Lorelai was deciding on what takeaway to order that evening. Since Luke was staying at his apartment that night due to an early shipment in the morning, it meant that she could indulge herself in as much junk food as she wanted, without a judgemental scolding from her ridiculously health-conscious boyfriend.
She had finally settled on getting pizza when she heard a few careful knocks on her door. Did she get her dates wrong and Luke's Shipment wasn't coming in the morning? She'd been looking forward to the unadulterated pleasure of a carb coma.
"Luke! If that's you, don't think you're talking me out of my takeaway again, you haven't let me order anything for at least two weeks!"
She opened the door with a pouty face, hoping it would deter him from complaining about her eating habits. Instead she found herself face to face with a very different person than she was expecting. A face she hadn't seen in almost four years.
Jess looked at her nervously.
"Hi," he started, but she continued to stare at him.
She looked him up and down. He looked very different to the last time she'd seen him at Liz and TJ's wedding. His hair was shorter and much tidier, his clothes weren't ruffled or baggy. He was no longer so skinny and sallow in the face. His clothes fit him well, a fitted blazer, t shirt with dark jeans and he looked, dare she say, like an actual functioning adult.
He waited for her to say something, and when she didn't he nodded and started to talk rapidly.
"Look, I know I'm the last person you expected to see here, hell I bet I'm last person you want to see here, standing on your doorstep. But I came because, I thought that maybe, since it has been a few years that we could, try and maybe, bury the hatchet, you know and actually get to know one another? There's a lot of bad blood between us, but I want to try and mak-"
He wasn't able to finish his verbal diarrhoea, because Lorelai promptly slammed the door in his face.
She scoffed to herself and shook her head, folding her arms, she leaned against the door.
Who the hell does he think he? Lorelai was ready to snap at him. Why now? Why did this kid think now was the time to straighten things out with her?
"Please Lorelai" He pleaded loudly from behind her.
The nerve he had in him, to think that just because it's been years that she would what? Forgive and forget all the horrible things he had said and done, not just to her but to Rory and Luke, the two people she cared about more than anyone else in the world.
"Look, I know you think I don't deserve a second chance, and hey maybe you're right. But it's important for me-for us to get along, for Luke's sake?"
She had started to walk away from the door when the mention of Luke stopped her in her tracks. Lorelai knew that Luke was now on good terms with Jess, and even went all the way to Philadelphia to see him from time to time. She knew that Jess wasn't just important to Luke, he was family, and that meant that she needed to at least try. Luke put up with her parents almost every Friday night. She owed it to Luke to at least give his nephew a second chance.
She sighed, exasperated.
She opened the door, to find Jess's back walking towards the porch steps, his shoulders were hunched, and she could almost see the tail between his legs. He had stopped when he heard the door open and he turned around to look at her, a glint of hope in his eyes.
"For Luke?" She asked.
He nodded his head earnestly.
"For Luke," he agreed.
She stared at him a moment longer, with a curt nod of her head, she wordlessly walked into the depths of the house.
After a moment of hesitation and confusion he followed her through the door.
He followed the sound of her footsteps into the kitchen, her head was stuck inside the fridge, and he sat down at the table, taking his jacket off and placing it on the chair behind him.
Lorelai lifter her head out of the fridge with two Budweiser's in her hand, she offered him one, silently acknowledging that he was an adult and instead of stealing the beer from her fridge, she offered it to him as an equal.
He smiled at her with a muttered thanks, he took the peace offering gratefully.
"I'm ordering pizza do you want anything?" Her voice was cold, but at least she was talking.
He hesitated for a moment and then replied in a tone that matched hers.
"Whatever you're having would be great."
She glowered at him, he's the one who wanted to be here not her! He doesn't get to take that tone when he was the one who wanted to make nice.
She stomped into the hallway, and dialled the number.
"Pete! Your voice is a godsend at this hungry hour, I would like three pizzas with everything on it make it quick, or I'll wither away into nothing and then how would you be able to pay your rent?" Her voice was light and casual, a stark contrast to the mood that hung between her and Jess. She put the phone down and walked back to the kitchen.
She sat down opposite Jess and studied him.
She watched as she saw some sort of inner turmoil happening in front her, it seemed to her, that he was trying to say something, opening and closing his mouth several times, doing a great interpretation of a fish out of water. Which, she supposed, he was.
