( 𝘨𝘪𝘧: 𝘫𝘦𝘴𝘴 𝘴𝘯𝘦𝘢𝘬𝘴 𝘪𝘯𝘵𝘰 𝘤𝘩𝘦𝘳𝘳𝘺'𝘴 𝘳𝘰𝘰𝘮 )

It took a while, but Dean finally convinced Rory and Cherry to have breakfast with him before school.

The trio sat awkwardly at no other place than Luke's Dinner, eating through their breakfast in silence. Dean kept glancing between the two girls, opening his mouth to try and think of a topic of conversation between the two. Cherry was aware of Dean's glances and Rory's fidgetness, giving Jess and Shane a last look, she decided to break the awkwardness.

"So, how's Chilton? I haven't seen Paris in a while."

Rory's baby blue eyes looked up surprise, unsure of whether Cherry was being genuine or not. Last time they had talked, Cherry had snapped in her face about how she had been treating Dean and Jess. And Rory had to admit it ─ she had been. But the casual tone and the small smile on the blonde's face made Rory relax. 

"It's alright. Me and Paris aren't on the best terms right now."

Cherry quirked an eyebrow. "That's a shame." taking a bite of some bacon, Rory realised that Cherry kept glancing at Jess and Shane, but with Dean between the two she kept quiet. 

Sick of the awkward silence, Dean sighed. "Look, you two are the most important girls in my life ─ apart from my sister and mother, of course ─ and I wish you would get along like you used to."

The two girls looked away guiltily ─ they had never been best friends, as their personalities clashed slightly. But they shouldn't have let Jess get in between the two ─  despite their differences, they both cared for Dean. "You're right."

Dean raised his eyebrows at Cherry's words, glancing at his girlfriend unsurely. "Wait─ come again?"

"Don't make me repeat it." Cherry grumbled, making Dean laugh loudly. It wasn't every day Cherry admitted someone else was right. Turning to Rory, she added "Seeing as we'll be spending time together, I would like to amend our friendship."

Rory smiled, curtly nodding. "Of course. I'd like that too."

"This is great." Dean grinned, before wrapping his arm around Rory. "We should go ─ can't have you missing the bus."

Sending them a tight-liped smile, Cherry watched as Dean and Rory leave before slumping over the table with a groan. She appreciated Dean's efforts, but Cherry was someone who liked relationships and friendships that flowed from the beginning. If it wasn't smooth, then she honestly couldn't be bothered. And it was obvious that Rory wasn't too bothered either.

Jess, who had been keeping an eye on the trio once Shane left, grabbed a cloth and approached the table with an amused smile. "God, that was awkward to watch."

Cherry lifted her head up slightly to narrow her eyes at the boy. "I could say the same about you and Shane. Must you make out over the counter? People eat here, you know."

"Jealous, much?" Jess asked amused, quirking an eyebrow slightly as he picked up a few plates. Cherry scoffed as he left the dishes in the sink before turning to her. "I guess I shouldn't mock those who haven't been kissed though."

Sniffing with her nose tilted upwards, Cherry straightening her posture she scoffed. "For your information, I have been kissed. Plenty of times."

"Aha." Jess said, a mocking tone to his voice. His back was turned to her, a dirty cloth hanging over his shoulder. "I'm sure it's with time that lying comes so easily to you."

What Cherry did next haunted her for the rest of the day. She wasn't sure whether she had thought it through, but by the time she had realised what exactly she had done, it was too late. The blonde knew her temper and her impulsiveness got the better of her, and with Jess's relentless teasing, the built-up tension from her conversation with Dean and Rory, her confusion about her feelings for Jess and her need to prove herself made Cherry grab the front of Jess's shirt and pull him down. 

Jess stumbling forward, he was caught in a surprise when his lips landed on Cherry's. The moment was short, not long enough for Jess to realise and respond to the kiss. Yet as she pulled away, the raven-haired boy was aware that the particular moment would keep him up awake at night with a smile on his face. 

With widened eyes, he stared down at her, unable to splutter out a full sentence. A similar, perplexed look flashed across Cherry's face before she straightening her posture. Grabbing her purse, she smirked at him. 

"Now you know." Jess stared at her as Cherry left the dinner, unaware that Cherry was outside smacking herself mentally for doing something like that. He lifted his fingers to slightly touch his lips, a scoff and a smile possessing his dark features. 

Lorelai, who had been watching in a subtle way, tilted her head with a thoughtful, pensive look on her face, before downing her coffee.

Her perception of Jess changed slightly.

∎ ∎ ∎ ∎ ∎ ∎ ∎ ∎ ∎ ∎ ∎ ∎ ∎ ∎ ∎ ∎ ∎ ∎ ∎ ∎ ∎ ∎ ∎ ∎ ∎ ∎ ∎ ∎

Jess Mariano had found that it happened to be his lucky day.

Of course, if you asked him, he wouldn't say out loud that the kiss that Cherry had given him was on the list of good things that had happened. But the memory of it definitely replayed over and over again in his head. 

However, finding a ladder to the side of Cherry Doose's window was considered extremely lucky. Jess didn't fancy having to climb the weak-looking vines that crept up the white-bricked wall. Making sure that the ladder was sturdy, Jess began to climb, aware of how cheesy and cliche this appeared to be. Inside, he could see Cherry drapped across her bed, book in her hand as her legs swung to the side.

