A/N: I don't know why I called this book something as generic as Destiel oneshots when a lot of these are just general Supernatural oneshots in a realm where Destiel exists, but anyway here's a oneshot about Jo and Dean and Cas because I've been sitting on this cringey idea for awhile so fudge it

Jo Harvelle and Dean Winchester were best friends. Had been since birth, all the way up to now in high school.

And not like BFF best friends; like 'we are literally siblings in every way but blood and I will die or kill for you the second you ask' best friends. Brothers from another mother, except that Jo was a girl, and Mary Winchester sucked.

And that meant that whenever one of them had a problem, the other dropped everything to help. Jo had done that recently for Dean, when he had needed help getting a date with Cas Novak, so now it was Dean's turn to do a favor for her, and unfortunately, she needed a big one at the moment.

Jo was laying on her bed having an internal, and nearly external, crisis. She was late. How could she have been SO STUPID? She figured it was just her luck. You spend one night with Ash and end up paying for it for the rest of your life. And granted, she hadn't been ENTIRELY stupid. She was on birth control. Was it really her fault that Ash hadn't held up his side, and that those stupid pills didn't always work?

But she also wasn't sure. Being late wasn't always a death sentence. Sometimes it was just nature freaking out. But she had to check.

But telling Ellen Harvelle you needed to borrow the car to go buy a pregnancy test was not something you did and lived to tell the tale of. So Jo did the only thing she could. She called Dean.

"Sup Harvelle?" The handsome teenager answered immediately.

"I need a favor." She began.

"Name it."

"I need you to buy something for me and bring it to me. I'll pay you back when you get here."

"Now?"

"Yes."

"Okay, what do you need?" Jo paused.

"....Don't freak out." She ordered.

"I won't freak out."

"Yes you will."

"Unless you're asking me to buy you some sort of drug- and I could get them if you needed it- I'm not going to freak out."

"I need you to buy me a pregnancy test." Silence. Dead silence. She couldn't even hear Dean breathing on the other end of the line.

"....I'll be right there." There was a click as Dean hung up the phone, and Jo buried her face in a pillow. Oh yeah. Dean was going to raise hell on her, likely in a way that would challenge Ellen's wrath.

****

Dean drove to the nearest pharmacy store, assuming that any place he bought condoms from would likely also have pregnancy tests. Didn't the two kind of go hand in hand?

Well, not true, he thought. If you used one, you weren't supposed to need the other.

He wandered the aisle, frowning at the thought. Jo was the most responsible person his age that he knew. How could she be irresponsible in this way, of all things? And if she was knocked up, then it would have to be with Ash's baby, which would only make minor poker night at Harvelle's bar more awkward. 

And speaking of Harvelle, Ellen would lose her fucking mind. Dean had no doubt about that. He was getting chills just thinking about it. But there was the possibility that this was a false alarm, but since he wasn't sure, Dean walked a bit quicker. He knew Jo had to be panicking, and desperate if she had asked him to bring her a test. The sooner they got this over with, the better for everyone involved.

And if it wasn't a false alarm and everyone else freaked the fuck out and ran away, well, then Dean had to be prepared for that too. Jo was his best friend. That mean the had to take care of her. It was what he did.

He found the aisle he needed, the 'aisle of life' as it was cornily named. It sold everything from the tests he was here for to adult diapers and everything in between. He stood in front of the section of tests and his frown deepened. Why did there have to be so many different brands for everything? Was there a difference? How was he supposed to know which one to get? Dean let out a sigh.

This is why I date boys, he thought.

Well, boy, currently. He had been out on four dates with Cas Novak so far, with plans for a fifth already. They had only kissed once, but Dean was determined to make the blue-eyed boy his boyfriend. Cas was just too awesome to let him get away, especially when all of their dates had gone perfectly so far.

He shook his head to clear his thoughts, focusing back on the tests. He couldn't think about Cas now. He had to focus on Jo.

But that became a bit more difficult when Cas came walking down the aisle, clad in a cheesy pharmacy uniform, fit with a little name tag and everything.

"Dean?" He asked, surprised. Dean jumped a mile and turned, rapidly scanning the aisle for anything, ANYTHING other then a pregnancy test that he could be buying- preferably something appropriate for a teenage boy to buy to but NOPE. The aisle was full of literally everything he COULD NOT BE BUYING, so OF COURSE CAS WAS THERE.