After a minute he eventually sighed and shook his head.
"You know you didn't have to buy me a whole pizza, I won't eat that much." He spoke admonishingly.
"Hah, as if you thought a whole pizza was for you. Also, what makes you think I'm paying?" her tone was mocking but light.
His lips turned up in a crooked smirk, the one that always annoyed her.
"Touché," he commended
They both drank a long sip of their beer, in accidental unison.
"Budweiser is an excellent choice in beer." It was his attempt at small talk.
"At least this time you didn't hide out on the back porch" It was a dig, but she'd tried to make it jest-full. It fell a little flat.
He had started the fish imitation again, when Lorelai heard a knock on the door, a flash of relief spread through her.
"Pete, you are such a lifesaver" she called out to her newest favourite person in stars hollow.
She gave him an almost painful grin as she yanked the pizza out of his hands, she told him to take the money out of the back of her pants, seeing as her hands were full.
He looked at her a little awkwardly.
"It's okay I got it." A voice sounded from behind her. She hadn't heard him approach, he leaned over her and handed Pete two twenties and told him to keep the change. Pete looked at Jess gratefully and promptly left.
Lorelai whipped her head back to face Jess.
"You didn't have to do that," there was an edge to her tone.
He shrugged indifferently.
"It's not a big deal."
Annoyance prickled at her edges, but she couldn't figure out why.
"No but it is a big deal, I was going to pay him." Her voice rose slightly.
Jess raised his eyebrows, it felt to her, like a challenge.
"Look, you said yourself that I shouldn't think you were paying. I intruded on your evening, it's only fair I pay for dinner." His tone was reasonable and honest.
She tried to shove down her anger, telling herself that she had to stop treating everything he does as some kind of convoluted way of one-upping her.
They sat down at the table, once again awkward silence surrounded them, only this time there was at least an excuse to be quiet, Lorelai thought. They both ate their pizza contentedly, enjoying it, each with their own vigour. Jess took his time, savouring each piece, while Lorelai raced through her two and half, almost inhaling each slice. They ended up finishing the food at the same time.
After a moment of silence, Jess coughed, he placed both his hands on his beer and started to twist it nervously.
Another beat went by and Jess sat up suddenly. He smiled at Lorelai with great effort.
"So, uh, Luke mentioned you have your own inn now that you run with Sookie," he offered to start the conversation.
She nodded, "yeah the Dragonfly Inn, along with Michel too, although I don't know if you quite had the pleasure of meeting him," she smiled down at her half-empty beer and took a long swig.
"Uh no, I didn't, but Rory told me stories about him."
The conversation came to a standstill, and both looking anywhere but at each other.
She thought, since he was really trying, that she should also.
She reached her hand over and nudged his arm in a pseudo-friendly way.
"So, what are you up to, how are things? Luke said that you worked at a publishing house and wrote a book? That's pretty impressive!"
He nodded slightly, looking down at his beer which he was still fidgeting with.
Lorelai continued.
"I mean I haven't read it but Rory told me it's really great, do you get a lot of sales on it?" she asked earnestly.
"I do okay," there was a long pause, ending the conversation.
Lorelai smiled at him awkwardly.
"We're not so good at the talky thing, you and me," she stated.
He smiled apologetically at her.
"The verbal thing comes and goes," he admitted with a wry shrug.
He downed the rest of his beer and offered her another.
"Please," she answered as she finished the last dregs of the one she was holding. Outside the sky was darkening, so she flipped the lights on in the kitchen. It was interesting to her that Jess had chosen to sit facing away from Rory's bedroom door, which was closed. She thought about that for a while, unsure of how the two of them stood. Rory hadn't spoken of Jess in a long time, and she wasn't sure if Jess asked Luke about her. She decided not to bring up Rory just yet, the conversation was awkward enough without verbalising that particular dark purple elephant in the room.
He used the bottle opener on his keys and handed one over to her, she graciously accepted and took a long drink down as he opened his own. She felt the warmth of the beer spread through her, it was nice, she hadn't sat at her kitchen table drinking beer in a long time, and definitely not with the likes of her current companion.
"Interesting place to keep a bottle opener," She remarked.
