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It’s not that Rory Gilmore wanted to kiss Jess Mariano. Really. She didn’t want to do that. She could think of a million things she would have done before ever doing that: Being in The Titanic just before the wreck, becoming stranded on a deserted island with Taylor Doose, doing something embarrassing in front of the whole assembly. Kissing Jess Mariano was NEVER on that list.
But she had to kiss him. For her art.
Just very recently, in an attempt to blend in with the Chilton crowd, Rory had joined Prose Pros - a story writing club. She would have joined Franklin - the Chilton newspaper but there were simply no spots. So it was either writer club or sports and there was no way in hell, Rory would ever pick sports.
And it wasn't like she hated it.
In fact, she found it quite lovely. Reading had always been one of her passions. And to use all of her reading to fashion something imaginative, creative seemed poetic to her.
Each week they spent doing something new; Rory usually always dedicated her time to narrative writing or drama. But Miss Davis - their instructor insisted that the children hone writing in all genres. So this time, Rory had to write a sappy romance.
Now you see, even that wasn't a problem. It was just that Miss Davis frequently kept healthy competitions between students. This time, for the winner of the assigned romance story, Miss Davis promised extra credit helpful for their college application. Rory liked the sound of that.
But mostly what prompted Rory to really, really want to win was that Paris Geller was also part of the competition. And when it came to her, nothing could be considered healthy. Last time, in the poetry contest, Paris had beaten Rory; Excruciatingly. It was Rory's turn to make it up for it.
She made her way from the bus stop to Luke's Diner, smiling to herself, and occupied a seat near the window far from any mass; with pen and paper in her hand. The outline of the story was quite simple, she had formulated it all the way home on the bus - a tragic romance where the heroine is serving as a maid to a prince she had known since they were both children. The prince is in love with her but is forced to be engaged to someone of his merit for the sake of the kingdom. Then followed the exploration of their struggle with their feelings and the risk their relationship would entail.
It was all very devastatingly beautiful. It flew out of Rory's pen as wind breezing through the hair. But then Rory found herself at the climax. The prince took the maid into his arms…And then... Rory didn’t know how to continue.
She, of course, knew what should happen. They would share the most passionate kiss ever written in history; after all, all the tension she’d written had been leading up to that. But she just...didn’t know how to write it. Rory was sixteen years old and was never kissed before. Not that it was a fact she ever let her mind dwell on, but now that very fact, was affecting her writing.
She had read about kisses, sure. But if she were to base her writing on only that, it would be taking the words of others. And number one rule Rory had learnt in journalism was to check the facts. And for all Rory knew, all those other people had been lying and kisses weren’t as magical and life-changing as they had made it out to be.
And she knew she couldn’t ask for the opinions of the people she trusted the most. Not for this assignment. Last year when her mother Lorelai got the slightest whiff of Rory thinking about boys, they had been in a big fight; none like any they had before. As for Lane - her best friend, she had been set up for over fifty dates with potential doctors but none of them dared enough courage to muster a kiss. Well, there was one boy who kissed Lane on the forehead but that was no use to her now.
But she was determined to beat Paris Geller at the short story competition and in order to win she HAD to write a convincing kiss from experience.
She looked around the almost empty Diner - it seemed far from probable to consider Luke had ever kissed anyone; Miss Patty certainly could help her, giving out all the gory details but that wasn't with the risk of the entire town finding out Rory asked about being kissed. So that left her with the only option she had: she had to kiss somebody herself.
And she knew it had to be Jess.
Again, not because that was what she wanted but because it seemed to be her only choice. Jess was the only logical option. The boys at her school always found a way to ignore her (for which she was actually quite grateful). And there was no way she would kiss Tristan. She could already imagine the dirty smirk on his face if she even dared to approach him. She thought briefly about asking boys from Stars Hollow High but knew that she probably wouldn’t even feel a spark considering their non-existent relationship.
Again, stressing the fact that Jess was not a choice of the heart. Quite frankly, He wasn’t even a choice. He was the last resort.
A feeling started in the pit of her stomach, almost like a flurry of snowflakes, as her mind wandered about kissing him. But there was really nothing else she could do. That night she had gone to bed thinking about how she could bring up her predicament to Jess the next day after school. Which was considerably easy, given that Rory and Jess liked to hang out near the bridge quite often.