It only took a sharp knock on the window for Cherry's green eyes to notice Jess. She pushed the window open, blonde locks falling into her eyes as her inquisitive look pierced into him. "Jess, what the─"

"Are you going to let me in, or what? It's freezing out here, and my legs are starting to ache." the tone in his voice was light and breezy, and after a moment of hesitation, Cherry moved to a side, allowing him to climb through.

Once inside, Jess allowed himself to look around before sparking up a conversation. The room wasn't enormous, but at least she had one. The walls had been painted a sage green, but one couldn't tell from all the amount of things that hid the painting. Pictures of Cherry through-out her life, with her toothless grin and childish gaze. Posters of Matthew Perry and ABBA vinyls were plastered on the wall with sticky cellotape. Many shelves with books and CDs stacked on top, with some names Jess recognised: Austen, Bronte, Dickens, Hardy . . .

"Are you actually tell me what you're doing here, or are you going to keep playing Romeo?" Cherry spoke up. She had been watching him carefully, an unsure look on her face as her arms crossed across her chest left her guarded. 

His gaze met hers, denim jacket and hands dug into his pockets. Shrugging his jacket off, he laid on the bed, and Cherry cursed herself for blushing. "I think we should talk about a certain . . . kiss, that happened between us."

"There's not much too talk about. I only did it to shut you up, it didn't actually mean anything." Cherry dismissed it, playing with the edge of her sleeves. When Jess failed to response, she turned to glance at him, a far-away look in his dark eyes. "Right?"

"Right." Jess replied, a bit too sudden, as if a rehearsed lie. Before Cherry could question it, a knock echoed across the room. 

"Cher, you there? Can I come in?" Bethany Doose's voice rang, causing Cherry to tense up alarm.

Grabbing Jess's sleeve, she pulled him up to stand before pushing him inside her closet. "Be quiet." she hisses, and as she shuts the door, Jess's amused smile being the last thing she sees before Bethany opens her bedroom door, quirking an eyebrow at Cherry standing unnaturaly in the middle of the room. "Mother! What brings you around here?"

"Who were you talking to?"

Cherry hesitates for half a second, before laughing. "Huh? Myself. Who else?"

After a long look, in which Cherry was convinced her mother could see through her act, Bethany shrugged, sitting at the desk. "Sebastian has been asking about you."

Cherry groaned, jumping backward unto her bed. Her and Sebastian had met a year ago at a gathering ─ his mother and her mother had been high school friends, and both hoped him and Cherry would one day date. And while Cherry liked Sebastian well enough ─ and she was sure he would say the same about her ─ they had no interest in pursuing a romantic relationship just to please their mothers. If the time came, it came. But it hadn't so far.

"Ugh, you bring it up every time. How many times do me and Seb have to tell you ─ it's not like that."

Bethany opened her mouth to protest, but under Cherry's glare, she shut her mouth. "Fine. What about any other boys, or girls, I don't mind." The blush that Cherry attempted to hide made Bethany sit up straight, inquisitive look on her face, blue eyes noticing a jacket on the floor. "Does that blush have anything to do with the owner of that jacket?"

Cherry widened her eyes, glancing quickly at the closet ─ Jess hid inside, and hopefully he hadn't heard that. It was his jacket, after all. "Maybe we could have this chat another time, mom─"

"Why must you conceal your feelings all the time? Surely it gets tiring." something in her mother's tone made Cherry snap.

"Because the person I like doesn't give a damn about me that way!" Bethany widened her eyes at her daughter's tone, but now that she had started, Cherry couldn't stop. "Unlike you, who seems to be unaware that you're breaking hearts, I face unrequited feelings, and I would rather if you stopped making me face it because it hurts enough as it is!"

Bethany stared blankly at her. "What's that supposed to mean?"

"It means that what you think is casual flirting, hurts the men that you're leading on!" as soon as she shouted it, Cherry pressed her lips together. "I'm sorry. It has nothing to do with me ─ I shouldn't have said that."

Bethany's eyes glanced at the closet, a knowing look on her motherly face. "It's alright. Maybe we should have this conversation another time."

After a nod, Cherry groaned as her mother shut the door. Jess slowly opened the closet door, his head of messy dark hair and curious eyes appearing from a side. She leaned her head on her arm, pushing herself up. "How much of that did you hear?"

"Not much." Jess lied. "It all sounds muffled from in there. Just some shouting, but . . ." Cherry watched him carefully, nodding unconvinced as he avoided her gaze. "I should get going."

Grabbing his jacket, Jess made his way to the window. He hesitated, before leaning down and pressing his lips unto Cherry's cheek. She suck in a breath, eyes wide. Pulling away, Jess nodded before climbing out. Cherry softly touched her cheek before smiling, shaking her head. 

Once Jess arrived back to Luke's home, and the lights were turned off, leaving it pitch black, and he laid in his bed with only his bottom half dressed, he recalled the kiss of this morning. The scent of lavender of  Cherry's perfurme, the taste of her chapstick and the soft feeling of her plump lips against his own.

It was going to be rather hard to fall asleep that night.

i can already IMAGINE all of y'alls reactions to this chapter

who expected for cherry and jess's first kiss to be like this? i promise their next kiss will be better, though it might not happen for a long while