Thanks to everyone whose read and reviewed and favourited and followed! My life is in a bit of an upheaval at the moment and every single alert I get makes dealing with this a lot easier.

Just so you know, I have never been to Chicago. All geographical information I have gained from Google.

Read on!

...

"It's just here."

Dean glanced up at the house Cas was indicating and pulled into a smooth parallel with the curb, killing the engine and glancing over with a smile.

"So? What do you think?"

"What do I think about what?"

Dean threw his hands up.

"About the car dude?"

"Oh!" He scanned his eyes over the console, the radio that still only featured a tape deck, the black leather seats that were comfy but probably scorching in the sun, and back up to Dean who was sitting in the driver's seat, waiting in anticipation.

Cas smiled.

"She's beautiful Dean. You clearly love this car a great deal. She is well cared for."

Dean blushed and unbuckled his seat belt.

"Thanks Cas."

The drive down had been invigorating, surging down Lake Shore in the black muscle car, Dean guiding her smoothly in and out of traffic as though he were controlling her telepathically. The engine purred and even Cas, who knew nothing about cars, could tell that this one was special.

Along the way, Cas filled Dean in on a few details. The gathering was to celebrate his littlest sister's birthday. Her name was Charlie and she was turning twenty-five and of all the Novak children (of which there were six along with an abundance of cousins), she was adopted.

"My parents couldn't really help themselves." Cas explained as Dean turned off into Hyde Park, navigating the smaller roads with just as much ease and style as he did the highway, "After they had Michael, Lucifer—"

"You have a brother named Lucifer?"

Cas shrugged.

"They wanted to continue the angel theme. Anyway, then they had Gabriel and Anna - Anael - and me and then once we had all grown up and flown the coop, my mom found Charlie. She was sitting alone and crying in a hospital waiting room. My mom was a nurse and she just sat with her. A car accident had taken her parents and she had no other family. She was only twelve, so mom just kind of adopted her on the spot." He smiled at the memory of his mother, "She always did love bringing home strays.

"Anyway. Charlie and Anna and Gabriel will be there tonight as well as Anna's husband Inias."

A frown crossed Dean's features.

"What about the other two? Michael and Lucifer?"

Cas was silent. It was not a topic he enjoyed thinking about, let alone rehashing to famous movie stars he had just met.

"It's a long story." He said with a note of finality.

Dean nodded and swiftly changed the subject to the Chicago Cubs. Cas smiled and nodded along, enjoying listening to Dean talk and not caring that he had absolutely no interest in sports.

They approached the door and Cas rang the bell, his heart jumping and his palms sweating the moment it sounded.

"Umm, just, in advance, I want to apologize. They're wonderful but they can be…I mean…"

"Hey." Dean stopped his rambling with a steady hand on his shoulder. "It's alright. I got family too. Sort of. At any rate, I know what you mean."

Cas smiled and would have been in great danger of getting lost in Dean's eyes again if the door hadn't opened and a red haired blur that was Charlie hadn't mobbed him.

"CASSIE!"

Cas grunted and stumbled under the unexpected weight but hugged her back tightly.

"Happy Birthday Charlene."

They broke apart and she punched him on the arm.

"It's Charlie Cas, or Charles. None of this Charlene bullshit. And thanks." She stared up at him with an adoring grin.

Cas smiled back and glanced over at Dean.

"Charlie, I want you to meet a friend of mine. This is—"

But Charlie was already way ahead of him.

"Holy shit you're Dean Winchester."

Dean chuckled, "Uhh, yeah. Happy Birthday."

She stared between the two of them and then punched Cas again on the arm.

"Have you been holding out on me Cassie?"

"First of all ow." Cas protested, rubbing his arm, "Second of all no. We just met the other day."

She glanced back over at Dean, staring like she couldn't quite believe he was there.

"I have a poster of you hanging in my room right now."

Dean's eyebrows raised.

"Oh? What film?"

"Time and Away."

Dean nodded appreciatively, "Good choice."

Charlie shook her head.

"This is so weird. But good! Good weird."

A voice shouted from inside the house.

"Hey Chuck! You ever gonna let him in?"

"Them!" She shouted back, moving out of the way so Cas and Dean could step inside. "Cas brought a date!"

Cas opened his mouth to protest the word 'date' but Gabriel had already sprinted into the room.

"Cassie brought a date?! Wha—" He skidded to a halt, staring open mouthed at Dean, "Holy crap on a cracker it's true."

"What?! You knew about this and you didn't tell me?!" Charlie yelled back.

"Lord, will you guys quit with all the fighting, what is going on in here." Another red headed woman strode in, wiping her hands on the apron she had tied around her waist. She too stopped short and stared at Dean.

Cas rolled his eyes.

"Guys, this is Dean. He is not my date, he's just…" he trailed off and glanced over, "He's my friend. Dean, this is Gabriel and Anna."

