May 2006

Ever since Liz's wedding, Jess and Luke made it a point to check in with each other, mainly when there was a noteworthy event to discuss or when it felt like too much time had passed. So a few weeks after Luke visited Truncheon and Jess found out he would be meeting some publishers in Stamford, it felt like the right time to pay a visit to Stars Hollow and spend a few nights in town.

The "CLOSED" sign was flipped and Luke was stacking chairs onto tables as the bells sounded and Jess opened the door.

Luke turned towards him, hands still holding the legs of a chair. "Jess! Did I forget you were coming?"

"No." Jess made his way in, pulled a chair off of a table by the window and sat down. "I probably should've called. I have a meeting down in Stamford. Thought maybe you wouldn't mind if I stayed a few days?"

"Place is all yours." The upstairs apartment was empty most of the time now that Luke and Lorelai decided to expand her house.

"Cool." Luke joined him and sat at the table as a moment of silence fell between them, but Jess could see Luke was on the verge of saying something he probably didn't want to hear. "What is it Lassie?"

"Oh it's nothing, never mind." Luke leaned forward and folded his hands in front of him. "Well -"

"And there it is." Jess rolled his eyes and fell back in the chair.

"It's just that the last time I saw you, in Philadelphia, Rory was there, and usually I'm not surprised to see Rory, since I'm marrying her mom, but I wouldn't expect to see her, in Philadelphia, with you, in Phila-"

"I invited her. She showed up." Jess cut him off before he could use the words 'Rory' and 'Philadelphia' again.

"So, you're friends now?" Luke unfolded his hands using them to gesture in unison with his words.

"I would use that term very loosely." Jess got up, walked behind the counter, and started brewing a pot of coffee as Luke turned in his chair to face his direction.

"What the hell does that mean?"

"Nothing." Jess focused on the coffee as he spoke.

"Nothing?"

Jess looked over his shoulder. "Yes. Nothing."

"Ok then." Luke threw his hands up in defeat and sat back as Jess poured himself a cup then turned to face him again.

"And - maybe I kissed her."

"You kissed her?" Luke was sitting forward now, forearms leaning on his thighs, wide eyed, face filled with disbelief.

"It's not a big deal."

"Not a big deal?"

"Do you have to repeat everything I say in the form of a question?" Jess walked back to the table and sat across from Luke, enveloping the coffee mug in his hands.

"But Rory has a boyfriend."

"That minor detail wasn't shared with me."

"But you saw her in November with Logan."

"You mean Prince William?"

"Jess-"

"She showed up alone. To Philadelphia." He shuffled in his seat. "Plus, I asked her if she was with him and she pretty much lied to me."

"Why would she do that?" Jess looked down at his coffee, then back up at Luke. He wasn't sure if he wanted to go there. Partially embarrassed with himself. Partially embarrassed for her. But he had been suffocating and talking to Luke did give him some catharsis.

"I told you what happened when I saw her in the fall." Luke waited for him to continue, but he didn't, so he leaned slightly forward over the table, head dipping down, eyes and hands gesturing for him to go on. "Look, I thought she fixed the situation. She said she fixed the situation and I guess my interpretation skills weren't at peak that day."

"So you kissed her?"

"We were just sitting there, alone, and she gave me that look. You know. That look." He pointed his finger out in front of him. "Forget it. You don't understand" Jess slumped back into his chair.

"No, no. I get it. She gave you a look." Luke sighed. "And I take it, it didn't end well?"

"Gee, how'd you crack that code?" Jess mocked and turned his head sideways as his eyes went wide, but then he took a deep breath and ran his hand through his hair, looking down at his coffee mug as he spoke again. "She told me she's in love with him."

"Wow."

"Yep." Luke was staring at him with concern. "Don't worry. I'm a big boy, I can handle it."

"Look, I may not understand this whole thing with Rory. With the weird, back, and forth, and complete lack of communication, but I know you care about her."

