Sam- 14

Dean- 23

-0-0-0-

It all started with Dean. Honestly, when had it ever not start with Dean? Anyway, when Dean heard from Brady that Sam was going on a date with some chick named Nichole later that night, he knew what he had to do. It was his job—as Sam's big brother—to make sure that the date went off without a hitch...right? Right, Dean justified in his mind, I mean, which sibling doesn't spy on their sibling's first date.

Dean knew in the back of his head that literally no one does that but he's protective...sue him. Now, Dean doesn't actually know where this date is but being a detective had its perks. Thank god, he was able to tap Sam's phone to listen in where they were going.

Once Dean knew where the date was taking place, he decided that it was about time to enlist some troops as backup. Stakeout's were never fun alone. Who, you may ask, is crazy enough to spy on Sam and spend a couple hours with Dean? There is only one person mad enough, his partner in crime, detective Castiel.

"Hey Cas..." Dean grinned, sliding up next to Castiel at the precinct

Castiel glanced up at the older Winchester brother, then frowned "No." He started to walk away.

Dean's face dropped "But Cass..." He whined, following Castiel. "You didn't even know what I was going to say yet!"

"Exactly, when you get that look on your face nothing ever ends well. The last time you gave me that grin, we ended up in a cage with King Kong."

"Pshh...you've always been too dramatic for your own good. Besides, this time there are no animals involved. I swear." Dean put his left hand on his chest and held his other hand up "Scout's honour."

"Dean, Sam told me you did boy scout's for one week." Castiel scoffed. "I don't think that counts."

"Please." Dean begged "I really need your help."

"Fine," Castiel sighed "What mess have you gotten yourself into now."

"Well-."

"And make it quick. I've got to brief Captain Winchester on a case." Castiel was referring to Sam and Dean's grandfather, Samuel Winchester-Sammy's namesake. Grandpa Winchester was the man behind the desk, in charge of the NYPD.

"Do you mind helping me spy on Sam and Nichole's first date?" Dean smiled as if his request wasn't basically asking him to stalk someone with him.

"And what exactly does this entail?" Castiel asked, not believing that he was even considering Dean's proposal.

Dean beamed "So, I tapped Sam's phone and-"

"How did you-"

"Not important. Anyways, Sam is taking Nichole to the movie theatre at 7 to watch what I hope is not a chick flick. So, I bought us two tickets and we're going to sit behind the two love birds, and observe. Kind of like a stakeout."

Castiel took one look at him and sighed, "I can't believe I'm doing this."

Dean clapped Castiel on the back "Thanks man, you won't regret it."

"Yeah, yeah." Castiel rolled his eyes "I expect an extra-large bag of popcorn and a coke when I arrive." He knew that he would probably regret it in the end, but who could say no to Dean Winchester when he has that hopeful look on his face. Saying no would be like kicking a puppy.

And that, is how Dean Winchester convinced his best friend and detective partner into spying on his brother Sam and his girlfriend.

Still, when the clock striked seven, Castiel found himself checking his watch for the fifth time in the last minute. Castiel sighed to himself, Dean was six minutes late. He tolerated many things like Dean's crazy ideas that usually got them into trouble, but tardiness was not one of them.

"Sorry i'm late Cass." A voice panted behind him, out of breath.

"It's fine Dean just try t- by the angel. What in the world are you wearing?"

Dean looked at his clothes in confusion at Castiel's exasperated tone. He was wearing a pair of black sweatpants, a black jumper and black and white converse "What's wrong with what I'm wearing?"

Castiel looked at Dean incredulously "You're joking, right? Dean, you look like you're going to rob a bank."

"This is my disguise." Dean muttered defensively, dragging Castiel into the theatre.

"There they are." Dean pointed to somewhere in the crowd, then proceeded to drag his partner into two rows behind the two lovebirds.

Castiel sighed, "I still can't believe I'm doing this."

Dean grinned devilishly, holding up a box of m&m's. "Want one?"

"Thanks, but i'm all set." Castiel held up his bag of popcorn. "Remind me again why we are sitting in the middle of a movie theatre, watching a movie geared towards teen's, not 23 year old men."

"Look alive Cass. It's my job as a big brother to make sure Sam doesn't choke and to observe possible suitors." Dean shrugged. "I have to see if she's Sam's Juliet."

"Juliet?" Castiel raised an eyebrow "I didn't know you could read, let alone know where the library is."

"Anyway," Dean muttered, blushing in embarrassment, "they're talking and I'm trying to listen!"

Castiel scoffed, pulling out a device from his pocket, along with ear buds "No need. I bugged the place before you arrived."

Dean smirked slightly "Committed."

Castiel mirrors Dean's smirk, "You should know by now that I never do anything half way."

"How did you know where Sam was going to sit?" Dean asked.

"A magician never reveals his secrets."

He flipped on the device and moments later they could hear exactly what was happening between the two.

"Do you want a gummy bear or starburst?" Sam asks, holding out the two box's.

"Uh, whatever is good. Doesn't matter, not at all," Nichole laughed nervously.

Sam smiled sheepishly and nods, "Sounds good."

