"Cas," Dean groaned as he pointlessly tried to rub out the fresh worry lines on his forehead. He had thought after an old girlfriend making him try on her pink silk satin panties, he'd never feel more awkward. Well, his current best friend was definitley challenging that. "Is that why you took me to this nice restaurant? To butter me up?"

Cas looked at him in desperation his hands clasped together, "Please, Dean! It's just one night, barely two hours. Then, I'll never ask anything of you ever again."

Dean opened his mouth to speak, but the waitress came with their orders, "Steak dinner for the big guy and double cheese burger for the cutie in the trench coat. Anything else?"

"No, that will be all. Thank you," Castiel dismissed her politely without looking away from Dean. Dean narrowed his eyes at the overly flirtatious waitress as she winked at Castiel before walking away. Castiel didn't pay her any attention, though.

"Hey, maybe you should ask her," Dean threw his thumb over his shoulder in the direction the waitress went, before starting in on his steak, "She seems more than willing."

Castiel sighed, "My family knows of my," his eyes shifted away awkwardly before continuing, "preferences. They have tried repeatedly to set me up with lawyers and doctors from well brought up families. If I have to sit through another blind date with a character like Balthazar, who arrogantly can't stop talking about his many achievements in life, I will go insane. Please, Dean, help me. If they think I'm taken, they'll stop."

Dean eyed his plate chewing thoughtfully, avoiding Castiel's pleading gaze. He was going to break and he knew it. He couldn't deny Cas anything when he was begging like that, but he really didn't want to do this. "Cas, even if I do this, do you really think your family will be happy with a guy like me dating their son? Hell, they'll probably try even harder to find you a more suitable partner."

Cas looked at him sadly, "Dean, I don't understand why you think so low of yourself. Working towards a degree in architecture and design is highly admirable. Besides, I'm sure my family will respect whoever I decide to bring home, regardless of occupation."

Dean was doubtful of that, but his last will of self preservation was long gone as Cas's blue eyes pleaded him. He groaned in defeat, "Fine, but just this once. I'm not doing this again, Cas. I don't do parents even in real relationships."

A wide grin broke across Cas's face and reached across the table and grabbed Dean's hand and squeezed it tightly, "Thank you so much, Dean. It means a lot to me."

"Sure, Cas," Dean pulled his hand away already feeliing like he was going to regret all of this. He cleared his throat and dug back into his meal, "What are friends for." Cas smiled at him and turned back to his food as well.

Yeah, what are friends for if not to pretend to be your best friend's boyfriend in front of his whole family? Dean was not looking forward to Friday night having dinner with Cas's family role playing as a couple. Dean didn't really want to see Cas's family's disappointment when they met him. He was well aware of what kind of people the Novaks surrounded themselves with and Dean's payroll was nowhere near what those people made. He didn't know much about the Novaks or the many siblings. He just didn't want the Novaks to give Cas any shit about dating him, even if it wasn't real. Cas was his best friend and he cared about the guy. He could do this for him. He just hoped he wouldn't screw it up.

"You look," Cas's wide eyes raked up and down Dean's body, "nice." Dean was dressed in a maroon button up shirt and his best fitting jeans. It was the most formal clothing he could find in his closet and he had been pretty satisfied with his findings when he left his apartment. But looking at Cas in his black slacks and blue tie, he was starting to rethink. But Castiel didn't comment any further, walking back into the apartment looking for his coat, leaving Dean at the door.

"You didn't say it was formal or anything, so," Dean followed Castiel to find him in the small den, shrugging into his tan trench coat, "Are you sure this is okay?"

"Yeah, it's fine, Dean. I just don't have any more casual clothes clean at the moment."

Dean laughed, "Really, Cas? Too lazy to take your clothes to the laundromat?"

"Not lazy, just procrastinate the annoying task," Castiel corrected as they walked in the parking lot towards Dean's Impala.

Dean blared Metallica music loudly on the drive to the Novak household, and even though Castiel wasn't too fond of it he didn't say anything because he knew it was calming for Dean. Castiel understood Dean's nerves. He was wondering himself how they were going to pull this off.

"Holy shit, Cas," Dean let out a whistle as he parked in front of the enormous house. It was twice the size of his parents' and their's was a two story. "I knew you were loaded but damn."