"hEY! CAS!" He said loudly and awkwardly, already breaking out into a nervous sweat as he attempted to look casual. His eyes settled on the name tag. "I didn't know you worked here."

"Yeah, my brother runs the pharmacy part, so he gave me a job in the rest of the store," Cas explained, eyeing him, slightly suspicious. "What are you doing here?"

"OH, you know," Dean waved it off. "Just....browsing....."

"Browsing." Cas deadpanned.

"Yes." Dean said seriously, his eyes wide.

"In a pharmacy store."

"Yes." He started sweating more.

"...You sure you're not here to buy something specific?" Cas asked.

"Yes. I mean NO. I MEAN YES. I mean-" Dean's tongue suddenly felt too large for his mouth. "I mean YES, I am here to buy something, that is what people do in stores." Cas stared at him for a moment, then broke into a slow smile.

"That is usually what stores are meant for, yes. Is there something I can help you find?" 

"No," Dean said quickly, his eyes darting around the aisle. "I think I can handle it."

"Are you sure?"

"Yes."

"Because you know you're standing in the aisle full of tampons, right?" Dean glanced to the other side of the aisle, his face going red at the sight of the feminine hygiene products.

"....Yes, I am well aware of that," Dean said seriously. "I..uh...." His brain fumbled for a response, a witty comeback of any kind. "I'm playing Truth or Dare with Jo and she dared to me to recreate that scene from Ten Inch Hero where the guy buys tampons for his girlfriend, and she told me to bring back the box as proof that I did it." Cas stared at him.

"Really."

"Yes." Dean stared back at him, silently prayed that he would buy the total lie.

"Are you sure you're not here to buy lube and condoms, because I'm not gonna judge you if you are." Dean's face went redder than a stop sign and he glanced towards the condoms, then back at Cas awkwardly.

They had barely kissed on their dates so far, and Dean certainly didn't have any plans to see anyone else. He didn't want Cas to assume he was sleeping around.

"I'm not," He insisted, and he leaned against the aisle and forced a smirk onto his face. "But if you want to get into my pants that bad, you'll have to buy me dinner first." Cas smirked and started laughing.

"I'll keep that in mind," He promised. "You're really not gonna tell me what you're buying?"

"....No." The nervous sweat returned in full force. Cas rolled his eyes.

"Well that's fine. I guess I'll just ask the cashier after you buy whatever mystery item you're looking for." Dean stared at him, terrified, and Cas stared right back, a devious look in his eye that told Dean he would definitely find out whatever it was he bought.

So Dean did the only thing he could think of.

He pointed down the aisle and yelled "LOOK!" and when Cas turned, he blindly grabbed a pregnancy test, shoved it down his pants, and when Cas turned back, annoyed, he slapped a handful of crumpled bills into Cas's hand. "Keep the change!" He declared and ran like hell.

"What- DEAN!" Cas called after him, but Dean didn't look back. He bolted out of the store, into his car, and sped down the street, swearing the whole time.

****

When Jo opened her bedroom door, a red faced, sweat soaked Dean Winchester burst into the room, slapped the test into her hand and promptly faceplanted onto her bed.

"I hate you so much right now," He groaned.

"Oh no, what happened?" She asked.

"CAS WORKS AT THE FUCKING PHARMACY."

"Oh shit," Jo swore. "Does he know-"

"NO, BUT IT WAS AWKWARD AS HELL."

"Did he see what you were buying?"

"GOD I HOPE NOT."

"Then what did he think you were doing there?" 

"I DON'T WANT TO KNOOOOWWWWW. I THINK I JUST FUCKED UP ALL MY CHANCE WITH HIM."

"Fuck, I'm sorry."

"You owe me fucking BIG TIME, HARVELLE. I had to cram the test down my pants when he wasn't looking and run for it." Jo started laughing. "IT'S NOT FUNNY."

"It is kinda funny." Dean sat up and glared at her.

"You better hope you're knocked up cause if you're not, I'm gonna kick your ass." Jo looked down and grinned.

"Well then I guess you'll have to kick my ass."

"What?"

"It was a false alarm." She said. She held up the boxed test. "So I don't actually need this anymore..." Dean stared at her.

"You mean to tell me I suffered for nothing?"

"Yes?" Dean gave her a look of death.

".....Start running."

"Understood."

****

It wasn't a total loss, Dean thought a few days later. After all, if he hadn't gone to the pharmacy, then Cas wouldn't have brought condoms as a joke on their next date. He bought him dinner first too.