Jess Mariano - Local grumpy Luke's nephew who had recently moved into town loathed every minute of it. He hated how involved everyone was in others' business, he hated how anywhere he went he would meet at least five friendly faces and mostly hated the fact he wasn't wanted by his own mother.
He often found solace in his heart when he sat by the bridge. Which in the beginning, was troubling to Rory, as that was her secret spot. It was isolated, quiet and beautiful. Seeing him there irked her. But he never approached her. He would always throw her a pleasant smile when she came in and would spend the rest of his time buried inside a new book, legs hanging below the deck.
At first, they mostly ignored one other. But once when Jess was reading The Bell Jar, Rory couldn't help but butt in, to know his opinion. That's how they had become friends. She found him pretty insufferable at times with him defending Hemingway and calling Ayn Rand a political nut. But it was all healthy banter. It wasn’t the most conventional friendship but a friendship, nonetheless.
No, finding him alone wasn't the issue. The difficult part was how she would word her quandary to him. She had to make it extremely clear that what she was asking him to do was not an invitation of romance, but merely a favour for a friend for sake of their art.
Rory, after much trial and error, came up with a speech and practised it over and over again.
She practised it in her sleep. She practised it in front of the mirror as she got ready for school. She practised it in between bites of Luke's french toast at breakfast. She practised it as she walked out of the door to go to school.
She practised it again and again and again.
Jess, I need to ask you for a favour. I ask this to you in the strictest confidence, hoping that you would be a good friend, and dare not laugh at me. I am writing a romance story for a competition at Chilton, which I desperately need to win. The two characters of my story are at the peak of their romantic venture and they must share a kiss, but you see, I’m stuck seeing how I’ve never been kissed and I don’t know how to accurately describe one. So What I’m asking you is, if you could be mature about it and kiss me... so I can continue writing my story?
But the second she saw him, it all went out of her mind.
He was behind the counter talking to Kirk, looking unfairly handsome, as he grumpily scrawled down Kirk's neverending order. Rory didn’t even know how she had made it to a table without tripping while having all of her attention focused on him. Focused on his lips and the thought about how they could possibly be on her own lips in a few hours, that is if everything went right.
She spent the rest of the time, drinking her coffee, focused on him. It was extremely unfair to Lane, who was reciting a possibly hilarious story about her school, that Rory's mind was elsewhere. It was just that she couldn’t help it.
She was an imbalanced mixture of nervousness and excitement, and it only seemed to edge as she was finishing her coffee. She found herself sneaking glances about every second, looking at Jess as he delivered orders, completely oblivious to her.
It wasn't that she hadn’t noticed him before, but suddenly, she seemed to be hyper-aware of his existence and to all his features. The sharp jaw. The slight vein popping out on his left hand. The long eyelashes.
His curls.
Rory, who wouldn't admit it even in her dying breath, had often found his curls to be the object of her daydreams when she was in deadly boring history class and her mind wandered without any self-judgment. She imagined what it would feel like to twirl one of his perfect brown strands around her fingers; about how it would feel to run her hand through his hair, to have the softness of it in between her fingers, But Lane broke the daydream by poking her side.
“Rory, you’re spilling,” she whispered, pointing to the ketchup all over the table.
“Shoot,” Rory said, trying to wipe it out with a plethora of tissues. Just in time for Jess to swoop in, "I got this, you alright ladies?"
Lane looked at Rory, obviously concerned. Rory announced, “I’m perfectly fine, Lane". Lane gave her a polite but curious smile and Rory thanked her graciously in her mind that she didn’t push the subject any further.
Jess wiped the table cloud white and fidgeted with the cloth, eyeing Rory "I'll see you… Later?"
Rory gave a nervous nod.
It was the same plan almost every day, like clockwork. They would meet up at the bridge and hang out there talking about everything, anything and nothing. Jess even sometimes brought treats from Diner which pleased Rory to an extreme level. In the end, he would politely ask if he could walk her home. Her answer had always been yes. Lane had even gone out on the limb with the suggestion that he would ask her out soon. Rory, although a bit appeased on the inside, cringed awkwardly for all exterior matters and purposes at the ridiculous suggestion.