Cas sighed beside him, "Yes, well as beautiful as the house may be, I prefer the Winchesters' home more comforting."

Dean looked at him sadly, but before he could comment, Cas was out of the car. From what Castiel had told him, Dean knew that Cas felt that he didn't really fit in with his family. He had said that he just felt too different from them. Unlike his older siblings who had perused medical careers and other wealthy positions, Castiel was an art major. Cas had told him that even though his mother assured him it was his choice, they looked at him strangely after that. Dean didn't really see Cas's family as shallow, but was sure they liked to have the best of everything.

Castiel walked to the door slowly as if trying to extend the time before he had to see his family with Dean by his side. Castiel paused in front of the door, but made no movement for the doorbell.

"Hey," Dean whispered and slipped his hand into Cas's, rubbing his thumb in soothing circles, "It's gonna be fine, Cas."

Cas nodded his head and glanced at their intertwined fingers and back at Dean with a slight question in his eyes. Dean just winked at him, "Boyfriends, remember?" and rang the doorbell.

"Right," Cas's shoulders slumped, instantly relaxed with Dean's touch. The door swung open and Dean felt Cas squeeze his hand subconsciously as a short man beamed at both of them.

"Well, hey there, Cassie. Who's tall lean and handsome? You the one shacking up with my brother?"

Dean gapped at the guy front of him wiggling his eyebrows suggestively with a smirk that Dean guessed was a constant on the man's face. He didn't exactly know how to respond to that. He glanced at Castiel beside him, who was glaring at the guy.

"Gabriel," Cas drew out frustrated, "This is my boyfriend, Dean. Dean, my brother Gabriel. I would appreciate you to restrain from using terms such as shacking up. It's inappropriate."

Dean plastered a charming smile on his face and held out his free hand, "Nice to meet you."

Gabriel didn't lose his smirk, but shook Dean's hand. "Strong grip. Please come inside," Gabriel released Dean and stepped aside, dramatically bowing for them to enter. They crossed the threshold hand in hand and Dean should have known then that everything was about to be the change.

They discarded their coats and followed Gabriel through the white paneled halls. Dean couldn't help but marvel at the Novaks' home. It was beautiful. The floors were marble and abstract works of art covered the walls. The one term that rang in Dean's ears was expensive. With the small decorative figurines that seemed to be everywhere, Dean felt like a kid in a museum, encouraged to look, but never to touch.

Gabriel led them to the living room where the rest of Castiel's family was waiting. Dean took a sharp intake of breath at the number of the people in the room. He knew that Cas had a lot of siblings, but were there really that many? There was six other men in the room and two small women. They were chatting amiably with each other, but the talk quieted to murmurs as the trio strolled in. Dean, for the first time tonight, felt a bundle of nerves rolling in his stomach.

"Everyone, may I introduce Cassie's prince charming here, Dean," Gabriel gestured and everyone's eyes shifted to Dean expectantly.

Dean nodded at them, "Hi, I'm Dean. It's nice to meet you all." That sounded really nervous, even to Dean. He could be quite charming when he wanted to be. He didn't know what it was about the Novaks that made him feel like he was in highschool picking up Cassie Robinson for prom again.

There were small hellos and polite smiles thrown at Dean, before they quickly went back to their conversations. Dean let out a breath he didn't know he had been holding and Castiel's hand slipped back into his comfortingly like Dean had done earlier. It was funny how it came so easily and felt natural to them both. The older of the two women made her way to where Dean and Cas were standing with a wide smile. She was blonde and her black heels clicked against the floor. Dean assumed she was Mrs. Novak.

"Castiel, it's so good to see you," she greeted Castiel with a hug that she then gave to Dean, "And Dean, it's nice to finally meet you. I'm Rebecca Novak, Castiel's mother. I've heard a lot about you from Castiel, but I never knew you two were so close."

Dean chuckled, "I guess you could say we danced around it for a long time." He figured that was a vague enough lie. He glanced at Castiel before turning back to Rebecca, "Hope you haven't heard anything bad."

Rebecca laughed, her eyes flickering between the two, "No, all good things."

A man with a scruffy beard cleared his throat and everyone gave him their attention, "Naomi tells me dinner is ready."

