A/N: Just a quick note before you start reading, this story is set in Canada, so the legal drinking age is 19 and the university system is probably a bit different than the States.

Prologue

"Take me away, A secret place, A sweet escape, Take me away,

Take me away, To better days, Take me away, A hiding place…"

Castiel lay back on his bed, humming along to the music blaring from his headphones, eyes closed, his air conditioner blowing cool air in a soft, almost pouring stream. While he generally despised repetitive songs, this was a guilty pleasure – a form of therapy that he desperately needed seeing how the past week had gone by. Now was the time to relax, to de-stress and he planned on doing just that. Of course, he knew that most likely wasn't going to happen for long when he factored his family into the situation.

And with that thought, Michael burst in through his room's door, with Gabriel hot on his heels. Before Castiel knew it, his headphones were snatched out of his phone and ears.

He sighed and sat up. "Yes?"

"This room is glacial." Michael said. "Aren't you cold?"

Castiel shrugged and Gabriel rolled his eyes. "We're going out."

Nodding, Castiel replied, trying to avoid the inevitable. "You have my permission."

Gabriel smirked. "You're coming with us."

He groaned. "I just came back from my last exam!"

"Exactly. Look, it'll just be us, Jo and Dean," Michael answered. "You have the rest of the summer to do whatever."

Castiel was relieved to hear it wasn't a party. Now, Castiel wasn't anti-social, or a party-hater. It was more so the kind of parties that Michael and Gabriel liked to frequent. "I'll come."

Gabriel clapped and snickered. "I told you mentioning Dean would work."

Michael shook his head with a slight smile as Gabriel sauntered out, then followed him with a 'we'll be waiting downstairs', leaving a sputtering Castiel to get ready.

ooo

Castiel fingered the collar of his navy and grey plaid button-up. Plaid because he knew Dean liked plaid. He didn't know Dean very well, however. Aside from a serious nod, or a joke made between him and Michael or Gabriel, Castiel didn't really hear much from him. After all, Dean was Michael and Jo's friend, and Castiel was the youngest in the group. Not to mention he had just barely graduated high school now that exams were over and those three were all going into their second years of university. He hadn't had many chances to interact with Dean - despite how much he wanted to do so.

As the Novak car pulled into the parking lot that separated Castiel's highschool from a baseball diamond and bleachers, his eyes searched for the black Impala that exuded the same air of untouchability as it's owner. Dean and Jo were in front of the car, and Jo talked animatedly, Dean nodding along, a beer in hand, but as the Novaks stepped out of their car, Jo ran over hugging them all.

Castiel always felt at ease around Jo - she was one of those friendly people you felt you could trust even without really knowing them. He hugged her back, and as they separated, she turned him towards the bleachers. "So, have you decided where you're going to go this fall?"

"No…" Castiel craned his head over his shoulder to see if Dean and his brothers were following. "Not really… I'm trying to decide between my top two – Queen's and McGill."

"Oh wow! What are you going for?" Jo asked, as they climbed their way to the top of the bleachers. Sitting down, he answered, "A double major in Philosophy and Psychology."

As he says this, Dean, Michael and Gabriel make it to the bench. Jo nodded slightly. "That's a lot of work, huh?"

Gabriel rolled his eyes, breaking into the conversation, "And Law school after that! Cassie here is a bit of an overachiever."

Castiel grimaced slightly and looked down at the hem of his shirt and muttered, "Don't call me that."

"Law school, huh?" Dean voice seemed to run through Castiel like a shock.

Castiel's head shot up and he nodded slightly in Dean's direction, meeting sage green eyes that caught the sun in ways Castiel never would have imagined eyes could.

"Sam wants to go to Law School too. What kind of Law?" Dean asked.

"Oh, I… um… not sure. Not corporate. Maybe criminal law, you know, prosecution? Or civil law, probably in human rights? I have 4 years to decide." Castiel replied.

"True, true." Dean responded, taking another swig of beer. "Speaking of universities… Seeing as you're all here, I'll just break the news. I, uh, dropped out."

"What?" Jo gasped. "Why?"

Simultaneously, Michael and Gabriel said, "Woah…"

"What about your Dad?" Michael added.

"That's the thing… Dad and what he wants - I can't do it anymore. The whole studying like crazy and doing a 9 to 5? Doesn't cut it. And I'm not like Sammy. I can't put in all those extra years just for money like he would. I only went because… I gotta do my own thing now." Dean shrugged, chugging down the rest of the beer.

Jo patted Dean's knee. "Whatever you feel is best, Dean. But... what are you going to do?"

Dean shrugs again, and that's what does Castiel in. How does someone not have a plan for two months down the road? Aside from the small blip of what path of law he wanted to take, Castiel had his whole life planned out, when to get married by, when he wanted children, when he'd start his own firm, his retirement plan of becoming a professor… And yet, there were people like Dean, who just dropped out of university and shrugged. Shrugged!

"How do you not know?" Castiel blurted incredulously.

Dean looked at him for a moment, then answered slowly, almost cautiously. "You never know what life is going to throw at you anyway. I figure; might as well go with the flow."

Castiel bit the inside of his cheek. He was thinking. He thought hard for the rest of the time on the bleachers while the others chatted. When it came time to leave, he absentmindedly hugged Jo, and as he came to shake hands with Dean and their gazes met, Castiel realized he had never been more perplexed by anyone in his whole life. And he wanted to know more.

A/N: So, this is my first Supernatural fanfiction! I'm really excited to be writing it and I hope you liked reading it so far :) I'm on break so the first chapter might even be posted later today - thanks for reading!

- city-of-wonder

PS. The lyrics at the start are from the song Pocket Full of Sunshine by Natasha Bedingfield and do not belong to me in anyway, and same goes for SPN and the characters from the show :)