They got up from the table. Lane went to pay as Rory proceeded to put on her coat, feeling the same fluttery feeling she had felt the day before at the thought of kissing Jess.
As always, Jess was waiting for her at the deck, hands in his pockets and one leg crossed in front of the other. He smiled as Rory stepped in his sight while Rory tried her hardest not to blush.
“Good weather today,” Jess commented, his smile still wide.
“Positively beaming,” she smiled back, stepping down to meet him.
They sat down in their usual spot, books in their hand, legs hanging below the deck. Silence enveloped them. Which wasn’t out of the ordinary but one could smell the tension between even from a mile away. Rory stayed quiet because she didn’t know what to say, how to bring that up. She was mostly afraid that if she opened her mouth only a nervous blabber would come out. Jess stayed quiet because...well, he was Jess.
Luckily for her, Jess took it upon him to break the ice, he teased her “You’re awfully quiet today” Rory looked up to see his twisted smile, eyes loaded with nothing but concern. He bumped his shoulder with hers. “What’s eating you?”
“Jess -,” she started, finding herself completely distracted as he sat there, gazing into her eyes; listening intently. It was at that moment, that the whole speech she had written and practised went down the trash can and she blurted out, “Kiss me.”
As she sat there, agape, drowning in the embarrassment of what she’d said, Jess’ eyes were still wide, comprehending what she had just asked. His face beamed brighter with every second, as he inched close to her “What?”
Oh god, she just wanted to absolutely perish on the spot. Given any moment, if she were to be asked when she would prefer a zombie apocalypse/Asteroid attack/Getting hit by a bolt of lightning - an answer in unison would be this particular dreaded moment. It took her energy of all the thousand suns to fight off the rose mounting her cheeks.
“You don’t have to,” she began, flinching at the desperation and the decomposition that her voice served “It’s not like I want you to. I just need you…you’d be doing me a favour, you know? As a friend…I consider you a friend! And this would help me write because I need to write about a kiss but I don’t know how that feels because I’ve never been kissed before and it just seemed like a good option to ask you to kiss me -”
And whatever else gibberish that was scheduled to drop out of her mouth never did. Because instead, Jess closed whatever little space they had between them; Cupped her face in his hands and planted his lips on hers.
It was as though everything around them was frozen for the moment. She felt her defences sinking as her arms automatically found it’s way tugging his jacket for support. She simply closed her eyes, letting herself be pulled away by the whole experience.
She had been scared for the longest time about whether she would do it right but at that moment, none of that mattered. All her concerns washed away as she was completely immersed in whatever fuzzy feeling that she was feeling in her stomach, how his hands softly held her face as though it was the most delicate thing in the world, and how their lips meet over and over again - something so tender, something reminiscent of a perfectly choreographed dance.
In that nanosecond, Rory understood why there were so many songs and poems dedicated to kissing. It felt like all the power in the world came together to make this feel alive. She was overwhelmed with a surge of magnitude of emotions. Like flowers blooming around her heart. Like a swarm of butterflies had made their way onto her stomach...
At that moment, she knew she was supposed to be kissing Jess. It really was that simple.
He was the first one to pull back. Rory opened her eyes to find a dazzled looking boy, holding a breathless smile with his pink tinted cheeks. She wondered how she could face him now. He stood there, one hand still enveloping her cheeks as the other tucked a piece of her hair behind her ear. He began, his voice dripping with amusement. “So, at least now we figured out a way to get you to stop talking.”
What she had been thinking was that if this was his method of shutting her up, she would never stop talking . But in reality - her mind and body didn’t cooperate with each other, leading her to march away, hastily.
He was quick in action to get up and catch her by her slippery sleeve, still laughing a little bit “ Rory, c’mon. I was only joking, I just thought it was a little surprising that you asked me to kiss you”
“Well, you certainly didn’t need much or any convincing at all” she retaliated, crossing her arms and looking at him in an accusatory manner. This time it was Jess’s turn to become speechless, “Yeah, well like you said,” he faltered. “It was a favour. For a friend. For her... art.”
“Right,” she nodded.
They both avoided looking at each other until Jess spoke up again.
“So did it help?” he asked, clumsily rubbing the crook of his neck “Are you going to be able to write it now?”