"I do not ca-"

"I know you still care about her." Luke said it again.

"Got another self help book back there?" Luke rolled his eyes to the top of his eyelids as a breath came out of his flaring nostrils.

"I know you're not the guy, that pines for the girl, for his entire life -"

"I'm not pining." Luke lifted his eyebrows as if to say come on, really? "I'm not. I don't pine. I thought maybe the timing was right. She was there. I was there. That's it. No more, no less. She doesn't want me? That's fine. I'll move on."

"Sounds easy."

"Yea." Jess nodded.

"Hey, I understand better than anyone. Me, remember? The golden retriever with a nice leash." Luke offered the words in jest, but reminded them both of a time he berated Luke for being in the same position he found himself in now.

"Alright, I get it, ok? You waited around for eight years and it worked out for you." Jess was fiddling with the mug handle. "But I'm not you."

"You're more like me than you'll ever admit."

"Geez, God help me."

November 2007

He knew he needed to get used to the whole seeing her thing. Luke and Lorelai were back together, and given how well things were going, it was expected Rory would be in his life indefinitely. So when Thanksgiving came around and Luke invited him up to Stars Hollow for dinner, Jess agreed, knowing he couldn't put off the awkward, but inevitable reunion forever. And maybe it was best to get it out of the way now, while Luke and Lorelai were around to buffer the conversation and prevent him from being left alone with Rory for too long.

He didn't expect to be so nervous, but upon arriving at the Gilmore's front door, he is abundantly aware of how his heartbeat picks up and his hands feel unusually clammy for a late November day. It's been four years since he's been face to face with this door, a year and half since he last saw her, and he's bracing for what is waiting on the other side, but before he has enough time to drown in his own thoughts, Luke opens the door to greet and invite him in.

Seeing her ends up being a lot easier than he thought it would be. She's sitting at the kitchen table, sandwiched between Sookie and her mom, caught in conversation, and he can't help but admire how fucking beautiful she still is. Her eyes are more blue and captivating, if that's even possible, and she grew her bangs out just enough to part it off to the side as the rest of her hair falls past her shoulders. When their eyes finally meet, he gives a straight mouthed smile and nods his head in acknowledgement of her. She's nervous too and he knows. Her eyes are flickering and she keeps playing with her long sleeves, pulling one side past her wrists, then focusing on the other side to do the same.

But dinner comes and goes quickly and he knows it was Luke that made sure to keep Rory at least a few seats away which he's grateful for. He's also grateful that Sookie and Jackson take over the conversation, both holding strong on their positions of best way to cook a Thanksgiving turkey. And before he knows it, Sookie, Jackson, and their kids have left, Luke's kitchen clean up is nearing an end, Lorelai has passed out upstairs blaming her tiredness on the turkey, and Rory is half asleep on the couch in the living room watching The Twilight Zone.

"Convenient that Lorelai decided to be 'tired' right around clean up time." Jess finishes his air quotes taunting Luke who is putting the final leftovers into the fridge.

"Just as convenient as you. He who suddenly has an interest in football."

"Hey, I'm a guest!" Jess throws up his hands in defense before taking another swig of his beer.

"I'm glad you came. I know it's been a while and I wasn't sure how you'd feel about coming up here, but it means a lot... you coming up here-"

"Seemed important enough for you to leave me a rambling 5 minute voicemail." Luke smirks as Jess stands and grabs his coat off the back of his chair.

"Where do you think you're going?"

"See I don't live here -" Jess is straightening his coat collar as Luke's face settles and becomes more serious.

"Nope, you've been drinking. Walk it off. You can stay at the diner tonight."

"Oh come on! I had a few beers." He knows Luke isn't going to let up and honestly, he's dizzier than he initially thought and had his fair share of beer... and several glasses of scotch. So he doesn't push on it anymore and throws Luke his car keys. "I'll see you tomorrow."

