Chapter Text
October 2009
"I don't understand why dinners with Paris needs a dress code," Jess half-complained as the two entered their apartment. As he worked on undoing his tie, Rory locked the door behind them, smirking. "I mean, does she think we don't know how to dress ourselves? Did she really need to laminate it?"
"Well, what if you spilled something on your copy? Lamination is a much better option than having to ask Paris for another one," Rory retorted as she pulled off her heels, her feet aching more than usual that night.
Dinners with Paris and Doyle were just part of their routine. The two had been dating for several years now. After Luke had invited Jess to Rory's Bon Voyage party, the two had caught up and been practically inseparable ever since, even surviving long-distance while Rory covered the Obama campaign. So, when the campaign ended and Rory had landed an internship with The New York Times—the very one she'd been rejected from a year prior, apparently the campaign had greatly added to her resume—she'd settled in New York. Jess, who just so happened to have room available (he'd moved to New York following Truncheon's relocation), had offered her a place to stay. Eagerly, she'd accepted, and the two had been living together ever since.
"Why did Paris drag you to the bathroom after dinner?" he asked as he pulled off his worn Converse.
Unsurprisingly, Rory had yet to shake Paris. Paris and Doyle had gotten married shortly after college, with Rory serving as her maid of honor. Shortly after, the two had their first child, Noah. Now, Paris was attending medical school and expecting another baby, or at least that's what she'd told Rory when she'd cornered her in the bathroom of the restaurant during dinner.
"She's pregnant again," Rory answered. "She wanted my thoughts on her very detailed, updated life plan, including which preschools she should be aiming for if she wants her kids to get into Ivy League colleges. She's aiming for Yale, but would also settle for Princeton."
Jess couldn't help but laugh as the words rolled over him. "Already?" he asked sarcastically; however, Paris planned her life so meticulously that this didn't surprise him. Having lacked the whole two loving parents aspect in her own upbringing, Paris was eager to have it for herself.
Rory nodded. "I mean, you can't be surprised. After all, it was in her five year plan."
"I guess," Jess relented, flinging his coat over the back of their couch.
"How was work?" Rory asked gently as she made her way to the kitchen, placing her leftovers in the fridge. When he didn't reply, she turned to face Jess, seeing the same defeated expression that would settle on his face the past few months whenever Truncheon was brought up. "Hm?"
Ever since their relocation and the recession, Truncheon had been shaky. As an independent publishing press, funds were running increasingly low and investors were scarce. To try and help combat this, Jess had increasingly been working more hours for less pay. It was safe to say that he was the most stressed and overworked as Rory had ever seen him.
Jess noticed her eyes on him and shrugged, struggling to be nonchalant. "Fine," he said, trying to deflect, although they could both tell it was a lie. He tried to avoid the topic with Rory—it made things easier, at least for him. Every night he'd get to come home and try to pretend that everything was fine, that his life's work wasn't crumbling into pieces around him.
"I'm going to go get out of these clothes," Rory said suddenly, sensing the obvious tension in the room (and, in all fairness, her evening dress wasn't the most comfortable). "Make me some coffee?" she added.
"Two cups this morning, several more at work, I'm sure, two at dinner...when will the addiction end?" Jess teased, although he was grateful for the subject change. His eyes lingered on her as she made her way down the hall of their apartment. Part of him wanted to confide in her, he really did. But how could he? Here he was, failing at the only thing he'd ever truly been passionate about, the only venture he'd ever taken seriously.
Thankfully, a distraction arrived—the flashing light of their answering machine suddenly caught his attention. His brow furrowed at this, fearing it was something work-related. Since he refused to buy a cell phone, his co-workers often resorted to calling their home phone if they wanted to reach him after hours. Reluctantly, he allowed the message to play as the coffee brewed. However, the message was not from Chris or Matt or any of his other co-workers. It was from none other than Lorelai Gilmore, a frequent message-leaver on their answering machine. Although Lorelai hadn't been Jess's biggest fan in the past, she tried to remain supportive of their relationship for Rory's sake. In fact, he was beginning to think that her mere tolerance of him was turning into mild acceptance.
"Hey kid, it's me. I just got your message—wow, that is incredible news! My daughter, the Managing News Editor of The New York Times! Not that I'm surprised, of course. But, wow, that is something. When you're here this weekend we'll have to do something to celebrate. I'm thinking fireworks, petting zoo, Founder's Day punch, a parade in your honor. Kidding, kidding! But definitely something near that level, just something that won't get me on Taylor's bad side. This is so great, kid, I'm so proud of you. I bet you're out celebrating right now, so call me back when you get a chance. Love you."
Jess paused as Lorelai's words rolled over him. Her message was long and rambling, per usual, but that was unsurprising. What was surprising was the content of the message. Managing News Editor of The New York Times—Rory's dream job which was, apparently, a reality for her now, something he knew absolutely nothing about. He knew they'd been hiring and that she'd interviewed, but the extent of his knowledge ended there. Besides, she'd made it very clear to him that she wasn't getting her hopes up, that she'd applied on a whim—after all, she was just an assistant, a fact checker, someone who got coffees, that's what she'd told him. This was huge, and he knew nothing about it.
"Coffee ready?" Rory asked, suddenly snapping Jess back to reality. When he turned towards her, he could tell that his shock was written all over his face. "Are you okay?" she asked, tone gentler than before.
"You're...you got the job?" he asked, the words tangled in his throat.
Rory briefly opened her mouth, only to quickly shut it again, unsure of what to say. The feeling was unwelcome and unnatural to her. Finally, she settled on something, figuring that anything was better than silence. "How'd you...?" she started, her mouth giving up, betraying her.
Jess gestured towards their phone. "Your mom. She, uh, left you a message."
