Luke's words ran through Jess' mind as he sat upstairs in the diner apartment that night after the wedding. He knew that nothing would make him happier than loving Rory and having her love him back. He just didn't think he could survive having his heart broken again if she didn't feel the same way. He thought of all the times he'd put himself out there for Rory before. When she ran away from him that night at the Firelight Festival he knew he'd never forgive himself if he didn't tell her how he felt so he told her that he loved her, but then like an idiot he got in his car and drove away. That was his fault he knew, but then he came back a few months later for Liz's wedding. He worked up his nerve and went to see Rory at her dorm. Jess pleaded with her to leave with him. He told her he hadn't been ready before, but he was now. Still she hadn't believed him. Jess really thought that some part of Rory still wanted to be with him, but she said she didn't and it had crushed him.
Jess couldn't blame Rory for not leaving with him that night at Yale either. He must have looked like a crazy person barging in like that begging her to drop everything and run away with him. Even though he told her he was ready, looking back he realized that he wasn't. He still had a lot of growing up to do. He did a lot of self-examination over the next year and a half as he wrote his book, the whole time thinking of Rory. He couldn't wait to show her his book when he finished it. He didn't know exactly what was going on with Rory, but he could tell something was off. It took some coaxing, but he finally got it out of Luke that she was staying with her grandparents in Hartford. The night he walked up outside her grandparents' house and saw her standing in the driveway she seemed genuinely happy to see him. He couldn't help himself when he quipped about his new job as a professional driveway stalker. She didn't miss a beat and asked him if it paid good. It felt good to joke like that with Rory again. When Rory told him he looked good he figured she was just saying that to be nice. Though when he returned the compliment he definitely meant it.
Once they were inside Rory admitted that she was a little nervous and he told her that he was too. Jess really thought now might finally be their chance. He loved the way Rory's face lit up when he showed her his book. He still remembered the exact cadence of her voice when she kept repeating "You wrote a book? You wrote a book?! You wrote a book." At the time Jess still couldn't quite believe it himself. She seemed so excited to find out what stores stocked his book so she could see it with her own eyes. He couldn't help but grin from ear to ear when Rory told him her plan to write a recommendation for his book and place it in the Staff Recommendations section. He felt his heart might burst when she bragged on him and told him she always knew he could do something like this. He wanted to kiss her right then, but he resisted the urge. Jess told Rory he couldn't have done it without her and he truly meant it, she was his muse and the one person who had always believed in him the most.
Jess really wanted to tell her how he felt about her, but that night in her grandparents' house just didn't feel right. He asked if he could see her again and they made plans to go to dinner the following night. Jess wanted to tell her that his feelings for her had never waned, but then Logan had showed up. Things only went south from there. Jess despised Logan's pompous attitude as he offered to pay for dinner. Logan wore his jealousy on his sleeve like a schoolboy when he questioned whether Jess and Rory used to date. Jess could tell he had gotten under Logan's skin when Logan questioned him about his novel and Jess just couldn't help himself when he said "You seem very obsessed with length." "I'm just trying to get a picture in my head that's all." had been Logan's reply. They had gotten into a literal pissing contest and Rory tried to feign ignorance and play peacekeeper. Jess knew Rory was far too intelligent to not see right through their innuendo. He stopped pushing it though because he didn't want to make her uncomfortable.
The night ended with Jess storming out and yelling at Rory for dropping out of Yale. He didn't know what had happened to the Rory he once knew and he refused to sit idly by and watch her torpedo her hopes and dreams. He wasn't trying to be harsh, but he so vehemently despised seeing Rory so aimlessly adrift that his tone came out much harsher than he intended. Jess felt horrible for raising his voice to Rory so in a last ditch effort to make up for it he just said that maybe they'd catch up at a better time and halfheartedly wished her a belated happy birthday. Her face looked so crestfallen that it nearly tore his heart out, but the damage was already done. Jess walked away with that image of Rory burned in his brain.
Jess remembered how everything went down the last time he put himself out there for Rory. He was thrilled when he saw that Rory had come to Philadelphia for the Truncheon open house. He found himself looking for her across the room so many times that night, anxious for when he would get his chance to talk to her alone. When it was just the two of them later he congratulated her on becoming editor of the Yale Daily News. All seemed right again, like everything was fixed and Rory said it was. Next thing Jess knew he was leaning in to kiss her, he couldn't help himself, he was drawn to her like a magnet. At first Rory kissed him back, but then she stood up and started rattling on about how she shouldn't have come and it wasn't fair to him. It felt oddly similar to the first time she'd kissed him the day of Sookie's wedding.