He looked down. She could see that he was really nervous, but he was still there, trying, and she felt an inkling of respect towards the boy who used to make her blood boil.
"I'm usually the designated driver actually, it just happens that the keyring I liked was ironically a bottle opener."
She just nodded. It surprised her that he took on that kind of responsibility, but didn't say anything. He swung his keys around his finger for a second before popping them back into his pocket. They both took a long swig of their beer. After a moment they both started to speak at once.
"Hey liste-"
"Look I'm-"
They both stopped and Lorelai nodded for Jess to go first.
He took a deep breath in. Lorelai saw the mental preparation cross his face.
"I just wanted to say that I was sorry for being a punk, and I'm sorry for hurting Rory. It wasn't my intention, but that's not an excuse," he looked like he might have more to say, but thought better of it.
She nodded at him grateful. It was the first time she had ever heard him apologise to anyone, and she hadn't ever expected to be on the receiving end of it.
"I'm happy to hear it. It wasn't fair what you did. But I guess I shouldn't hold it against you anymore. You were a kid. Sure, you were a jerk of a kid, but a kid nonetheless. I know I judged you harshly, but I'm protective of Rory."
He lifted his eyebrows and nodded in understanding, before he took a long sip of his beer.
"For what it's worth I'd like to think I'm no longer the Holden Caulfield you remember."
Lorelai tilted her head and assessed him for a moment, there was something different about him, he seemed a lot calmer, less angry. There was an air of inner peace about him that she would never have guessed would come from the sarcastic hoodlum who terrorised her town.
"I can see that, you're definitely more grown up."
He smiled half-heartedly, staring down at the beer in hands, his shoulders were slumped slightly.
She looked at him thoughtfully, the guy was so nervous, she really could tell. She understood how hard it was to admit mistakes. It was something she struggled with herself, maybe she had misjudged the guy after all. He had started peeling off the label of the beer. She knew that she had to do something to get him to unwind. She looked around the kitchen, searching for something that could help. Her eyes landed on a very full fifth of expensive whiskey that she had gotten from a customer at the inn as a thank you.
"Well now that we've got that out of the way." Lorelai brightened up, looking back at Jess, who jumped slightly at her voice, it seemed like she had disrupted his reverie.
He eyed her cautiously.
"Well now what?"
She smiled at him mischievously and getting up, moved over to the counter, grabbing two shot glasses and the bottle.
"Now we get to know each other!" she slammed them on the table.
He rolled his eyes at what he assumed was a joke, until he looked up at her, realisation dawned on him.
"Wait, you're serious?" he asked incredulously.
"Hell yeah, what better way to bond than getting roaringly drunk?"
Jess was hesitant, but she insisted.
"Okay fine, a few shots."
She giggled with evil glee as she sat down.
"Now I think I have to ask you the most important question of the night."
Jess visibly gulped.
"Do you want the Powerpuff girls or Charlie's Angels?" She held up the shot glasses for him to pick.
He breathed out relieved, which added to Lorelai's amusement.
He looked closely at the shot glasses and sure enough, they were themed.
"how did you managed to find a shot glass with the Powerpuff girls on it?" He asked shocked.
"I am an ebay guru" She stated proudly.
Then she pushed them more in his face doing a little impatient dance.
"Now come on! Pick your favourite feminist trio!"
He put his hand up to his chin, exaggerating his contemplation.
"Hey, Luke told me about your Drew Barrymore calendar you used to keep under your bed when you were 17, so I know you have a soft spot for my Angels" She teased him pushing the Charlie's Angels glass closer to him.
"Completely fictitious." He protested weakly, while grabbing for the glass nearest to him.
"I think I'm gonna have to go with the Angels, but only because I don't think I'd feel comfortable drinking with minors."
Lorelai chuckled giving him the glass
"If that's your story," she clunked her empty glass against his.
"Isn't there supposed to be alcohol in the glass before we cheers?"
"Hush now, I'm getting to it."
She poured out a generous amount of whiskey in each glass.
She hadn't had whiskey for a long time. She remembered back to when she was a teenager and used to steal her dad's whiskey when she went out to meet her friends. They used to play a game, that always ended in them all (especially her and Christopher) roaringly drunk. She smiled again.
"I have an idea!" She squealed in excitement.
Jess raised an eyebrow at her.
