( 𝘨𝘪𝘧: 𝘫𝘦𝘴𝘴 𝘱𝘭𝘦𝘢𝘥𝘴 𝘧𝘰𝘳 𝘤𝘩𝘦𝘳𝘳𝘺 𝘵𝘰 𝘨𝘶𝘢𝘳𝘥 𝘩𝘪𝘴 𝘴𝘦𝘤𝘳𝘦𝘵 )

Cherry was on her home from school, trudging tiredly across the streets of Stars Hollow before she came across Dean. He was stood outside the Gilmores house, scrubbing Rory's car with soap and a sponge. Frowning, Cherry slowly approached, slightly unsure.

"Dean! Hi. What are you- Did Rory ask you to wash her car?" Dean looked up, grinning slightly at his best friend as he wiped the sweat of his foreheard.

"What? No, I was waiting for her and her car looked dirty so I thought I'd wash it." 

Cherry  winced, looking around and noticing there was no lights turned on in the house. "That's  . . . nice of you, Dean. I thought Rory said this week she had this really important school proyect."

He sighed, putting the sponge down. "Oh, yeah. I guess I forgot." 

Silence followed as Cherry shifted her weight. She had a bad feeling for the couple. It had slowly been clearer and clearer that Rory and Dean were drifting apart, and that the blue-eyed girl seemed to always be busy these days, with school and Lane. And that separation seemed to be taking a toll on Dean, as he grasped desperately on the relationship. And that hurt Cherry, because she didn't want to see her best friend hurt.

"Dean . . . did you and Rory fight?"

He looked up, slightly alarmed. "No. Why? Did she say something? Oh God, what did she say? She mad at me?"

"No, no." Cherry interrupted, quickly silencing Dean's nervous rambling. "I just . . . this is just my point of view, so I may be wrong, but it's just seems like things between you are a little off lately."

"I just want things to be like they used to be." Dean said, slumping over as he leaned on the car. Cherry smiled softly, squeezing his shoulder in comfort before patting him.

"Things are always changing, Dean. Maybe try embracing that change. If you try holding on too much to the past, you'll miss what's happening now and get swept away."

Dean grinned slightly, raising his eyebrows at the blonde curly haired girl. "Since when did you get so smart?"

Cherry smirked, flicking her blonde hair behind her shoulder. "Me? Always, you just never listen to me." the two sat in comfortable silence as Dean poured over Cherry's advice. "Well, see you at work. I need to be getting home." before she had a chance to walk away, Dean bit down on his bottom lip.

"Wait, Cherry." the blonde turned around, watching her best friend expectantly. "You're friends with Jess, right?"

She sighed, nodding. "Kind of. And I know you don't like him, but under his cranky old man layers he's actually-"

"Does he like Rory?"

Cherry started to laugh, shaking her head. "Jess? No. I mean, he hasn't said, but I honestly can't picture it. You have nothing to worry about anyways, Rory is very much in love with you." Dean nodded, slightly unconvinced, allowing Cherry to walk away. But as she did, Dean's question bounced through her mind, making her less sure of her answer.

Was it possible that Jess liked Rory?

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Another finished day at school, just as boring and uninteresting as the others. Luckily, the biology teacher had allowed her class to leave a few minutes earlier. Passing through a classroom, Cherry peered in to see Jess sat at the back of the class, reading and scribbling on a the margins of a book while the rest of the class finished an exam.

Jess happened to look up, grinning sarcastically at Cherry. She rolled her eyes, waving at him as she stuck her tongue out. Jess flipped his middle finger up, but as he did, the teacher turned around. He wasn't fast enough, and the teacher crossed her arms over her chest.

"Mr Mariano, may I ask you who you're showing your middle finger to?" 

A few quiet laughs were heard as Jess leaned back on his chair. "No, ma'am. You may not." Before the teacher could scold him, the bell rang, indicating the end of the school day. The other classmates handed in their exam as Jess rushed out, catching up with Cherry as they both walked through the hallways to exit the school.