Dean figured giving the authoritative voice it was Castiel's father. Everyone followed after him to the dining room. Dean sat at the edge of the table with Cas on his left and a red haired girl across from him. They ate dinner, the family making small talk with each other, who was doing what, who married who, and barely anyone even acknowledged Dean until halfway through dinner.

"So, Deano," Gabriel called from further down the table, loud and disruptive, "What do you do? You a color by numbers like Cassie?"

Dean met his eyes and saw that everyone's were on him, waiting his answer. He felt Castiel stiffen beside him, his eyes cold glaring at his brother.

"No, I'm in architecture and design," Dean answered, uncomfortable under the curious gazes on him.

Gabriel made a noise of approvement and seemed to have initiated the string of questions that soon followed.

The clean cut guy that was on Mr. Novak's right at the head of the table spoke, "Sounds like a successful career. Do you have any idea where you'll work after college?"

"No, not yet. I only have two years under my belt, though. Guess I haven't thought that far yet."

"At least you can do something with a degree in architecture," a man from the other side of the table said in a deep voice and the room grew quiet, "Not like ceramics."

"Raphael," Rebecca scolded from beside him in a warning tone. He rolled his eyes, but didn't say anymore and continued eating. Dean looked at Castiel who avoided his worried gaze and kept his eyes on his plate. Cas must get a lot of those kind of snides by the expressions of everyone in the room. Cas looked like he was used to it in the submission of his shoulders and that was what set Dean off. Cas didn't deserve to be talked down to like that. Dean didn't care if the guy was his brother.

"Actually, Ralph," he spoke as he took a sip of the wine and everyone turned their heads to him in shock, "Cas is a painter. So, taking a class that has to do with sculpting pots out of clay would be pointless. Cuz that's what ceramics is if you didn't know. Cas's major is studio arts and he's even had several pieces displayed in the art gallery."

There was several snickers heard from behind hands and downright laughter from Gabriel. Raphael's face looked like he wished he could smite Dean where he stood. Cas's was just in complete bewilderment and awe. He didn't say anything, though, and Dean wondered if he had crossed a line. But he was reassured as the corners of Cas's mouth turned up into a small smile.

The girl across from Dean who had looked dull and bored all night, face perked up and she leaned towards Castiel, "Really, Castiel? You have pieces in the art gallery? Which one?'

Castiel grinned at her and Dean could tell he was fond of his sister, "The Cider Gallery."

"That's great, Castiel. I'm proud of you."

"Thank you, Anna."

Dean decided Anna was an okay character, not like the others who were more interested in their doctor friends. Her and Castiel continued to talk and Dean just quietly listened until something sparked his interest from the older brothers' conversation.

"I heard Balthazar just bought a new summer home in Italy."

"Italy? God, doesn't the guy have a giant mansion in California? What's he need a house in Italy for?" Gabriel scoffed.

Michael raised his glass, "Well, when you work as hard as he does, you deserve houses in foreign countries. They gave him another raise at the firm."

Rebecca nodded, "Yes, Balthazar is a fine man."

Dean frowned as he felt something churn in his stomach. He felt uneasy about the conversation, but he didn't know why. Before Dean could shift his attention else where, Gabriel caught his eyes and gave him a mischievous smirk.

"Cassie, you went on a date with ol' Baltzy didn't ya?"

Castiel looked taken aback by the question and he glanced at Dean. "Well, uh, yeah, but it was just once."

"So, who's a better kisser? Deano or Baltzy?"

Castiel almost chocked on his food and opened his mouth to say something, but quickly shut it, his lips set in a hard line. Gabriel grinned like it was the reaction he had been going for.

"Oh, come on, Cassie. I mean you guys have kissed before right since you're a couple and all."

"Of course," Castiel said too quickly and Gabriel noticed, but didn't comment. Dean could tell, though. Gabriel was starting to pick up on the not-too-couply vibe from them.

Rebecca tried to steer the conversation to something more appropriate for the dinner table, "Lucifer, how is the hospital treating you? Do you feel overworked?"

"Well,..." and with that the siblings didn't give any more attention to Dean and Castiel's relationship for the remainder of the night.

