AN: This story was initially supposed to be a fluffy oneshot for the #simplysnowbarry2018 challenge on tumblr, but it evolved into a much bigger project. Hopefully it still meets the requirements of the prompt.

Shout out to the talented, fantastically-helpful eccacia for her constant help and dedication to making sure this project isn't awful. Thank you for being the best beta ever!

Feel free to leave feedback, positive or negative. I appreciate all of it. I hope you enjoy!

Barry wraps his uneaten sandwich in plastic, stuffing it back into the lunch bag. He's not really feeling the ham and cheese.

"Ay, you gonna finish that?"

Cisco's hand is already stretching toward the bag. Barry narrows his eyes but lets him take it nonetheless. He devours it so quickly that Barry wonders if he even got all the plastic off first. Some of it's probably gonna end up in his digestive tract.

"Jesus, dude, chew before you swallow."

His advice falls on deaf ears as Cisco burps and tosses the plastic into a nearby trash can.

"Hey," he says after wiping his mouth. "You ready for spring break?"

"Definitely. Can't wait to sleep in till noon and not leave my room for a week."

Despite the sarcasm lacing his words, Barry is genuinely pumped to do just that. He needs sleep more than he needs some extravagant vacation.

"Funny. What about the beach trip?"

"What about the beach trip?"

He blinks.

"What do you mean what about the beach trip?"

"What do you mean what do I mean what about the beach trip?"

"What do you—" Cisco shakes his head. "Barry!"

"Cisco!" he exclaims with disinterest.

"You know the beach trip is next week, right?"

Barry rolls his eyes. Of course he knows. Every student in Central High knows. The beach trips are legendary, epic, magnificent.

And they're completely unappealing to Barry. Call him crazy, but he doesn't want to drink himself to sleep for two days, or start a hundred-man fist fight on the beach, or snort enough cocaine to lift a car, or have sex with seven of his classmates.

Not that there'd even be opportunity to do those things. The stories would say otherwise, but as far as he's concerned they're all lies propagated by easily-excitable freshman.

"Yes, Cisco, I know," he states matter-of-factly. "I'm not going."

Cisco slams his fists on the table, always the melodramatic one.

"Bartholomew Henry Allen, what in the hell do you mean you're not going?"

"That," he says. "I mean that."

Cisco facepalms.

"Dude, come on! You can't just bail on the trip!" He says the words like they're some kind of sacred, biblical phrase. "It's a once-in-a-lifetime opportunity."

"I'm sure I'll have plenty of time to drink and make poor decisions."

"Not like this!" He takes a deep breath. "Okay, look, you can drink away your midlife crisis all you want, but that's not what this trip is about. This is your opportunity to run away for a week! Shirk all responsibilities! Live in the moment!"

"Exactly why I don't want to go." Cisco groans. "Crazy drinking and meaningless sex aren't fun."

"Spoken like a drinkless virgin."

"Takes one to know one."

"You'll get it when you get there," he continues. "Just gotta feel the vibe."

"I'm not going."

"Yes, you are. Especially when a certain handsome bachelor needs your help."

Barry sighs.

"What do you need now?"

A wide grin spreads across Cisco's face.

"I'm so glad you asked." He throws an arm around Barry, who attempts to squirm away. "Because this next week could be the greatest week of my entire life."

Barry thinks about it for a few moments.

"Isn't that kind of sad?"

"What? No!" Cisco shakes his head. "No, it's going to be amazing is my point! Why do you always miss the point?"

A silence follows and Cisco looks expectantly at him. Barry rolls his eyes.

"Okay, fine, I'll bite. Why will be amazing?"

"You, my friend, are going to again fill the role of greatest wingman in the history of winged-men."

Barry groans.

"Not this again, Cisco."

"No, no, it's different this time, I promise!"

He narrows his eyes.

"Last time I was your wingman, Snart almost killed me! He thought I was trying to get with his sister!"

Barry swears he has a permanent bruise on his stomach from when Mick and Leonard beat the hell out of him. He thanks his lucky stars they're in juvie, far away from his precious, delicate stomach.

"Actually that was two times ago. Kendra was the last one, remember?"

Ah yes, the time when Kendra's ex-boyfriend came after Barry because he thought he was trying to get with her.

(Noticing a pattern yet?)

Barry stares blankly at him.

"Alright, sorry. I owe you one for taking the fall for me with Carter and Rory and Snart."

"More like you owe me five. Or ten. Or a hundred-thousand."

"But I'm not trying to get with Lisa or Kendra anymore! This is different!"

Barry raises an eyebrow.

"I'm going after Gypsy!"

He blinks, not even attempting to match Cisco's overly-enthusiastic expression.

"Why are you looking at me like that?"

"No. Way. In. Hell—"

"Oh come on, Barrryyyyy, please?"

"Also she hates being called that. And I'm pretty sure it's a race thing too, so maybe don't use it, like, ever."

"Gypsy can mean a nomadic or free-spirited person!"

Barry stares at him for a few moments.

"Have you been Googling things related to her?"

"Pretty please with cherries on top?"

Barry exhales heavily, rubbing his temples.

"Okay, first of all, you know her dad is in jail, right? You want him to come after me because he thinks I'm hitting on his daughter.

Cisco rolls his eyes.

"Come on, there's no way that'll happen. And I'm sure he's in jail for something totally chill. Like tax fraud or money laundering or something."

