"He looked at me with serious eyes, but not the kind that made me wonder what I'd done wrong. The kind that made me wonder what I'd done right."
-Denise Jaden

Let it never be said that Dean Winchester did not go after the things he wanted. He called Kali when he got home from The Roadhouse, pacing the length of the deserted living room, TV on with the volume turned down. He'd never done anything like this in his entire life. He never had to. Guys, girls, they all just came to him, all with the understanding that the soft tenderness in the backseat of a run-down car only lasted a night. Dean didn't want to have Castiel for only a night. He legitimately wanted to take the other man out on a date, but he really didn't know how. Which is why he needed to find out if Castiel would be free for lunch tomorrow.

"Drs Novak and Novak, this is Kali, how may I help you?" The bored, honeyed voice came over the phone when Kali picked up. Dean could almost imagine her inspecting her nails as she spoke to him.

"Hi Kali, this is Dean…Winchester." He flopped onto a comfortable black leather couch, fingers tapping on the armrest.

"Ah, Mr. Winchester. What can I do for you? Would you like to be passed over to Dr. Castiel?" There was a smug quality to Kali's voice that was rather ingratiating, but gritting his teeth, Dean pressed on.

"No, no. I wanted to ask, does Castiel have any scheduled appointments around 1PM tomorrow?"

There was a pause, and Dean heard the clicking of keys on a keyboard on the other side. "Castiel has no appointments from 1PM to 3PM. Would you like to schedule another session?" Kali asked.

"No, no it's fine, I uh, I just realized I have something I need to do." Dean cast wildly, looking around. "Thanks Kali." Hurriedly, he ended the call and tossed the phone onto the couch beside him, slumping in his seat.

He was actually going to do this. He was going to try and ask Castiel out on a date. Not that he'd done anything like this before. Never. Not once. If this failed, he'd freak out and change his therapist and never see Castiel again. (Oh god, never see Cas again? Maybe he'd have to leave New York! Fuck! Wait, stop, stop, he hadn't done shit yet, let's not get carried away…)

"Dean?" Dean paused in his relentless pacing, and turned to Sam, who had apparently just walked in, coat in one hand and briefcase in the other.

"Hey Sam." Dean stopped short and plastered on a smile. "What're you doing home so early?"

"You're going to wear a groove in my carpet." Sam joked. "What's up with you?"

"Nothing." Dean answered automatically, picking at his shirt.

Sam's eyes narrowed. "Dean. What. Is. Going. On."

"I'maskingCasout!"

"What?"

"I'm asking Castiel out. On a date." Dean thrust his chin out defiantly.

"Are you insane?" Sam yelped. "You're asking Dr. Castiel out on a date?"

"Why not?" Dean stared at his feet defensively.

"He's your therapist Dean!" Sam folded his arms. "That's a disaster waiting to happen."

"No it's not." Dean sighed. "Look, Sam, just let me ask him alright? If he says no, I'll leave it at that."

Sam frowned. "I don't think there's an outright law against it, but it is kind of against their ethics code."

"Sammy, if he says no, that's it okay? It'll be fine."

"Just be careful, Dean." Sam's eyes softened. "I don't want you to get hurt again."

"Sam, I'm not fragile." Dean took a step closer to his brother. "I won't break."

"I don't want to lose you." Sam's voice was level, but the naked fear in his brown eyes broke Dean's heart.

"You won't lose me, Sammy." Dean got a sharp blast of nostalgia.

The stink of fire is heavy in the smoke filled air. Dean's eyes sting from the haze, and baby Sam is crying. His wails resonate in Dean's ears, and he coughs, covering Sammy's tiny body with his own, shielding him as much as possible. "It's gonna be okay Sammy." Dean whispers as he huddles with his brother on the wet grass.

"It's gonna be okay, Sammy." Dean hugged his brother. "You won't lose me. I'm going to be here, always."

"I'm sorry, Dean." Sam's enormous body seems tiny in Dean's embrace, like the night of the fire. "I should've been there, I should've…"

"It's okay, Sammy." Dean soothed. "It's not your fault."

"I got into a fight, with Anna and Gabriel when I found out about you." Sam sighed, once they'd settled down on the couch. "It's the only time I've yelled at them."

"I get they're your parents Sam. I respect that." Dean looked over at Sam. "Kid, I've learnt some things in my life, and one of them is to not play the blame game. Don't blame yourself or anyone for the things that happen. They just happen, regardless of what you do or don't do. There's no point in wondering what might've happened or what should've happened."

Sam looked up at him. "Wise words."

Dean shrugged. "It's part of being a big brother."

Sam smiled. "Either way, I'm glad you're around now."

"Sam, even if I'm not around, I'll never stop being your big brother." Dean told him, gruffly.

"I'm not going to make you stay here, Dean." Sam patted Dean's arm. "I know you've got your own life back at Lawrence."

Dean ruffled Sam's hair. "They grow up so fast." He smirked at Sam's indignant squeal, and got up. "C'mon Sasquatch. I found this great diner across the street that sells awesome pie."

"Hey Ellen!" Dean called cheerily as the brothers walked through the doors of the Roadhouse. Sam patiently waited to be introduced, and Dean gestured to his brother.

"This is my brother, Sam Milton, Sam this is Ellen Harvelle, owner of the Roadhouse. She bakes one of the best pies in town." Dean chuckled at the look of fond exasperation she gave him. He'd been coming in here almost every day in the entire month he'd been here.

"Hi there, Sam." Elllen gave Sam a motherly glance. "Go and take a seat, the two of you, and I'll get some pie while you look at the menus."

"What pie is it today?" Dean asked, eagerly.