He heads out the front door and he's craving a cigarette. Bad. He's managed to quit, but saves them for occasions when he drinks, which are far and infrequent, but he needs the familiar drags right now, so he pulls the pack out of his inside coat and puts the cigarette to his mouth, ready to light it up.

"Luke is going to kill you." He jumps back, startled, and the cigarette falls to the ground.

"Geez!" He turns his head over his shoulder and there she is, Rory, sitting on the patio loveseat, wrapped in a blanket. This is the moment he's tried to avoid all night and he yells at himself in his head for not checking her whereabouts before venturing outside, but he is drunk after all.

"Sorry, didn't mean to scare you." Her voice is soft and gentle and he can hear a little bit of a slur. "Heading home?"

"Actually staying the night - at the diner. I had a few drinks and Luke is feeling very paternal tonight."

"That's probably wise." He nods in agreement as he plays with the lighter in his hand. "Do you want to sit with me?"

He takes a deep breath, looks out towards the escape route of the front yard, and decides against it. "Ok." He turns on his heel to take the seat next to her and she stretches the blanket over his lap, making sure they're both covered, which takes him by surprise.

"I'm so full." She slumps into the seat further.

"I've seen you eat before." He points his thumb behind him. "That back there was nothing."

"This is true." She nods with a small smile. "I'm a little drunk actually."

"Really?" She reaches next to her and picks up a bottle of wine which he reads out loud with a grin. "Sweet Bitch Rosé. Very classy. And will definitely leave you with your head in the toilet tonight."

"Hey! I like it. It's candy and dessert and alcohol all in one!"

"My mistake." He's drunk and suddenly very aware of how close she is next to him, sharing a blanket, their shoulders practically touching.

"So what's new in your world?"

"Still in Philly. Not sleeping out on the street yet, so I'd say all in all, going well."

"That's good." She moves her bangs back in place and he's thinking about how beautiful she is again and how maybe this would be a lot easier if she weren't so beautiful because he's starting to get lost in her eyes and it's too easy to fall back into this rhythm with her. "You were right."

"Of course I was." He smiles and nudges her shoulder with his. "What exactly am I right about this time?"

" ." She takes a sip of wine and inhales a deep breath before turning her eyes to his. "It is too rough for me."

"What is?" She doesn't answer, just shrugs her shoulder in disappointment and defeat. "Journalism?"

"I don't think I can do it." She sounds so small and broken and lost again. "I don't even have bombs going off behind me and I can't do it."

"You can do it, if it's what you want. I promised you that."

"I don't think it's what I want." He knows she's on the verge of tears and sugary wine is not helping. "I spent 22 years of my life trying to be Christiane Amanpour, and now that I'm on the road to doing it, it's not what I want. And what if it takes another 22 years to figure it out!"

"Ok I think it's time to put the wine down." He grabs the bottle from her hands and settles it beside him on the ground. "You can do whatever you want. You love to write. You just gotta figure out what that means for you. There's no shame if this isn't what you want. Maybe being on the road isn't for you."

She knows he gets it. Knows she is a creature of routines and lists. Someone who needs stability and wants to be able to know what's ahead of her, or at least if the path is unclear, has a place she can call home to figure it out.

"Thanks." She's playing with the stitching of the blanket now. "You're like my own fairy godmother."

"Well bippity-boppity-boo." She giggles softly and her smile is so radiating he can't help to turn his lips up slightly and lean back in the seat staring ahead as the quiet of the night surrounds them.

"Jess?"

"Yea?" He shifts his gaze to her eyes.

"I'm really glad you came today." She pauses before speaking again. " And I'm so sorry about what happened the last time I saw you."

"Rory-" He doesn't want to rehash old wounds. The first time was painful enough. Hearing her admit she was in love and it wasn't with him, those were daggers, but eventually he was able to get through it, although maybe not ever over it.

"I am. I'm so sorry. That's not the person I want you to think I am."

"I know it's not." He assures her, but she's still feeling guilty and she won't look at him.

"I'm not with that guy anymore."