"How is tax fraud… y'know, I'm not even gonna touch that one." He shakes his head. "Second of all, if her dad doesn't kill me, she will. Or maybe she'll kill you. Or both of us at the same time."

"Ridiculous. Who could kill this face?"

"Plenty of people," Barry is tempted to say, but he holds back. "Remember when she was suspended after she started that fist fight?"

"Everybody makes mistakes."

"Or when she vandalized the school?"

"Postmodern art."

"Or when she set a trash can on fire?"

"Art takes many forms."

"Or the second time she got suspended after she started another fist fight?"

Cisco pauses.

"That's kinda… beside the point."

Barry slaps a palm to his forehead.

"Cisco, how is any of that beside the point? I am gonna die. You are gonna die. She's gonna kill both of us, and she's going to enjoy it."

"She will not and—" His eyes go wide. "My heart be still, there she is."

Barry follows his gaze and finds Cynthia stomping through the lunchroom holding a brown paper bag. Or perhaps she's just walking normally. Barry can't really tell; everything she does is sort of stompy in a way.

"You're on your own," Barry says.

"Come on, I'll do anything for your help."

"Okay. Stop trying to make me come on the trip."

"What? No, that doesn't… Barry! That defeats the purpose of asking for your help!"

"You said you'd do anything."

"Why does Cisco need help?" Caitlin's voice startles both of them. Barry perks up. He was concerned when he didn't see her in chemistry. Although it's not unusual for her to miss class periods. Sometimes she skips whole days. Not that anyone can blame her after what happened.

Cisco's face is immediately awash with concern. "Hey, Caity, you okay? I didn't see you in homeroom. Everything alright?" Caitlin's expression stiffens and Barry sighs. He knows Cisco means well but his lack of tact isn't what she needs right now. She just needs normalcy and Cisco seems to think that constantly asking what's wrong will help.

"I'm fine," she says quietly.

Cisco opens his mouth to continue but Barry jumps in.

"Cisco is trying to get with Cynthia."

Caitlin's nose scrunches up in disgust and Barry smiles.

"You're going to get yourself killed," she says.

"See? I told you."

Cisco rakes his hands through his hair.

"Come, don't gang up on me! I need help, not hatred!"

"You're such a drama queen," Barry says.

"Don't leave me hanging. What kind of best friends would leave me to my fate like that?"

"So you admit she would totally kill us?"

"Not the point, Barry!"

Caitlin chuckles, running a hand through her hair. Her startlingly-short hair. Barry does a double-take as the difference in her appearance finally registers in his head.

"Hey, you got a haircut." Her eyes drop as she continues twisting and turning her curls. "I like it."

"Thanks," she says with a shy smile.

"Caitlin," Cisco butts in, "please tell Barry he needs to be my wingman."

She turns to Barry. "Barry, you need to be Cisco's wingman."

"I disagree."

She turns back to Cisco. "Well, I tried."

Cisco lets out an undignified noise.

"Okay, how about this. If things don't work out with Cynthia, I'll pay you fifty bucks."

Barry's eyes widen.

"Are you serious?"

"Dead serious. Fifty bucks. Just come on the trip with me."

Cisco stretches out his hand.

Barry purses his lips. Fifty bucks doesn't sound bad. But going on the trip doesn't sound good. He knows himself, and he knows how impulsive and thoughtless he can be. Mix that with alcohol and partying and peer-pressure and he knows he could easily get into trouble.

Then again, the same goes for Cisco. Possibly even more so. He's more impulsive, more thoughtless, and, arguably even worse, he's 100% susceptible to 'the vibe.' He'll get caught up in the moment and do some stupid shit and will probably regret it forever. Unless Barry's there to keep him straight.

If not for his own enjoyment, Barry owes it to Cisco not to let him end up dead or in jail. Plus there's a snowball's chance in hell that Cynthia will be into him, so that fifty bucks is as good as his.

"Alright." He finally shakes Cisco's hand. "Deal."

Cisco pumps his fist in the air. "Yes!" He gets up abruptly. "Alright, I will see you at 6:30 AM sharp on Monday."

"What? 6:30? Cisco!"

But he's already running off in the direction Cynthia was walking earlier. Barry sinks into his seat and sighs. Caitlin smiles coyly.

"The beach trip?"

He nods. "He thinks she'll be super into him because of 'the vibe' or whatever but apparently I'm somehow necessary to his plan."

"Keep me updated. I'm curious just how poorly thing are going to go."

"You could always come." She gives him an incredulous look. "I mean, it would be nice to have some company."

"You'll have Cisco."

Barry laughs dryly. "You know how he gets. The only time he's gonna talk to me is when he needs me to kiss his ass. I'm gonna be on my own whenever he's following Cynthia around."

"Good point."

"So you'll come then?"

"I have college essays to write."

Barry rolls his eyes.

"You can do that when you get back. They're not gonna run away or anything." She smirks. "And don't you wanna be there for 'the greatest week of Cisco's life?'"

"It would certainly be an interesting viewing experience."

"That's the spirit."

She looks at him quizzically.

"Why are you trying so hard to convince me? You don't even want to go."

"You're good company," he says. "It would make it a little more bearable to have you there."

"Only a little?"

He grins.

"Maybe a tiny bit."

They sit in easy silence for a few moments.

"So will I see you at 6:30 AM sharp in Cisco's driveway on Monday?"

She flips a page in her textbook, the shy smile returning to her face.

"We'll see."