"Cinnamon Apple." Jo replied, tying on her apron as she walked through the back door. "Good morning Dean Winchester."

"Good morning Joanna Beth. I would tip my hat but…" Dean gestured to his hat-less cranium with a sardonic grin.

"You must be Sam!" Jo exclaimed, suddenly noticing the large human seated opposite Dean. "I'm Jo. Ellen's my mom."

Sam, though obviously startled, smiled and shook her outstretched hand. "Hi Jo."

"Dean talks about you a lot. He talks about Castiel a lot too." Jo confided in a low voice, wincing when Dean kicked her foot. "Ow! Fine, I'm going I'm going."

"Made some friends huh?" Sam's eyes were light with humour, and Dean had to laugh.

"Ellen and Jo are nice. We got to talking, especially since I come in pretty much every day."

"Is NY that boring?" Sam chuckled.

"Nah, it's just those artsy tourist places aren't my cup of tea. I'd rather be eating pie in here. Or walking in Central Park. Reminds me of those woods behind Bobby's scrapyard." Dean told Sam.

"I used to feed the ducks there when I was little. Mom used to take me for really long walks, especially back when we had Tricky, our dog."

"You had a dog?" Dean asked, pointedly ignoring the fact that Sam called Anna 'Mom'.

"Sure did." Sam nodded. "He was a golden retriever. He died when I was sixteen."

"I'm sorry. We had an old cat at the orphanage. The guy in charge, ol' Danny Shelby, he didn't like cats much, so the other guys and I fed her and kept her in a cardboard box in the shed. When Danny found out, he didn't take it too well." A shadow passed over Dean's face. "We all got a good beating that day."

Sam's eyebrows bunched together. "How old were you?"

"Eleven? Twelve? I don't know. Doesn't matter anyway. I was sent to a different home when I turned thirteen."

Sam's eyes widened. "How many homes have you been in?"

"A bunch. I never kept track." Dean said, saved from having to elaborate by the arrival of the pie.

Tucking in, Dean groaned. "Goddamn this is wonderful."

Sam chewed slowly and swallowed. "This pie is amazing."

"Didn't I tell you?"

"Oh, Dean?"

"Yeah?"

"I have a confession to make."

"What is it?" Dean's fork paused in its migration to his mouth.

"I have no idea what a '67 Impala is." Sam grinned sheepishly.

"But…my car…"

"Yeah I don't know much about classic cars."

Dean gasped. "No brother of mine…" They spent the rest of the day discussing classic cars, and went home to Jess making lasagna.

Dean, mouth watering at the aroma of oregano and basil wafting from the kitchen, pulled Jess into a hug. "I'm so glad my brother's marrying you." He told her, fervently.

Jess snickered. "Go and wash up, you two. Dinner's almost ready."

Sam kissed his fiancée and the two brothers made for their separate bathrooms. After washing up, the gathered at the dining alcove for dinner. Sam made a point of bringing Castiel up as soon as they had all sat down to dinner.

"Dean's going to ask Dr. Castiel out." He informed Jess, as Dean took a sip of his chilled beer.

Dean glared at him over the neck of the bottle, but nearly choked at Jess's reply.

"About time, don't you think?" Jess said, coolly, pouring herself some white wine.

"You knew?" Sam gaped.

"Haven't you heard the way your brother talks about Castiel? You'd think the man was an angel." Jess rolled her eyes.

Dean spluttered. "I'm right here! And I don't always talk about Cas!"

"You even have a nickname for him." Jess pointed out, waving her fork for emphasis.

"A nickname doesn't imply anything!" Dean protested.

"But you asking him out does." Jess paused. "Just be careful. He is your therapist, you know."

Dean huffed, but didn't say anything in reply. From there, they moved on to more innocent topics of conversation but Dean was stuck on Castiel in his mind. Was it really that bad an idea, that both Jess and Sam were telling him to be careful? If Cas didn't want to go out with him, he could just say so, Dean wasn't forcing him. (Dean would have to change therapists out of sheer mortification though.) It wasn't as though he was in love with Cas, he just wanted to get to know the man better and if possible pursue a romantic relationship. Castiel was different, a new species, and he fascinated Dean endlessly. He made Dean laugh, and talking to Cas was a real pleasure. (Plus he was fucking gorgeous.)

Dean had spent his entire life not getting what he wanted, and by then he'd become a firm believer in getting it yourself. Which was why he was going to go down to Drs. Novak and Novak tomorrow and ask Castiel Novak out on a proper date.

"Dean?" Sam stopped Dean on his way back to his room from the dining alcove.

"Yeah?"

"It's not that big a deal, so go for it." Sam grinned. "Don't be nervous, I'm sure it'll go fine."

Dean swore, sometimes Sam could read his mind. "Thanks, Sammy. I'll ask him tomorrow."

Lucky for Dean, Castiel was on his way out of the building when Dean arrived, breath misting in the cold NY air. He beamed at the other man, stuffing his hands in his jacket pockets. "Great, I thought I would get here too late."

"Too late for what?" Castiel cocked his head to the side. "Did we schedule an appointment for today? I apologise if I have forgotten."

"No, no!" Dean shook his head. "I came here to ask if you wanted to grab some lunch."

Castiel sighed, looking relieved, his ordinarily pale cheeks reddening attractively in the cold. "That would be nice, Dean. I normally eat alone, this would be a nice change."

Dean mentally punched the air in victory. "Awesome!" He said, breathily. "Know anywhere?"

"I believe there is a new restaurant open down the street. Would you like to try that?" Castiel suggested.

"Lead the way." Dean winked.

He tried not to hyperventilate like a thirteen year old girl when Castiel gave him a small but warm smile.