"I'm sorry." And he is, though relieved, not because he likes the guy, but because he knew she loved him enough to put herself through whatever pain he caused her.

"Don't be. I'm the one who ended it. He proposed after graduation and I said no."

"Oh."

"I wasn't as sure about how much I loved him when I had to consider forever. About what I would be giving up." She takes another deep breath and though this topic isn't at the top of Jess' list, he doesn't stop her, even if he knows it could end up hurting him. "It kinda felt like I was with him because it looked like the perfect picture. It was exactly what everyone else wanted, it's what my grandparents wanted… but I wasn't myself with him. He didn't inspire me. I kinda just faded into the backdrop."

"I guess that makes sense." Jess finally gets it. Understands how she could fall in love with a guy like him and stay by his side.

"Sorry, I'm drunk and clearly cannot stop talking. I'll be shutting up now."

"I don't mind." He tries to assure her again and this time she believes him because she's looking into his eyes.

"You were right about something else too."

"Yea?"

"I think you do know me better than anyone. I wouldn't have gone back to Yale if it weren't for you, you inspired me. "

His heart sinks deep into his chest, he knows what those words really mean. So he nods with a smile and lets the silence take over until they're both just sitting and staring into the night, the sound of wind and crickets the only noises to be heard. And it's in this moment he knows that what he feels for her is never going away.

His eyes are staring into his lap, fingers fiddling aimlessly while she looks out in front of her, blue eyes glazed from alcohol and twinkling in the starlight.

"Rory?"

"Yeah?"

"I still - I'm- I'm pretty sure I'll always -." He doesn't need to finish and she doesn't let him. He can't look at her, eyes still focused down on his lap, breath deflating from his lungs and catching in his throat. He's not sure if it's the right moment, but he's drunk and brave and he can't help himself from trying to say the words he's been burying for way too long.

"I know." The sound is barely audible, but is gentle and understanding because his words don't surprise her as much as she thought they would, because she's always known. She takes a deep breath and shifts her gaze from the sky over to his face which is still looking down.

"I'm sorry, I didn't mean to get all Gatsby on you. To be fair, I think I drank my weight in scotch tonight."

She reaches over to lay her hand on top of his, interlocking their fingers as his eyes move to hers in surprise from the touch.

"Jess… me too."

She inches closer to him and rests her head in the crook of his neck, looking down, fingers still locked together in his, as his free arm wraps around her shoulder, pulling her in closer. He wants to jump out of his skin, wonders if he is dreaming, but he doesn't want to ruin it. He leaves a soft kiss on the top of her head and he's certain she can hear and feel his heart beating in the still of the night. And they stay like this for a while. His chin resting on top of her head, arm wrapped around her shoulder, pulling her in as close to him as possible as she draws circles in his hand with her thumb.

He wonders who will move first when suddenly Rory pulls back and looks into his eyes, her free hand moving to his face, fingertips on his neck, just below his ear, and her thumb tracing his jawline. She's dizzy from the alcohol, brave, and confident as she moves her hand from his face to the back of his neck, tangling her fingers in his hair. He hasn't moved, hasn't shifted his eyes from hers. She leans in slowly, angling her head slightly as she presses her lips against his, the familiar feeling of electricity pulsing through her as he lifts his hand to cup her face, both of their mouths opening for just a bit more of each other. She finally pulls away and leans her forehead against his.

"I know I don't have it all figured it out right now, but I know this-you-" He doesn't let her finish.

"It's nice to finally know." He presses his lips against hers, softer this time, then moves them to her forehead and whispers against her skin. "You'll figure it out, I promise you will."

They never speak of that night again. Of that moment that was meant to be frozen in time and left on the patio. They don't try to figure out what it means to their new and currently incompatible lives. They don't need to. They both know this isn't the right time to talk about an "us". And they both accept in unspoken words that when it comes to each other, whatever this thing is they were lucky enough to find as teenagers, is never really over.