Jess felt like his head was spinning. He was so confused, but then it all became painfully clear when Rory said "I couldn't even cheat on him the way he cheated on me." It was in that moment that Jess realized Rory was still with that guy Logan he had met a few months ago. Not only was she still with him, but apparently he had cheated on her. The thought of someone cheating on Rory made Jess seethe with anger. He would have given anything to be with Rory and here this guy had her and yet decided to cheat on her. Jess found some inner strength to stand up for himself and he told her "I don't deserve this."
Jess' heart broke seeing the hurt in Rory's eyes as she told him she was in love with Logan. It was like a punch in the gut. Here was the only girl he had ever loved standing in front of him telling him she was in love with someone else. All he could think to say was "It is what it is, you, me…" As much as it killed him that Rory was hung up on some guy that didn't treat her right he still found himself telling Rory she could tell Logan they did something if it would make her feel any better. In the end all he wanted was for Rory to be happy, even if it was at the expense of his own happiness. That was the night he promised himself that he would never put his heart out on the line like that for Rory again.
Jess had kept that promise for ten years. He'd seen Rory a grand total of four times during the last decade. He strategically planned his visits to Stars Hollow when he knew Rory wasn't in town. By avoiding Rory Jess was able to avoid his feelings for her somewhat. His out of sight out of mind strategy wasn't ideal, but it was the best he'd managed to come up with given his predicament. Jess had long resigned himself to the fact that his sentiments toward Rory were eternally twisted. As much as it tortured him to be around her, she was still one of the greatest friends he ever had. Honestly she was outright the greatest friend he ever had. No one else had ever believed in Jess the way Rory had, not even Luke. Rory never gave up on Jess no matter what he did or what he put her through. He admired her for the person she was beyond his romantic feelings for her. Her intellect, her kindness, her wittiness, her drive, these were just a few of the qualities he appreciated most about her. Jess realized he was really sounding a little Elizabeth Barrett Browning "How Do I Love Thee". He smiled because he knew Rory would have appreciated that reference.
Sometimes Jess missed her friendship so much that he would breakdown and visit while he knew she was in town just to get a small dose of Rory, to see her, to talk to her. Those few moments were always gloriously intoxicating, but as it always goes with intoxication – in the moment he knew what he was doing was also slightly harmful. Then the intoxication was always followed by the sobering crash of reality that he'd have to say goodbye to Rory again when he left. They led completely separate lives now. She was on her journey and he was on his. He recently went the longest stretch he'd ever gone without seeing Rory since he'd met her. He had been four years "clean" until this past summer when Luke had called to ask him to help get Liz and TJ out of the weirdo vegetable cult they'd gotten themselves tangled up in.
Since he had to come to town anyway to deal with Liz he couldn't help himself, Jess knew he'd have to stop in and take a hit of the drug that was Rory. He knew she was back, but not really back, she was just between engagements. He had tried to open with a joke when he went to see her at the Gazette as a way to ease his way in. "No cigar?" he had asked. But as she turned towards him all manner of casualness he was trying to convey was lost. The way she looked sitting there at her desk in her element, the way her face broke out into a big smile when she realized that it was Jess standing there, how she didn't miss a beat and replied, "Doctor told me to cut back." It all hit him like a wave and he almost buckled right there.
Still Jess tried to cling to his fleeting nonchalant attitude even though he could feel it slipping through his fingers. He tried to take in other aspects of his surroundings to distract himself as he casually strode in and tried to play it cool with his "Good to see you again, Esther." He hoped Rory couldn't sense his nervousness as he sat down. He piggybacked off what he said to Esther and threw in a "You, too" towards Rory that way he didn't have to come right out with "It's good to see you" and risk revealing more. He couldn't think as fast around Rory. It's like just being near her enveloped him in this haze of edginess and exhilaration that dulled his senses.