Sam awkwardly tried to place his elbow on the arm rest Nichole's arm was already on without touching her. Dean can't help but snicker at his brother's awkwardness.

"Hey." Nichole nugged Sam with her elbow "Are you alright?"

Sam sighed, "I-I'm really sorry, though. I've just...never done this before."

"Sam," Nichole shook her head, laughing, "just relax. Loosen up, it's fine."

"Yeah, you're right," Sam laughed nervously, fumbling with the corner of the popcorn bag. "You're right. Totally fine...right."

Nichole raised an eyebrow, chuckling slightly "If it's any consultation, I think it's cute."

The two detectives stare, their gazes jumping to and from where they can see Sam and Nichole and the device they're using to listen to the bug.

Dean looked at Castiel, a shit eating grin on his face "I knew Sam was awkward, but who knew a simple crush could turn the normally unflappable Sam Winchester into such a flustered mess?"

"You are crazy," Castiel paused. "No, I'm crazy for getting roped into this."

The rest of the date went on as any other would. They watch the movie in silence, then afterwards they decide to take a stroll in the park, where Dean and Castiel hid in a bush and facetimed Jessica and Brady, who wanted to watch as well. In the park they get to know each other better and those spying on them learn that Nichole was definitely trustworthy enough. Although Dean knows that they made a cute couple, it probably wouldn't last. High school relationships rarely did.

Eventually, Sam flagged down a cab for the two of them. Just before they enter the vehicle, though, Sam took a deep breath and leaned in. Sam kissed Nichole who kissed him back.

Castiel sighed dreamily "Call me a hopeless romantic, but this is adorable."

Dean popped out of the bush, shouting "Get some Sam."

Sam jumped back in surprise when he heard the familiar voice. "Dean?"

Castiel pulled on the end of Dean's pant leg and screamed quietly, "You idiot!"

Dean winced, "Sorry?"

Sam glared daggers at Dean "What the hell man?"

Dean laughed, not fazed by Sam's glare "Who knew Sammy had guts because he definitely doesn't have game."

Sam stalked over to the bush, expecting to see only his brother. Imagine his surprise when he not only found Dean. but Castiel face timing Jessica and Brady.

"What the hell Castiel? You too?"

Castiel stood up, next to Dean "Against my better judgement."

Sam turned to the phone "And you two. Do you have anything to say for yourself?"

Jessica and Brady stared at Sam, looking like they'd seen the devil.

"Uh, I think I hear my mom calling me. Coming mom!" Before Sam could protest Jessica and Brady had hung up.

"Dean." Sam took a deep breath "What are you doing here?"

"Uh, ummm..." Dean whipped his head around to Castiel, begging for help.

Luckily, he was interrupted by Nichole "Wait? Dean? As in your brother Dean?"

"The one and only." Sam glared at Dean.

"What are you doing here dude!" Sam shouted at Dean.

"Well Sammy." Dean rubbed the back of his neck sheepishly "I was just being a good big brother. Spying on your first date to make sure everything went smoothly."

Sam turned to Castiel who just shrugged "I think he was just bored."

"Cass." Dean hissed

Nichole shook her head "You've got yourself one crazy family Sam."

"Don't I know it." Sam muttered, but there was a hidden smile peeking out from his frown.

"So, did I meet your standards, Dean?" Nichole leaned against Sam who shifted to pull her closer.

"Well..." Dean pondered "Personality I think your totally out of Sam's league."

"Dean!" Sam exclaimed, horrified.

"It's like a cliche high school movie." Dean continues "Except it's the nerdy guy who goes out with the pretty cheerleader."

Castiel agreed "But you are a very cute couple."

"Thanks." Sam blushed "This doesn't mean I've forgotten about the fact that you four were spying on me,"

Dean's grin grew "You'll thank me later."

"We will continue this conversation later Dean. You can tell Jessica and Brady the same thing." Castiel let out a sigh of relief "And don't think that I've forgotten about you Castiel." Sam warned before linking his arm with Nichole's "C'mon , Nikki. We're still not quite done our date yet."

"Definitely not, Sam," Nichole placed a kiss onto Sam's right cheek causing Sam to blush for the umpteenth time that night.

With that, Sam opened the door to the taxi, helping Nichole into the car before getting in himself.

It's only after their car has driven off that the two detectives could finally relax.

Dean smiled at Castiel "Well. I think that went well." He looked down at his watch, realising the time "I should be going now. I'll see you tomorrow."

Dean turned with a wave and began to walk away but Castiel stops him with a hand on his arm.

"This was Sam's first official date." Castiel stated, turning Dean around.

"Uh," Dean's forehead scrunched up, "I guess?"

"Well," he paused, wondering if he was making the right move, before continuing with a more resolved tone, "when's ours then?"

Dean froze, "Uh...wait, really?"

Castiel searched Dean's eyes, wondering if he should continue.

Finally, he nodded to himself, smirking "Tomorrow. I'll pick you up for breakfast at 6 before we have to be at the station."

Not knowing what else to do, Dean simply nodded vigorously, still in shock.

"Great," Castiel grinned and walked away, heading to his car "I'll see you tomorrow, partner."

"Huh," Dean mumbled to himself, "well who would've guessed."