Sam
He hasn't felt right since the morgue.
Sitting in a crowded restaurant, surrounded by couples and cheesy heart shaped decor with his brother, their resident angel, and their friend returned from hell (and the current object of his brother's pining), is doing nothing to settle the prickling paranoia and restlessness that's been infecting him all day.
Sam stabs at his salad aggressively, trying to distract himself from the cravings he's been having on and off for the last few hours, listening to Anna and Cas argue over the cupid.
"It's a godsdamned cherub, we should call it that. E- Cupid," Anna hissed the word cupid furtively, glancing around like the name was going to summon a wing child in a diaper, "is something else, something extremely dangerous, and we should not be throwing his name around like that." Sam exchanged a worried look with his brother. Anna has been a little extra paranoid recently, but being afraid of a name is a little much. It looks like she's backsliding again, which only reinforces to Sam that it's time to call in some reinforcements to help her. He and Dean are completely incapable of creating an environment that invites mental stability. Hell, the two of them are the exact opposite of positive examples for positive mental health.
"It does not matter." Cas waves off her concern, even as Anna's expression grows more murderous. "What matters is that our target is likely to show up here. This place will be a fertile garden for a rouge cherub to pollinate." Cas trails off as he watches Dean slather his burger in ketchup. Anna is picking disinterestedly at her salmon.
"Why the hell would a cherub go rouge in the first place?" Anna asked, flicking a stray piece of fallen heart confetti out of her untouched food. Sam does his best not to frown at that. The only substantial thing Anna had consumed in the last two days was the bottle of Ensure Sam insisted she drink. Even though she's been recovering relatively steadily physically, that will only continue if she eats enough. And when she gets bad, she usually doesn't.
"I- I am... sorry, are you going to finish that?" The angel is practically salivating over Dean's burger, which is odd considering that Cas is always completely uninterested in human things like food and drink.
"No. All yours Cas." Sam's head snaps up to stare at his brother. Anna's also looking mildly concerned as they watch Dean pass his plate over to Cas.
"Wait a minute, you're not hungry?" Dean just shakes his head, and looks around the crowded restaurant. Anna silently pushes her plate away too, having only taken a few more bites of her dinner than Dean. Sam takes a slow bite off his plate as he watches Dean stare worriedly at Anna while she visibly sweeps the restaurant.
Suddenly Anna and Cas both stiffen.
"He's here." The two of them announce, eerily in synch. Sam scans the restaurant.
"Where? I don't see anything." Beyond a weird draft in the tacky decorations, nothing in the dimly lit restaurant has changed.
"He's hidden. But look there." Anna nods towards a couple giggling together at their table.
"Same side of the booth couple over there?" Dean asks skeptically.
"Yes." Cas stand abruptly, absently cleaning his fingers on a napkin.
"Meet me in the back." The angel stiffly wanders away. Sam turns to his brother and Anna, the latter of whom is practically shaking with the need to follow after Cas and the rogue cupid. Sam sighed.
"I'll flag down the waitress, get this food all packed up for later. I'll catch up with you guys." He doesn't want their dinner to go to waste. Especially since two of their party haven't eaten anything, and Anna has hardly eaten at all in the last twelve hours.
It only takes him a few minutes to settle their tab and rush to the back of the restaurant carrying all the take out boxes. And yet somehow he still manages to miss most of the action. Instead of something that even remotely qualifies as normal, considering their brand of weird, Anna is holding a naked man standing at sword point as he sobs. Both Dean and Cas are staring at the scene with wide eyes. Dean even has one hand stretched towards Anna uselessly, a half thought through action left incomplete.
"All we need to know is why." Anna demanded tersely. The naked man's eyes were flooded with tears that poured over soft rounded cheeks.
"I- I don't know what to say." His voice wavered and cracked before he turned away from the group, a hand pressed over his eyes as he sobbed. Sam sidled up to Anna, take out boxes pressing uncomfortably against his leg through the plastic bag.
"Uhh, what the hell is happening?" She shrugged, not taking her eyes off the sobbing man. Sam knows her well enough to recognize the mostly empty threat of her sword - although how she keeps getting it back and bringing it with her without them noticing is beyond him. Of course with Anna, no threat is truly empty, since she can flip from relaxed to battle ready almost as quickly as Cas can.
"I have no clue. We started interrogating the cherub and now he's crying." Sam glanced back at the crying man- or angel as the case seemed to be.
"Wait, that's the cherub?" Anna shrugged again. She stepped closer to the angel, slowly lowering her sword, but not putting it away yet.
"Yup." Cas seemed to have lost some kind of argument with Dean and he slowly approached the sobbing cherub.
