The demanding life of a teenager [Destiel AU]

A little brotherly advice

"Well played today, squirrel!" Crowley announced as he got out of the Impala. 

"Thanks, you too", Dean replied. "See you at Monday."

Crowley nodded and walked towards his front door as Dean started driving away from his house. Was really this guy's friendship worth more than Cas'? Dean wasn't so sure. Crowley had seemed like a pretty cool guy in the beginning, but Dean had started finding him quite annoying after a while. Like all his nicknames. Squirrel? Seriously? Dean did not look like a squirrel! Besides, Cas seemed like a really nice guy and Dean could understand him getting hurt when he didn't stand up for him. Especially after Dean literally chose Crowley over him.

Dean had no idea what to do. He had a feeling that Cas would give him another chance if he changed his mind. If he then found out that he didn't get along with Cas, however, he doubted that Crowley would take him back. Dean rubbed his forehead with his palm. He could go crazy thinking about this all day.

As he parked in front of his house, Dean decided to push his dilemma aside for a little while. It was Friday. He had an entire weekend to relax before having to make a decision. Maybe even Sam could help him out. Sam had always been better at these situations than his bigger brother had. As Dean got out of the Impala and walked towards his house, he decided to ask his brother before doing anything else.

He was just about to open the front door when it went up, a blonde girl stepping out. He looked questioningly at Sam, who stood right behind her. Sam rarely had girls over.

"Oh, hey Dean! This is my friend Jessica from school", Sam explained. "Jess, this is my brother. Dean."

"It's so nice to meet you, Dean", Jessica exclaimed as they shook hands. "Sam has told me all about you."

"Nice to finally meet you too", Dean said as he grinned at Sam, who narrowed his eyes. So this was Jessica. She was pretty. Way out of Sam's league. Her blond hair was long and she had sparkling, blue eyes.

"Well, I have to go", Jessica announced after a short, awkward silence. "See you, Sam!"

The boys said goodbye before walking into the house, shutting the door behind them.

"She's hot", Dean remarked, winking at Sam.

"Shut up", Sam mumbled. He quickly turned around to wander off to his room, but Dean could already see a blush creep up his neck.

"You like her, don't you?" Dean pressed as he followed his brother. Sam just kept on walking. "I could help you, if you want?" Dean offered when Sam still didn’t respond. This finally caught his attention though, and he turned around.

"Help me?" He asked suspiciously.

"Yeah, help you getting her interested in you. All I want is a small favour in return."

Sam narrowed his eyes again. "What do you want?"

"I have these two friends who don’t get along, and they're making me choose between them. Honestly, I have no idea which one to choose." 

"Don't choose either of them", Sam shrugged. "Now, what should I do about Jess?"

"I'm serious, Sam", Dean warned him.

"Ok, just tell me everything that has happened", Sam sighed. "But afterwards, you'll help me with Jess. Promise?"

***

"And then he tells me to leave him alone, and just walks away!"

The brothers had sat down at the kitchen table as Dean told Sam about everything that had happened between him, Cas and Crowley over the past few weeks. As he waited for his brother's answer, Dean finished his pie, shoving it all in his mouth at once.