"Better than your idea to get wasted on expensive whiskey?" He asked sarcastically. She ignored it.
"Well you came here so that we could get to know each other, right?" She asked gesturing emphatically with her hand that held the shot glass, she managed not to spill a drop.
"Yes, it was…" he agreed hesitantly.
"Well I have just the way to do that!" She stated, waving the glass at him again, not spilling a drop.
"Which is…" he pressed.
"A drinking game!" Her smile was big and expressive, like she had never had an idea as brilliant in her entire life.
"So, what is this so called drinking game?" He was more eager, he already seemed more at ease, which made Lorelai relax a little in turn.
"It's called 'Shot at Truth'"
Jess shook his head.
"Never heard of it."
She dismissed him with her free hand.
"That's because I made it up as a teenager."
"Huh." He almost sounded impressed, which made Lorelai smile.
"The rules are simple. I make an assumption about you, if it's true you take a shot, and if it's not I take a shot."
He hesitated. She held up a finger for him to wait.
"But, we take turns making assumptions, so it's fair."
He considered this for a second. He took a long moment to think and then firmly nodded his head
"Okay, fair deal."
She jumped up and down with excitement, still not having spilt a drop.
"Oh, come on! there's no way you haven't spilled any of that shot, is it a trick glass or something?"
She gave him a look.
"If there's one thing I refuse to spill it is alcohol."
He raised an eyebrow, amused.
"So I see."
She sat down opposite him now, holding the full shot towards him.
"First one is free" she demanded, he nodded and they both knocked it back.
Jess winced, making Lorelai smile.
"Weak" she mocked him.
He shrugged, "evidently I'm not an experienced drinker like some."
She nodded in agreement.
"Okay, since you're the guest you can start. Go make your assumptions." She poured them each out another shot.
He took his time deciding, while she waited impatiently.
"You." He started.
She raised an eyebrow at him.
"have thought about sticking my head on a pike at least once"
She rolled her eyes.
"Lame!" she moaned as she tipped the drink back.
"Just trying to start off easy" he admitted.
"Okay fine. Hmm." She looked at him thoughtfully.
She pointed at him.
"You definitely had a James Dean phase! Admit it, you wanted to be him!" she stated accusingly.
He narrowed his eyes at her, "I may have seen a few of his movies," he replied.
"Uh huh how many times?" she asked amused.
"A couple of dozen times," he added under his breath tipping back the drink.
Lorelai was gleeful. "Hah! I knew you were channelling Jim Stark when you first moved to town," she laughed.
He stifled a laugh, forcing himself to look unamused.
Lorelai saw through it though.
Jess eyed her, a half smirk forming on his face, Lorelai gave him a mock serious look.
"Your theme song as a teenager was 'Sheena is a Punk Rocker' by the Ramones"
She opened her mouth to say something. Then glowered at him, "Punk," she threw at him playfully before taking the shot.
He chuckled at her in good humour.
She thought about a retort and a huge smile crossed her face, he raised his eyebrows at her challengingly as she jabbed him on the arm.
"Okay, how about this. You didn't want to be another brick in the wall?"
He scoffed slightly, but he downed the shot of whiskey, he was no longer wincing at every shot. It seemed to Lorelai that maybe he was starting to get a little drunk.
"Well I mean there really is no need for thought control" Lorelai remarked, smiling sincerely at him.
"Although I am against banning dark sarcasm in the classroom. I was definitely an advocate for such whimsies"
She rolled her eyes at him but chuckled, there was a long pause of silence, then simultaneously they sang out loud.
"HEY TEACHER LEAVE THOSE KIDS ALONE" which brought on a fit of giggles from Lorelai and a small chuckle from Jess. Paul Anka barked from his bed, clearly annoyed by having been woken up. Which made them laugh again. Lorelai poured them both another shot.
"To Paul Anka!" Jess cheered good naturedly and clinked their glasses together.
"Paul Anka!" Lorelai agreed.
Paul Anka barked in approval.
They were silent for a second, then Jess's face became serious.
"You regret not graduating high school."
She was quiet for a moment, surprised in the sudden change in tone. Lorelai looked at him searchingly, wondering if maybe he was projecting.
She thought about it for a while, but she just shook her head smiling.
"Not a chance, getting my job at the Independence Inn and raising Rory on my own…It was the best decision I ever made."