"Look, we didn't mean to hurt your feeli-" Cas squawked as the cherub suddenly turned around and crushed him into a naked hug.
"Love is more than just a word to me, you know? I really love, love. I love it! And if that's wrong then I don't want to be right." He insisted in a rush.
"What the fuck?" Anna whispered under her breath.
"Yes, of course" Cas patted the calmed cherub awkwardly on the back, "I have no idea what you're saying." The cherub pulled away, gripping Cas by his shoulders so he could look at the other angel in the eye.
"I was just on my appointed rounds! What, whatever my targets do after that, that has nothing to do with me. I was just following orders!" Anna rolled her eyes and sheathed her sword.
"Obviously. You're not capable of doing anything else. But who ordered you after those targets specifically? Did they come in differently than usual? Did you get new orders from someone else? Where the orders late or early or-" The cherub looked disgusted, cutting off Anna's interrogation.
"Of course not! I got my orders the same way I always have, from Heaven. And I am very good at following them thank you very much." He turned to Cas. "Please Brother, read my mind. Read my mind and you'll see." Cas looked faintly disgusted as he nodded his head in agreement. What followed was possibly the most uncomfortable staring contest Sam had ever been forced to watch.
"He's telling the truth." Cas confirmed, taking a large step out of the other angel's arm span.
"Jiminy Christmas, thank you." The cherub was visibly relieved, no sign of tears left on his round face.
"Wait, why does Heaven care if Harry meets Sally?" Dean demanded. Anna rolled her eyes at the question. Sam tried to look uninterested, like he also already knew the answer. But also he really wanted to know.
"Well mostly they don't." The cherub shrugged, "but you know, certain bloodlines, certain destinies. Oh, like yours." He adds, looking pleased twiddling his thumbs.
Oh. Cain and Abel. Micheal and Lucifer. And now, Dean and Sam. Shit, Dean isn't going to like this.
"What?" Dean blurts out.
"Oh yeah, the union of John and Mary Winchester, very big deal upstairs. Top priority arrangement." The cherub hummed, bouncing on his toes.
"You're saying, you fixed up our parents?"
"Well, not me but yeah. It wasn't easy either. Ooh, they couldn't stand each other at first. But when we were done with them, perfect couple!" Sam wanted to punch the wide grin off the cherub's face. Since their parents had been pushed together by the machinations of a cupid, it's no wonder Dad had gone completely off the rails when Mom died. They weren't just in love, they were obsessed. Just like all the couples whose love, no- obsession, had been twisted into killing each other.
"Perfect?" Dean demanded.
"Yeah!"
"They're dead. And so are a bunch of other people."
"I- I'm sorry, but the orders were very clear. You and Sam needed to be born. Your parents were just uh, made to be." The cherub started singing, completely oblivious to the increasingly dark look on Dean's face.
Dean reeled back and did what Sam has been wanting to do pretty much since he walked into the naked cupid interrogation and punched the grinning angel straight in the mouth.
"OW." Dean clutched his fist to his chest as the cupid vanished.
"Hey!" Anna shouted, lunging towards the empty space before coming up empty.
"Where did he go?" Dean demanded, twisting back around again.
"Gone." Anna hissed disappointedly, glaring at the concrete.
"I believe you upset him." Cas points out mildly.
"Upset him?"
"Dean, enough." Sam jerks his head towards Anna who was starting shake as their voices got louder. He sidled closer to his brother, intentionally keeping his voice low. "Look, we gotta talk about what's going on with you, ok?" Something's been eating at Dean for days, ever since they got back from 1978. Even discounting his caginess with Anna, and how much she's been changing his brother, the last few days have still been extremely weird by Dean standards.
"No. We don't." Dean storms off, roughly shouldering past Cas, and nearly ignoring Anna's gentle attempt to grab onto him.
"Dean." His brother stops to look at her for a long moment. Anna's hand wrapped around his forearm, not really holding him in place so much as asking Dean not to stomp away. Sam felt a breeze rush around the room, and he would almost swear he heard a low laugh somewhere behind him. After a long pause Dean sighed, his shoulders caving in towards himself.
"I'll see you guys later." Anna's lips thinned but she said nothing else, letting go, as Dean walked away. Sam took several deep calming breaths.
"Ok. Time to regroup. If it's not cupid-"
"Cherub." Anna insisted vehemently. She'd started to shake, her whole body trembling. Sam held back a sigh, and just wrapped an arm around her shoulders. He shot a meaningful glance at Cas, and the angel just stared balefully back at him. This time Sam did let out a sigh, did he have to do everything? He carefully pried the sheathed sword out of Anna's hand, and started walking them out towards the parking lot.
"Fine, it's not the cherub. We're back to square one. What the hell is causing all these deaths?"