"You nearly got me in trouble, blonde chewbacca."

Cherry rolled her eyes at Jess, keeping a tight grip of her schoolbooks in her hands. "Me? I was just being a good person and waving at you. Not my fault you're so fucking rude."

"Language. Who knew you had such a dirty mouth?"

She smirked. "Title of a sex tape."

Jess scoffed, nudging her. "As if you've ever had sex."

"Jessica, do you do blowjobs with that mouth?" the two grinned at each other, pretending to be annoyed, when really they enjoyed each other's company. Jess would ever admit it, but Cherry wasn't half bad. "You know, I've talked to everyone in this town and they're much more charming than you."

"That must've taken a while. Are you really that obsessed with me?"

"Not as obsessed as you are with annoying Dean." Jess groaned at the mention of the tall, lanky boy, tugging his dark hair as he played with the pen in his fingers. "Come on! He thinks you like his girlfriend, which is preposterous, really, because you don't like Rory." Jess kept quiet, making Cherry stare at him. Suddenly, Dean's question popped in her mind again, and this time it didn't feel that stupid. "Wait . . . you like Rory?!"

Jess's eyes widened, making sure no one around heard as he shushed the blonde girl. "Why don't you say that louder, I don't think the whole town heard you."

Cherry continued to stare at him as if he was crazy, unsure of what to say or do. "Oh gosh . . . so it's true? Dean's got a reason after all for being so paranoic."

"Cherry, if you keep talking about it I might have to kill you." Jess said deadpanned, making Cherry grin. She finally had something over Jess. Something to threaten him with. She slowly backed away and Jess stared at her.

"Jess and Rory, sitting on a tree! K-I-S-S- oh my god!" Cherry squealed as she started to run, as Jess pursuited her. The two dodged the other students as they exited the school, running through the grass. "First comes a kiss, then marriage, then a baby in a golden- oof!"

Jess pushed her down on the grass as Cherry threw her head back giggling, squirming under his grip as Jess placed his hand on her mouth, making it unable to understand what the blonde was saying. When Cherry stopped squirming, he raised an eyebrow. "Okay, I'm going to let you go now. If you sing that song again, the hand is coming back on. Understood?" 

Cherry nodded stiffly, and Jess removed his hand. The blonde stared at him, all laughter gone. "Do you really like her?"

Jess sighed before laying on the grass next to her. Silence fell on the two as students who passed by looked down at them curiously, whispering between them. "I've never liked anyone before." he admitted, glancing sideways at her.

"Well, that's rotten luck now, that you happen to like a girl who has a boyfriend." Jess turned to look at the sky again, not liking to be reminded of that fact. Jess wasn't even sure if he liked Rory that way. He just enjoyed talking about books with her, and wanted to impress the blue-eyed girl. But was that truly liking someone? He didn't know. "Is that why you've been screwing with Dean?"

"No. I just don't like him, is all." Jess stated bluntly, making Cherry laugh, sighing softly. "I would never kiss her first if she's dating someone else. But she is allowed to have male friends."

"You're right. Sorry."

Jess raised an eyebrow at her. "You've got to promise me you won't tell Rory, or anyone, as a matter of fact."

"I won't . . . if we do a pinky promise." Jess scoffed, shaking his head. Once he saw Cherry was serious, he gave her a deadpanned look before offering his pinky finger. Cherry grinned, wrapping her own pinky finger around Jess's happily. "I promise I won't reveal to anyone the nature of Jess Mariano's feelings for a Chilton girl."

The two sat up, and Cherry grinned as she watched Lane walk by. "Oh, look, it's Lane. Wouldn't she love to know you have a crush on your best friend?"

Jess looked at her alarmed, grabbing her wrist. "Hey! We had a pact. And don't call it a 'crush'."

"And what are you gonna do, attack me with your exfoliating gel?"