"Oh," Rory breathed, everything finally registering. She bit her lip, trying to figure out the best way to explain this all to Jess, to untangle it in her mind. "I...I just found out, I swear. They called me this morning," she promised, practically pleading. "I was about to tell you, Jess. I meant to, really. I did."
He nodded, although it was insincere. "Why didn't you?"
Rory sighed. "I don't know," she replied, which wasn't true. She knew exactly why, they both did. It didn't need saying. However, she said it anyway. "I don't know. I just...I thought with Truncheon and everything..."
"What do you mean?" Jess asked suddenly, the words sharper than he'd meant them. However, he didn't take them back, he stood his ground, waiting for Rory's response.
"I didn't want to rub it in your face," she admitted. He stared at her, waiting for her to continue. "I mean, I didn't want to flaunt it."
Even though he already knew the truth, it was like a slap across the face for Jess. That was how Rory saw him? As some whiny, unsupportive boyfriend who would fall apart at any mention of her success? Jess knew this assumption was unfair, he really did. She was just trying to be protective, gentle, even...something he wasn't used to. He didn't enjoy the feeling.
"You really think my ego is that fragile?" he demanded, defensively crossing his arms against his chest. "That I wouldn't be happy for you?"
Rory's expression softened at this, which was not a reaction Jess had been expecting. Anger, that he could handle. Disappointment he was used to. But this? This was foreign to him. "No, it's not that..." her voice trailed off, unsure of what to say.
"Then what is it? You feel sorry for me?" Jess continued, unable to stop. He didn't want to fight, really. He knew that she meant well but, for some unknown reason, he couldn't stop himself. He didn't know when to quit. "Because I don't need your pity."
"I wasn't offering any," Rory shot back, suddenly irritated by this assumption. This Jess was more accustomed to, this he could take.
"You don't need to walk on egg shells around me, I get it—you're special and I'm not," he continued, jaw clenched. "Believe me, your family reminds me of that fact more than enough."
For a second, Rory wanted nothing more than to comfort Jess. However, by the defensive tone to his voice, she could tell that wasn't what he was looking for.
"Is that what this is about?" Rory continued, eyebrows furrowed as she attempted to read Jess's expression, a task easier said than done. "You're acting like this because you don't want to come home with me for Thanksgiving?"
"No, I—" Jess started, before realizing he, himself, wasn't sure why he was having this reaction. Suddenly, all he could focus on was the intense feeling of Rory's gaze on him, practically burning him alive. "I get it, you're successful. It's probably a little easier when you have an Ivy League education and a trust fund all set up for you."
This signaled a change. Like most couples, Jess and Rory fought sometimes. The two would bicker over what movie to watch or what to eat for dinner, occasionally argue about who has to do what chore, and childishly mock one another over stupid things, but prior disagreements were always superficial. Nothing like this, never cruel.
Anger flashed through Rory's face. Jess had touched a nerve and they both knew it. "You're kidding me, right?" she exclaimed, almost laughing. "You could've gone to college, Jess, no one was stopping you. And I don't touch that trust fund, you know that."
"Doesn't mean it isn't there," he shot back, almost amused by her naivety. "Must be nice to have grandpa and grandma's safety net to catch me if something goes wrong."
The divide was always there. Although growing up in a shed for the first years of her life was far from materialistic, what Rory had lacked in money in her childhood was made up for in love and care. Jess, on the other hand, had been on his own ever since Liz had deemed he could fend for himself.
Rory shook her head, continuing in wake of his silence. "I know things with Truncheon are shaky right now, but it's not because of you. Matt told me you guys got rejected from getting a business loan, but most businesses would right now, I'm sure—"
"Matt told you that?" he interrupted, face growing red. Asking for a loan had been their final straw, and Jess had felt so defeated when they got rejected he couldn't bring himself to tell Rory. He hadn't even told her they'd applied for one. "When did you talk to him?"
"He called looking for you a couple nights ago when you were asleep and I asked how things were," Rory responded. "I mean, I wouldn't have to hear this from him if you'd just talk to me."
"I—he had no right telling you that," Jess said.
Rory shook her head. "This isn't about him. I'm worried about you, Jess. Why can't you just talk to me?"
"Don't worry about me," he deflected. "Or Truncheon. It's my business, I'll figure it out."
"That doesn't mean I can't help. I'm your girlfriend, I want to hear about your life, the good and the bad," she pressed. "Truncheon will be fine, okay? There are other options, you'll bounce back. The economy is just bad right now, but it won't be forever."
Jess couldn't take it any longer. He didn't want to sit there while Rory reassured him, he knew he didn't deserve it. He'd allowed his fear to manipulate him into getting in a petty fight. He couldn't take Rory's rambling, her belief that the two of them were the same. There weren't 'other options' for them, none of them had familial wealth to fall back on or good credit scores to get loan approvals. They were screwed.
"I need some air," he said finally, head pounding. Rory watched as he grabbed his jacket from the couch, shoving his wallet in his back pocket.
Her eyes following him as he made his way to the door. "Where are you going?" He didn't reply. Instead, he reached towards the door knob. "You can't just leave like that. Jess."
No response.
"Are we still going to Stars Hollow?" Rory asked weakly, fearing the answer. Thanksgiving was rapidly approaching, and Lorelai was very eagerly expecting her daughter home the next day.
He paused. "I'll be right back," he murmured, although he still couldn't bring himself to turn and face her, to see the defeated look on her face, knowing he'd caused it. He hesitated for a moment but, ultimately, opened the door, leaving swiftly.
After the door closed Rory wavered for a few seconds, eyes fixated on the door as if she could will him to come back. She gave up a few minutes in, resigning herself to bed. She just needed a good night's sleep—that was all. They both did. Then everything would be back to normal...right?