“I think so,” she calculated as an unhinged idea popped in her head, “But there are different kinds of kisses and I just... feel like I should be well versed in all of them just for future reference. What say you?”
It was astounding how still she looked for all of the outside world but inside she had melted into a puddle of nerves. But thankfully, for some reason, he looked impartial as though giving her proposition a real thought. He gulped and nodded, “Yeah, I totally agree. I can help you then, you know?... Just so you can have all the information you need.”
“It’s a plan,” Rory smiled casually. “We can finish this tomorrow. I’ll be walking home myself today, thanks”
She found Jess squirming as he struggled to hand over the bag of croissant he had brought for her. Rory realized she had never seen him squirm before, it was entertaining.
“I’ll see you tomorrow then” She nodded once more and turned around to continue walking home, practically hopping all the way there. Do you ever watch in movies how the main characters are skipping and singing on roads when they were too happy? That was Rory, at that moment. She quickly said hello! homework to her mother before racing to her bedroom, collapsing onto her bed with the widest smile on her face.
There was always this irrational fear in her that she would end up dying a spinster. But now at least, she won’t die being unkissed. She had been kissed and it had been the most magical, romantical moment of her life thus far. (Not that she would ever admit that to Jess)
Another thing she wouldn’t tell him or any other soul for the matter of the fact was she stayed sleepless all night consumed by the thoughts of kissing him again. Various times. Sometimes in tulip fields; sometimes in her mother’s inn; Sometimes at her school dance.
The next day, Rory was just a pinch away from a jittery ball of nerves before school; She outright refused to dine at Luke’s in the morning hoping to avoid an awkward bumping into Jess. Lorelai, who was concerned at that point, questioned her about it. Rory was quick to dismiss that anything was wrong and just blamed it on a pop quiz. But Lorelai being Lorelai and Gilmores being people who can’t cook, Rory had to visit Luke’s.
When she entered the diner, she saw him talking to a couple of customers on the other side of the room. She saw how he stopped talking to look at her and how his smile became softer and shyer. It made her smile too. Truth was, on the inside, her heart was bursting.
Lane who met the mother-daughter duo there casually mentioned that Rory looked more vibrant that day. “I feel much more vibrant too, Lane” Rory declared, stealing only one final glance towards Jess before picking up her waffle and running out of the diner. He would be waiting for her at the end of the day anyways.
The afternoon sun was bright, perfect spring weather for the budding feelings of oblivious teens when Rory saw Jess sitting near the deck.
“Hello, Jess,” she greeted him.
“Hello, Rory,” he said back, smiling.
Rory silently occupied the seat next to his. Jess leaned in, “So are we here for more ‘inspiration?’”
Rory nodded eagerly, bringing out the empty paper and pen from her bag in front of his face. Jess’ face was highly amused “First, I must finish the story I was writing and then your inspiration will be needed”
“Okay,” he smiled, reaching towards his own copy of Howl. They stayed there, the two of them sitting in silence while she worked on her assignment and he read their favourite book. It takes her almost an hour to finish her story. She takes out another blank sheet of paper and writes in bold letters “Types of Kisses”. She lists the first one - a peck. Rory puts down her sheet of paper, turns towards Jess, sitting cross-legged “Jess, I’m ready now,”
He put his own book down and mirrored her sitting, a smirk on his face that, as skittish as it was, still made her stomach do four hundred somersaults. He teased her, “And how shall I be kissing you today, Miss Gilmore”
“Just a peck,”
She sat up straight to better prepare herself. He, too, aligned himself to get a clear view of her as he leaned in and quickly kissed her. It lasted hardly a second, but it was sweet and warm enough to melt her heart.
“Thank you,” she said politely, and then turned back to her paper. He only laughed and shook his head at her before turning back to his only work. While he dove back into his astute poetry, she wrote about how a peck was like a spark of electricity, small and quick but still powerful enough to light her heart on fire, enough to make it skip a beat and instigate in her that she was, in fact, very much alive.
Jess looked at the greying sky, “It’s getting late, You’ll miss your curfew”
Rory nodded as she gathered all her scattered papers “I really appreciate you helping my writing, Jess.”
“What are friends for,” he said, grinning.
The entire next weekend was spent around the theme of kissing. Jess showed her several types of kisses as she hungrily wrote it all down.