It was the end of the night and most of the siblings had wandered off to their rooms, but some stayed to say their goodbyes to Dean and Castiel in the foyer; Castiel's parents and Gabriel.

"It was a nice evening. Thank you for coming, Dean," Rebecca hugged him and then her son.

"Sure, thank you for welcoming me into my home."

Mr. Novak, who Dean never caught the first name, said goodnight and walked up the stairs with his wife, leaving only Gabriel. He had been quiet since his uncomfortable question at dinner and had a quizzical expression.

"You know, you two don't seem very intimate to me. You haven't even touched each other all night," Gabriel raised his eyebrows at the distance between Dean and Castiel.

"Um, well," Castiel searched his mind for a response, but Gabriel stepped closer and interrupted his excuse.

"And bringing a fake date seems just like the kind of thing you would do to get mother off your back."

"Listen, Gabriel," Castiel started looking a little pale, "Dean is not a fake date."

"Uh huh," Gabriel said unconvinced, "Then prove it to me right now."

"Prove?"

"Yeah, kiss," Gabriel spoke with a smirk. When Castiel didn't respond he continued, "See, I knew it. Wonder what mother will do now, knowing you tried such a tactic. Probably punish you with an arranged marriage."

Castiel sighed and looked defeated, "Okay -"

But Dean cut him off, grabbing Castiel's surprised face and pressing their lips together. He only meant for it to be a quick kiss, but he felt Cas's lips start to move with his own and he couldn't help but forget the other person in the room. Their lips separated and they met each other's eyes. Cas's cheeks were tinted pink and he looked breathless. His eyes were wide and had a curious look about them, but Dean wasn't sure. They broke apart and Dean turned to Gabriel with a smirk. The guy looked surprised but the smug expression hadn't left his face.

"Cas just isn't overly affectionate in public, Gabriel. You don't have to accuse him," Dean said as he pulled on his jacket.

"Guess not," Gabriel spoke amused, "Well, goodnight. It was a pleasure, Dean."

They walked to the Impala in silence, neither of them not looking the other in the eye. The drive was quiet, but it wasn't comfortable like earlier. It was tense and awkward, so Dean turned up the radio not knowing what to say to Castiel. A few minutes later he pulled up in front of Castiel's apartment building, but Cas didn't move to get out.

Dean sighed and turned down the radio, waiting for Cas to say that Dean had taken it too far and he didn't feel comfortable around him anymore. "Cas, I'm sor-"

Cas cut him off, "Thank you, Dean."

"Uh," Dean's voice shook, wondering what exactly Cas was thanking him for, "Yeah, sure thing, Cas."

"For sticking up for me," Castiel clarified, finally met his eyes and Dean felt something twisting in his stomach as he stared into Castiel's blue eyes, but he couldn't place the emotion, "Raphael is always very condescending and disapproving of my choice in major."

"Yeah, dude's a douch," Dean didn't leave any of his dislike for the guy out of his voice.

Castiel chuckled, "Yes, it's hard to put up with him."

They didn't break eye contact and it should have felt awkward, but it wasn't. The moment was intense like they were speaking to each other without saying anything, but Dean couldn't hear what Cas was trying to tell him. He felt something warm and secure sitting there with Cas in the cab. The kiss flashed through his mind and he looked at Cas's lips. He'd never noticed how pink they were and he remembered how they had been rough along with Cas's stubble. But Dean couldn't bring himself to say he hadn't enjoyed it. Suddenly, he was brought back to reality and realized how close him and Castiel had gotten and he could feel Cas's hot breath on his face.

Cas glanced at Dean's lips and back to his apple green eyes. Dean could hear his heart pounding in his ears. He leaned closer, without thinking and something flashed across Castiel's eyes, but Dean didn't catch it before Cas turned away grabbing the door handle. "Really, Dean, thank you for tonight. I'll be sure to make it up to you," he said quickly and left the car, strutting towards his apartment.

Dean looked after him wondering what the hell had just happened. After he lost view of Castiel, he pulled out headed for his own place. The whole drive, Dean felt uneasy like something important had happened that night and changed between him and Castiel. He shook it and told himself he had just been helping his best friend out. Nothing had changed. And if it had, he didn't know what he was going to do about it.