. I hope you know what you're in for, she can peruse books for hours, I'm talking each section gets an hour for themself, at least."

"Looking forward to it," Jess said and she could tell that he meant it.

"Oh yeah, I forgot you're just as weird as she is when it comes to books," Jess responded with a shrug and that's when she noticed he kept shooting his eyes to the front door waiting for a chance to leave. "Alright, well I'll see you Sunday for the cleaners. Who am I kidding? You'll see me tomorrow morning for my next caffeine fix."

He smirked, "Yeah, I'll see you then," He said a little awkwardly before making his way to the front door.

Lorelai waited until he opened it to say anything else, "Jess, you gotta know that we're going to have to talk about your little New York adventure with my daughter, right?"

Jess' shoulders slumped a little, "Yeah, I figured."

"Okay. Well, goodnight."

"Night." He said before leaving. She stared at the front door long after he left to make his way home.

The next afternoon Jess knocked on the Gilmore girl's front door ready to pick Rory up for their… date. Even thinking the word was a little foreign to him but he spent the night getting used to the idea of being the type of guy that went on dates with his girlfriend and he was actually kind of excited for it now, and not just because of the lore of cheap books. He was relieved when it was Rory who opened the door and not Lorelai, though she didn't seem angry per se, he still wasn't looking forward to this 'talk' he was going to have to have with his girlfriend's mother.

"Hey, Jess!" Rory said with a bright smile, Jess couldn't help but think she looked beautiful in her fur-lined suede jacket and her hair pulled back in a low ponytail.

"Hey." He said taking a step closer to her. He was still figuring out this whole relationship thing but he figured it was okay to kiss her so that's exactly what he did. He smiled into the kiss when it became clear that Rory had no problem whatsoever with that type of greeting. When he pulled away it was slowly and he rested his forehead against hers, not taking his eyes away from her lips. "Ready to go?"

"Yeah, let's go." She said with a smile before grabbing his hand and leading him down the driveway and towards town.

"Someone seems excited." Jess ventured.

"Oh yeah, this book fair only happens once a year and it's where I get about 70% of my fun books for the year. You'll see, they usually have a great selection and everything is super affordable."

"Oh I know, I walked passed it while they were setting it up on the way to pick you up, I didn't think people in this town read so much."

"You'd be surprised. I'm excited to finally have someone to go with who might get as much out of it as me and who likes to read as much as I do."

Jess squeezed their interlinked hands in response and couldn't stop a small smile.