After the events of that week, two things were certain - one) Jess was copiously experienced when it came to matters of romance and kissing which made her feel insecure that somehow, she wasn’t up to par. But he always looked at her, eyes shining, like she was the only object of his affection; like she was the one who hung up the moon; like she was the one who fueled the sun to shine as much as it does and all that melted all of her insecurities. two) she really, really liked kissing Jess Mariano.
And for the next few days after that, Rory found herself writing about other of Jess’ qualities, his subtle mannerisms, and not just about his kisses. Although, she enjoyed any kind of writing as long as it was about him.
She wrote about how when he hardly smiled, but when he did, tiny dimples crept up and it would reach up to light his eyes and everything surrounding him. And she also wrote about the way his lips would toy a coy smirk after he winked at her from across the Diner when no one was watching.
She wrote about how it felt to have his mouth laughing in her ear whenever she went out of the way to mock his taste in movies. And she also wrote about the way she noticed he would sometimes play with his hair, rubbing it in between his fingers, when he was nervous.
She wrote about how it felt to have his eyelashes brush against her cheek as he leaned in for soft kisses. And she also wrote about the way he looked at her, eyes wide and curious, when she pulled him closer tugging his jackets.
She wrote about how it felt to have his nose rub against her own, which made the both of them giggle. And She wrote about how it felt to have her hand come up behind his neck, bringing them closer together.
She also wrote about how he always jumped at the opportunity to open the door for her or help her with her things. And she also wrote about how he had been one to make her feel safe, knowing that he wanted her to succeed and would never judge her for any of her quirks.
She wrote about how it felt to have her fingers wrapped under his palm, his thumb rubbing back and forth across her knuckles as he brought her hand up to his mouth to place a kiss on it. And she also wrote about how she noticed he walked closer nowadays, and how their fingers always brushing against one another.
Nothing. Nothing in the entire wide world could be possibly compared to the way Rory felt when she kissed him one last time that one afternoon when she had decided to put a full stop to her ‘Kiss research’ project with Jess. She could swear that his eyes, just for a second, immersed into depths of despair. But he was quick to recover, he shook his hand with hers as they do after completion of a successful something and headed to walk her home anyway.
It was that day when Rory had to hand in her story. She did so too, eagerly, reminiscing all the memories that paved the way for this story. It didn’t matter that she didn’t beat Paris. It didn’t matter that a kid named Brad actually won the competition. It didn’t matter that she quite possibly lost an important extra credit. At that moment, it all seemed futile. Her petty rivalry with Paris Geller, her petty project to one-up Paris - everything seemed inane compared to the big thing staring right at her face.
Her feelings for Jess Mariano.
It hadn’t even been forty-eight hours since they bid adieu and parted their ways and Rory had spent forty-seven of those hours engrossed in thoughts of him. She climbed off the bus, her brain still processing events of the past few days when she spotted Jess by the gas station. Something in Rory’s brain settled as she looked over to him; He looked handsome, unbelievably and effortlessly handsome.
She was transported back to the first day they met and he pulled a stupid magic trick to amaze her. While she wasn’t impressed by the stunt, she still stayed curious about him. The time they parted ways after their first civil conversation ending with her wishing him ‘goodnight, dodger’ was embossed in her mind without any imposition. She remembered how much she’d missed him they hadn’t seen each other in those past two days. How deeply her soul wished that he would come back? How deeply she wished they had been playing spin the bottle and the bottle would land on him? Just how deeply she just wanted to… kiss him.
If she wanted to kiss a boy, couldn’t she just kiss him?
Looking then at Jess, there was nothing she wanted more. Before she could stop herself, she found her legs making their way to where he stood. She came at a halt in front of him, “So, I didn’t win”
“Sorry, our experiment was a big fail”
He had barely registered her being there when she raised her toes, grabbed the ends of his jacket in both hands, weighing him down, and kissed him. Having her lips crash onto his, she realized how much she had missed this, and how perfect this felt. She could sense the smile creeping onto his lips and felt herself begin to smile too.
“What was that for?” he asked, his eyes delving into her pools of the ocean blue.
Rory laughed a little, as she toyed with the ends of his jacket and gave him a playful shrug “That was just for me.”