He looked at her, his expression unreadable, and then he gave a short nod, before he downed the shot.
She decided to go down the same path of serious questioning.
"You wish that Liz had never kicked you out of your home in New York."
His eyes widened at the question and he sat there, thinking about it for a very long time, so long that Lorelai had thought maybe he'd forgotten what he'd asked her.
"That's a complicated question, that can't be answered with a simple yes or no scenario." He sounded uncomfortable but willing to talk, which Lorelai was surprised and a little glad to hear.
She thought about it for a second.
"Okay, if we're going to get into complicated conversations, maybe we should change the rules up. How about instead of making assumptions, we ask each other questions, we either have to answer them as honestly as we can, or we take a shot. How does that sound?"
Jess contemplated the new rules, then nodded solemnly.
"Okay, so can you explain what you meant by the assumption I made being complicated?" She urged, more than a little curious.
Jess looked down at his drink, he looked like he was going to refuse and take the shot but then he looked up at her.
"It really depends on what kind of question you asked from that assumption. Were you asking me whether I wanted Liz to kick me out of my home? In which case, of course not. It sucked knowing that even your own mother didn't want to have you around." His voice was cold, verging on bitter.
She went to speak but he stopped her by continuing.
"But…I don't think that was the question you were truly asking with your assumption. What you really wanted to know, was do I regret coming to Stars Hollow."
She waited for him to continue, but he didn't.
"Well…" she urged desperately, "do you?"
He smirked at her shaking his head,
"Nuh uh, I answered your question honestly, now it's my turn."
She pouted annoyed because technically he was right.
"Fine. What's your question?"
"Do you wish that I had never come to Stars Hollow?" His question wasn't loaded, there was no malice behind his words, just simple curiosity.
It threw her off entirely. She took a long time to think about it.
Did she like the guy? No. Did she wish he had never dated her daughter? Yes. Does she wish that he hadn't hurt Luke the way he had? Yes.
But did she truly wish he'd never come to Stars Hollow?
"Honestly? I don't know." She admitted.
His face was unreadable again, and he just nodded.
"So, it's my turn to ask, okay…do you regret your relationship with Rory?" She asked, but if she was honest she would have preferred this answer from Rory, she wanted to know if her daughter ever regretted the 'Holden Caulfield' of Stars Hollow.
She eyed him, waiting for a reaction.
His jaw clenched and he went stiff.
"No." There was a darkness to the reply, that Lorelai hadn't expected.
"huh that's a-" she started but Jess interrupted her.
"Did you purposefully lead Luke on for years before you decided to give him the time of day, or were you really that oblivious?" His tone was flat, but it still managed to cut into her.
"Wow okay, that's a bit uncalled for…" her voice increased in pitch.
"Hey, you can either answer the question or drink." He gestured to her shot with a tilt of his head, he was stone faced. She couldn't understand the drastic change in his mood.
She got angry.
"Fine." She knocked back the shot just as he was pouring another one she fired back.
"Do you think you were a better boyfriend than Dean?"
He stared at her, his lips a hard line, before he tossed his own shot back.
"Do you think you would be where you are today without your parents' money." His voice was cutting, he was trying to get a rise out of her.
She gaped at him in disbelief.
"Wow, you know what? I take back my thoughts on you, you're exactly the same, but if you want the truth, fine. I don't think I would be where I am right now, but I do think I would have gotten here eventually. Maybe Rory wouldn't have been able to get into Chilton, but she still would have gone to either Harvard or Yale, regardless of my parents' money or pressure." She snapped at him bitterly, then added "Speaking of pressure Jess, did you ever pressure Rory into anything? Like sex? At a certain party the day before you left her, confused and heartbroken." She wanted him to be angry. She got what she wanted.
He narrowed his eyes at her, clenching his jaw, he grabbed his blazer from the back of the chair and stood up to leave. He knocked the shot back back.
"Fair is fair after all." He dropped the glass back on the table.
Lorelai just shook her head.
"Oh, so you're leaving again? What Jess, is it too hard? Are you gonna run away when things get too difficult for you again" her words were caustic, hoping they would sting.
He wiped a hand across his jaw, shaking his head incredulously, before he smiled a humourless smile at her.
