AN: hey guys, thanks for waiting, and as promised, here is the next chapter~


The next few weeks had passed by rather quickly, everyone busy with getting Jake prepared for the life of hunting. Sam was in charge of homeschooling Jake, teaching him all there was to learn about monsters and how to kill them. Dean taught Jake the different kind of weapons and how to use them. In the end, Jake had settled with a machete, gaining an amused but approving look from the older hunter. When Jake was not busy having hunting information crammed into his head, he spent his time sketching on loose pieces of lined paper he found scattered around the library.

"Well, Damn, that's really good." Dean bent over Jake's shoulder as the teen was scribbling away on a half sheet of paper. The drawing was a detailed image of a deer, running through a forest. Jake didn't look up, simply grunting in response as he kept his head lowered to the library table, focused on shading in the picture. "Hey, c'mon kid, take a compliment," Dean said, patting Jake on the back.

"Sorry," Jake mumbled, still not looking up. Jake could practically hear Dean roll his eyes before walking away in defeat.

"What do you want for breakfast?" Dean asked from the kitchen, his voice almost muffled by the sounds of dishes banging together. Jake sighed and put down his pencil, finally lifting his head towards the direction of the kitchen. Thinking for a moment, Jake shook his head, even though no one was around to see his gesture.

"Not hungry," Jake called back. Jake sat up from his chair and stretched, eying his art one last time. Jake jumped slightly as Dean poked his head into the library.

"I didn't ask if you were hungry, I asked what you wanted to eat," Dean said flatly. It was Jake's turn to roll his eyes, shaking his head slightly to show how annoyed he was, but Dean didn't notice. "Well?" Dean asked, his brows arched in question.

"Fine. I'll have eggs or something," Jake finally replied with a sigh, "Oh, and some coffee."

"Got it," Dean nodded, heading back to the kitchen. Jake scratched the back of his head in annoyance, letting out a deep breath. Before the teen could sit back down to finish his artwork, a flutter of wings sounded throughout the room, leaving behind a trench-coated angel. Jake's sour expression turned warm as he nodded to Castiel in greeting.

"Hello, Jake," Cass greeted.

"Hey, Cassy," Jake replied, giving a weak smile.

"Yo, Cass!" Dean stepped into the library, a plate full of eggs in one hand and a mug of coffee in another. He set the food down on the table then looked at Jake with a stern expression, pointing to the plate. Jake groaned dramatically before sitting back down in front of the food and picking up a fork. Castiel tilted his head to the side, looking at Jake with puzzlement.

"Are you two in some kind of domestic disagreement?" Castiel asked, watching Jake halfheartedly playing with his scrambled eggs. Dean sighed, pulling the angel to the side, out of Jake's earshot. When Dean was sure that Jake wouldn't be able to hear him, he locked his gaze on Cass's.

"Something's up with the kid, he just refuses to eat anything I put in front of him," Dean explained. Cass pondered the hunter's words for a moment, sneaking glances at Jake, who still hadn't taken a bite of his food. Castiel then looked back at the hunter, examining him closely, causing Dean to shift around uncomfortably. "Dude, what?!" Dean snapped, causing the angel to come out of his weird trance. Castiel nodded knowingly, making Dean even more confused.

"Jake is sad," Cass answered flatly.

"Sad? Wait, Cass, how do you know?" Dean asked, cocking his head to the side. Castiel returned his gaze back to Jake, who left his food completely and resumed drawing.

"Dean, being Jake's 'Guardian Angel' or whatever you call it, I can sense his emotions. For example, I know that he is sad," Castiel replied. Dean took a moment to think about Castiel's response before chuckling to himself slightly.

"So uh, would you be able to tell when he's horny?" Dean questioned, smirking to himself, obviously amused with the scenario he had playing in his head. Cass sighed and shook his head slightly.

"Anyway," Cass started, ignoring Dean's immature question, "I can sense that he is upset, but for what reason I am unaware." Dean nodded, his entertained look turning back to that of a concerned parent.

"Well how are we supposed to figure out what's makin' him all depressed," Dean threw himself into deep thought. The angel tilted his head, giving dean a bewildered look.

"Why don't we just ask him?" Cass suggested, almost sarcastically; if angels could even be sarcastic. Dean rolled his eyes again, shaking his head.

"Cass, buddy, we can't just ask a teenager why their upset. He might throw something at us," Dean retorted. Ignoring the older hunter's argument, Cass walked past Dean and strode over to Jake's side. The angel watched quietly as Jake finished shading in the trees behind the galloping deer.

"It's wonderful," Castiel complimented after Jake had finished, the teen putting down his pencil.

"Thanks," muttered Jake, leaning back in his chair with a sigh. The angel traced his finger over the deer, then gave Jake a knowing look.

"You are the deer depicted in this picture, are you not?" Castiel asked soothingly.

"How the Hell did you come to that conclusion after looking at it for no more then five seconds," Jake asked, scoffing.

"Because whenever you focus on your drawing of the deer, your emotional senses increase, leaning more towards the realm of sorrow." Cass replied, his eyes gazing over the drawing.

"Dude, that sounded way more poetic then it should have," Jake said, giving a small smile. The angel dismissed Jake's sly comment and moved to sit in the chair next to Jake, locking their icy blue eyes together. Cass could see Dean from the corner of his eye, the hunter was leaning against the door frame, trying to listen in on the conversation. The angel simply ignored him and kept his focus on Jake.

"You are upset Jake, why is that?" Castiel asked, the angel's eyes searching the boy's face. Jake shrugged, attempting to look away from Castiel's gaze.

"Jake." The way the angel said Jake's name was soothing and gentle, causing Jake to fully return Castiel's stare. Jake was about to open his mouth to speak when Sam came rushing into the library, folders of papers tucked under his arm.

"Guys, I think I found a case."