It kind of stung a bit when he asked her "What's it been? Four years?" and she responded "Maybe more." like she wasn't really sure. The truth was Jess knew exactly how long it had been almost down to the day, 4 years and 3 months since he'd last laid eyes on Rory. Not counting pictures of course. She wasn't a big social media user and neither was he, but there was the occasional picture on Twitter. She mostly used it for news and work as did he, but he had to admit that it did bring a smile to his face when he got the occasional notification that she had liked his tweet. He also saw her picture next to the byline of different pieces she'd written. Articles he had read almost as soon as they were published thanks to the Google alert he had set for "Rory Gilmore".
It never occurred to him that Rory might have also been feigning casualness when she acted like she wasn't quite sure when their last encounter had been. Rory looked absolutely stunning sitting there backlit with the summer sun radiating in on her and bouncing off her chestnut hair. Before he could help himself Jess found himself flirting with her as he called her "Mr. Roundbottom". He couldn't help but smirk a little when he saw that he'd gotten her a little flustered when he'd taken her by surprise calling her that. She looked relieved when he flipped the nameplate on her desk around to reveal its origin.
Jess kept it going when he toasted her "Roundbottoms up". He knew he was approaching dangerous territory with this flirty behavior but it just came so naturally to them. It was their shtick and had been since they were 17 years old and frankly old habits die hard. Rory was the one who asked him about his personal life first. Jess tried his best to choose his words carefully when he replied, "Stable. Nothing permanent." Rory wasn't making it easy on him as he tried to keep this platonic because next thing Jess knew she was talking about her lack of underwear and he was offering to lend her money to buy new ones. As Rory continued though something suddenly became much more pressing than Jess' struggle to keep things nonsexual, Rory seemed to be in crisis.
Jess was disheartened when he heard Rory describe her life as being in such a tumultuous state. Rory who had always been so precocious, so put together, was suddenly self-deprecating and drinking at her desk in the middle of a workday. It reminded him of when she had dropped out of Yale and that alarmed him. Jess never wanted anything but the best for Rory. She had always believed in him and as he told her when he first brought her his book, he couldn't have done it without her. The least he could do was return the favor. As a writer himself, the thought had long crossed Jess' mind of Rory writing the story of she and her mom. He knew it was a unique story that Rory could bring to life beautifully. Jess was glad when he found out that she had taken his advice about writing the book.
Jess sighed as he stood up from the kitchen table he'd been sitting at in Luke's apartment. He walked over to the sink and rinsed out the glass he'd been drinking from. He stared out the window onto the town square. He looked at the gazebo where he'd outbid Dean for Rory's basket at the Bid-on-a-Basket Festival. The same place where he'd later made out with Rory in the early days of their romance. He recollected how they had both been thankful that neither of them had braces. He glanced at the spot where he and Rory had been standing when he returned her copy of Howl that he had borrowed without asking. He grinned a little recalling the smooth way he responded "Well, what is much?" when she questioned his earlier response about whether he liked to read. He looked down the street towards Doose's and remembered how he tried to kiss her on Thanksgiving that time and how she had pulled him just past the storefront before she would kiss him to spare Dean's feelings.
His eyes wandered over to Gypsy's where he and Rory had kissed by the gas pumps for the first time after they were officially together. That was the moment they had known that no matter whatever else happened between them, at least that part worked. He looked over at what had once been the video store, Taylor had since turned it into some kind of figurine shop once the video store went out of business. It had been just outside there that Jess had impressed Rory when she found out that he had looked up the exact distance of 22.8 miles to Yale. He glimpsed down at the place where he and Rory had stood when he told her that he loved her at the Firelight Festival. Lastly, he looked at the place he and Rory had sat and talked like old times just earlier that night.
Jess turned away from the sink and headed across the room where he took off his watch and placed it on top of the dresser. He unbuttoned his shirt, slipped out of his slacks and got into bed in just his boxers. This was much more comfortable than he'd felt the night before at Liz and TJ's place. He took a deep breath as he thought back on the conversation he'd had with Rory. It had been so easy, so effortless. Then he thought about what Luke had said about Rory seeming interested in him too. It really seemed too good to be true, but he couldn't help but hope that maybe his uncle had been right. After he had shuffled through their entire history that night Jess finally accepted that even though it scared the hell out of him, what he truly wanted more than anything was to give he and Rory another shot. Once he made that decision he knew he'd done enough soul-searching for one night. He had to open the diner in just over two hours so he really needed to try to get some sleep. Rory would surely come in for her caffeine fix and he'd just see where it went from there.