"You don't get it, Lorelai, you fit into this place so perfectly. I never did, it became too much, the whole goddamn place was suffocating me, and everyone wanted me out…and Rory…God Rory was the only person who ever believed me, her and Luke both. Yeah, I let them down, the only people who really truly believed in me and I failed them. I just wanted to make them happy, I wanted to do what was right, and the only thing I could think to do was leave. I messed them up, and I knew that they would be better off without me, so yeah, I screwed up, and that night at the party I was so messed up. I found out that I wasn't graduating and that Luke, the only family member who actually gave a damn about me, was gonna kick me to the curb. Hell, I deserved it, I was a fuck up, and I couldn't even take Rory to the prom, the one thing that I could do that would make her happy, and I wasn't able to. Just like every other damn thing. Do I think I was a better boyfriend than Dean? No, but Jesus fucking Christ you all were so keen to tell me how terrible I was in comparison. I tried Lorelai. I fucking tried. I was never used to having someone care about me. So, when that party came around I just wanted to make her happy, I wanted her to feel happy with me, I wanted to show her how much she meant to me, I went too far I admit it, but fucking hell, I would never pressure her, I would never do that to Rory because…I am in," He stumbled over the last part of those words and quickly tried to reiterate them. "Was, I was in love with her," he tried correcting himself. His hand flew up to his temple, it looked like the drink had finally hit him all at once, he stumbled slightly, before trying to correct his balance, he rested his hand on the back of the chair for support.
It didn't matter, she'd heard it, she knew it wasn't a mistake, but his lips loosening from the whiskey. Lorelai looked at him in shock. It was the most words he had ever said to her over the years, and it came out all at once. There was so much hurt and pain on his face, so much regret. He looked at her like a scared little kid. Her eyes softened and she started to talk.
"Jess I didn't know, I-"
He threw his hand up in dismissal.
"No, doesssn't matter thisss, uhhh was, this was a stupid idea." The words were becoming slurred the more he tried to talk, it seemed like he was having difficulty trying to put together a coherent sentence. "God my head is spinning, we, we shouldn't have done this." His words were stumbling out of his mouth at this point, he wiped his hand over his face, widening his eyes trying to see through the blur of alcohol.
For the first time ever, she saw him for exactly what he was, what he had always been. A sad, confused and neglected kid. It pulled at her chest, she felt herself soften, she had no idea quite how messed up this kid really was.
There was an audible silence in the air, and Jess turned toward the back door, but Lorelai caught his arm, stopping him.
"Jess. This wasn't a stupid idea. I actually think it was what we needed. From the pop culture quips to the harsh words. I think this is a start." She paused for a moment, "I think, we have both had too much to drink, and that we should both get some rest, and talk some more in the morning."
He sighed, but nodded with a sad smile.
"I guessss I should be, uh, I should be going then, look I'm reeeeally s-sorry. I shouldn't have said what I did, it seemsss I still have that ssshitty built-in defence mechanism." He offered her, he seemed to really be struggling with words at this point.
"Once a punk always a punk right?" She smiled at him sweetly.
"Thanks Lorelai, I'm glad...I'm glad we did this" He went to shake her hand, but she pulled him in for a hug. What can she say? Tipsy Lorelai was a hugger.
He received it awkwardly, but not insincerely.
He smiled at her, before he turned to go again.
"Hey, where do you think you're going?" She asked accusingly.
"Umm, home?" He asked confused.
"No, you are not, you are in no state to drive, it's too late to get a bus and you'll freeze to death if you sleep outside this time of year."
"I was actually gonna go to the diner" he started but she just pushed him towards Rory's room.
He hesitated, but she was stronger than she looked, and he was unsteady on his feet as it was.
"Okay, I guesss I should s-stay, again I'm sorry" he started again.
She shook her head. "Don't worry about it. We'll talk tomorrow. Good night."
With the last little nudge he opened Rory's door and cautiously turned to go inside.
Before he got past the threshold of Rory's door he turned, leaning completely on the doorframe.
He looked at her through squinted eyes, "h-how are you not drunk?"
Lorelai laughed, "Years on years of experience, you're still in training young padwan"
He smiled a sloppy smile before turning back into the room.
Lorelai watched him as he closed the door behind, a small smile played on her lips, this was not at all how she had planned to spend her Luke-free night.
