Gabriel was easily considered the most immature archangel of all time. Michael and Raphael sometimes wished it had been Gabe that had been thrown in a cage- at least Lucifer could act dignified when he had to.

But Gabriel didn't care about being dignified. He wanted to have fun! And most of the angels in heaven were entirely against the notion of fun.

But Gabriel was positive that some of his brothers and sisters weren't strict, and he eventually found them all. The small pack of fun angels he created consisted of Balthazar, Castiel, Anna, Hannah, and Samandriel. Their small group was determined to have as much fun as they could in heaven.

And that was the reason why the rest of the angels forbade the entire group from ever going to Earth, where the humans lived. Especially after a prank had gone wrong, and Anna had been cast out, falling.

While Gabriel deeply regretted what had happened with Anna, it didn't stop him from having fun with his siblings. It just meant that he'd check on Earth every now and then, just to make sure Anna Milton was doing okay. He had shown Castiel how to watch the humans one day, and his innocent little brother had quickly become obsessed.

Which brings up to now, with Gabriel and Balthazar wrestling around as Castiel stared intently down at the humans.

"Come on, Cassie!" Gabriel called out, grinning. "I need a challenge!"

"Oh please, I'm letting you win!" Balthazar declared. Gabriel pinned him to the floor, smirking.

"Oh really?" Balthazar scowled and shoved at him. "Come on, Cassie, why won't you PLAY WITH US??" Gabe whined. Castiel shook his head.

"I'm busy, Gabe." The archangel walked over, glancing down at the earth.

"Who are you watching?" He asked. Castiel smiled, and pointed down at a young man with green eyes. 

"Dean Winchester." He offered, trying not to blush. Gabriel eyed the human carefully, his smirk growing.

"Not bad, Cassie." He paused, remembering the name Winchester from somewhere. "Wait....isn't that Michael's sword?"

"Nope." Castiel announced. "This one's mine."

"But Dad-"

"MINE." Castiel repeated.

"And what if Michael demands him back?"

"Then.....What's that thing you said the humans say?"

"What? Go suck a dick?"

"Yeah. Then Michael can go suck a dick, because Dean Winchester is MINE." Gabriel laughed.

"Aww, little Cassie has a crush!" Castiel looked up, alarmed.

"I do not!" He exclaimed. "We're not allowed to have crushes on the humans, because being with the humans is forbidden and if you are, then you might create a Nephilim , and then-"

"Cassie." Gabriel deadpanned. Castiel paused, glancing at his brother. "If you want to have a crush on Dean Winchester, then go right ahead."

"But-"

"No buts. Besides, in order to have a relationship with him, you have to be on earth, right? There's nothing stopping you from loving him from afar." Castiel sighed, gazing back down at the human.

"But if I fall in love with him up here, then I'll HAVE to meet him down there."

"So, then..... Possess a guy when you go to Earth." Gabe suggested. "That way you can't make a Nephilim." 

"....You are strangely intelligent, Gabe."

"I know. It's a gift."They looked back down at Dean Winchester, watching as he started to talk with another human, one with much longer hair.

"Who's that?" Gabriel asked, his eyes lingering on the tall, handsome human.

"That's Sam. He's Dean's younger brother." Castiel explained.

"Oh."

"He's one of the children infected with demon blood."

"Oh." Gabriel barely heard anything Castiel said after that, as he stared at the beauty that was Sam Winchester.

Castiel's fixation with Dean Winchester never stopped, and Gabriel found himself drawn more and more towards the pair of brothers- and specifically to Sam. Finally, he just couldn't take it anymore.

He HAD to see them in person. Just to get himself to snap out it, and stay away from Sam. And to make sure that Dean was worthy of Castiel, of course. 

"Balthazar, I need a hand." He declare one day.

"I'm in." Balthazar instantly agreed. Gabriel, in his opinion, was the only thing keeping heaven interesting.

"I need you to help me break out of heaven so I can visit the humans." Balthazar froze.

"But....Gabriel.." He insisted. "That's impossible. Last time we tried-"

"Anna, I know." Gabriel admitted. "But it IS possible, and I just need you to keep Michael and Raphael and everyone else out of my way so I can make a break for it."

"But why do you have to see the humans anyway?" Balthazar questioned. Gabe smirked.

"Well, SOMEBODY'S gotta see what Cassie's boyfriend is really like." He offered.

So Balthazar held watch, and Gabriel made his way to the doors of Heaven, spotting Hannah guarding them of course.

"You can't." Hannah told him. "It's forbidden!"

"Hannah, please." He proclaimed. "After everything I've done for you- can't you just let this one thing slide?"  Hannah hesitated.

"You really haven't done much for me."

"I'll be RIGHT BACK, I swear!"

"Uh huh. And how long is right back?"

"Uh....It's Monday, right?" Gabe offered. "I'll be back by Wednesday morning. Promise." Hannah sighed.

"Just this once." She declared, shutting her eyes. "Go."

"You're the best sister ever." He darted out, and as soon as he found a vessel, Gabriel headed for the Winchesters.

The Mystery Spot. Castiel nearly laughed at the name. But Dean seemed interested in exploring the attraction, and Castiel was content to watch as he and Sam solved another case. Just like normal.

But then Dean got shot and died.

And Castiel screamed, ready to panic-

And then, all of a sudden, Sam Winchester woke up. Dean was fine. The day had started over.

Castiel froze. This never happened. He watched closely, whimpering every time Dean died and Sam would wake up. Over a hundred times it happened, until finally Sam figured it out, and had a stake to the Trickster's neck.

Castiel let out an angry gasp.

"Gabriel!" He hissed, infuriated that the archangel was the one who had been killing off his crush hundreds of times. 

****

"So, how was Earth?" Hannah asked as Gabriel walked back into heaven.

"Wonderful. Do you know how AWESOME candy is?" Gabe insisted, but his peaceful return was quickly interrupted.

"GABRIEL!!!!" Castiel yelled out.

"Uh oh." For a tiny angel, Castiel could sure pack a punch; a fact that was quickly proved as Castiel tackled his brother to the ground and started wailing on him.

"HOW DARE YOU HURT MY DEAN!?!?" He yelled out angrily.

"Cassie wait! I can explain!" Gabriel insisted. Castiel glared at him, but paused. "Okay, YES, I killed your boyfriend. The first three times it was ENTIRELY intentional. But I just wanted to make sure that he was good enough for you!"

"And the other hundred times?" Castiel demanded. Gabriel stared at the ground.

"Well.... those were just because I wanted to see Sam." He admitted. "I promised Hannah I'd be back by Wednesday, and- a day is just too short, Cassie! Imagine if, after so many years of watching him, you only got twenty-fours hours with Dean! That's ridiculous! So killing Dean was the only way I could spend more time with him!"

Castiel paused, imagining it.

"You love Sam." He concluded. Gabriel stared at the ground and nodded.

"And you love Dean." He replied. Castiel nodded.

The archangel sighed.

"What are we gonna do, Cassie?" He wondered out loud.

"One day," Castiel began. "One day I'll meet Dean in person, and I'll make sure you're allowed on earth too. And then we can both be with the Winchesters we love." Gabriel smiled.

"That'd be nice, Cassie." 

"We can make it happen." Castiel declared. "We're angels, aren't we?"