Dean stepped forward with an outstretched hand and a smile.

"Hey, how's it going?"

Gabe and Anna were speechless as they each in turn took Dean's hand. Anna was the first to recover.

"Well, it's very nice to meet you Dean. Come in, can I get you a drink?"

"Do you have beer?" He asked as they moved into the kitchen.

Gabriel watched them go and then turned a beaming smile onto Cas, swatting him playfully on the shoulder.

"Cas! You got game! Who knew? Oh! I have got to text Bal." He turned and pulled out his phone, disappearing into the living room.

Charlie stretched to kiss his cheek.

"Best birthday present ever." She proclaimed before scurrying into the kitchen.

Alone in the foyer, Cas rubbed his arm. Inias still had yet to show up. He might end up needing serious medical attention by the end of the night.

Thankfully, Inias was a little more subtle and gracious in his introduction to Dean, masking his surprise with a handshake and a smile. Armed with a beer, Dean settled next to where Cas leant against the kitchen counter, chatting amiably with everyone and indulging everybody's questions with endless patience.

The meal was excellent, Anna's skills in the kitchen matched only by Gabriel's savant-like talents with baking, and when, at the end of the night, he pulled out a cake with a picture of Charlie dressed in armour, wielding a sword and astride a horse, everyone applauded though only Dean was surprised.

"Gabriel owns a bakery just down the street from the shop." Cas explained quietly as Charlie closed her eyes and wished furiously. Dean nodded and turned to face him before Cas had a chance to pull back. Their noses nearly touched and up close, Cas found himself mesmerized by the smattering of freckles that covered his face and the length of his eyelashes, how they brushed his cheeks when he blinked.

For a split second, the whole world fell away and it was just two of them, sharing space and breath, caught in an eternal moment. That was broken by Charlie's loud voice.

"Alright! Alright!" Charlie spoke up over the din, waiting for the chatter to die down before continuing. "Now that we have supped and imbibed, I think everyone here would like to know how these two met." She gestured at Dean and Cas with her half full wine glass and cheers went up from around the table.

"I already heard from Cas," Gabriel, said, passing out pieces of the cake. He glanced up from his work and stared at Dean, "I want to hear Dean's side of the story."

Everybody cheered again and Cas ducked his head.

"You don't have to if you don't want to." Cas whispered under the din, it was actually astounding how much noise could be made by such a small group of people.

Dean chuckled and patted Cas' thigh under the table, "It's alright, I don't mind."

Cas didn't quite catch the beginning of the story.

Charlie opened her presents slowly and deliberately, giving each her undivided attention and plying each gift-giver with thanks and a hug. She was especially pleased with Dean's gift of an as of yet unreleased Utopia hoodie and poster that she shrieked over before attack-hugging him. The gift was Castiel's idea, Dean had wanted to buy jewelry or a purse but Cas had managed to convince him that Charlie would appreciate this much more.

Once all the presents had been opened and the gift givers suitably thanked, Gabriel piped up with, "Alright, who gets the last slice of cake?"

"Don't you think it should go to Charlie since it's her birthday?" Inias piped up to which Charlie added a boisterous "Yeah!"

"You had thirds." Gabriel pointed out, "I think you've had your fill."

"Well what about you Gabriel?" Anna piped up, ."You baked it, you deserve dibs."

"No he doesn't!" Charlie argued, "If he baked it, that means he ate half the frosting and licked the bowl clean."

"Alright, alright." Gabriel contended, "Well how about you, sis?" He asked Anna who shook her head.

"Oh no. I've had enough. If I eat anything else I'm going to explode out of this dress."

"I think it should go to Cassie."

All heads turned to Charlie.

"What? Why him?" Inias asked, only slightly annoyed he hadn't been included.

"Because his life is so sad." She explained.

"Gee, thanks Charlene." Cas shot back to which Charlie stuck out her tongue.

"Not in a bad way." She explained as though it would help.

"In what way is 'sad' good?" He asked.

"I just meant that it's not your fault and you don't deserve it. You don't deserve a bookshop that's slowly failing or an ex-wife who won't let you see your daughter or that pervert for a roommate."

"Yes thank you Charlie. Thank you for summing up the sadness that is my life. Fine I will take the cake if only to shut you up." He was reaching for the plate when Dean piped up.

"Hey, what about me?"

The whole table froze as though they'd forgotten he was there.

"What do you mean 'what about you'?" Gabriel asked with incredulity.

Dean shrugged.

"Don't I get a shot at the cake?"

Gabriel raised an eyebrow and glanced around the group before sitting back and gesturing for him to continue.

"Vey well, state your case."

Dean shifted and shrugged.

"Both my parents are dead."

Everyone at the table exchanged glances and Inias piped up with, "Yeah, join the club. What else you got?"

Dean nodded as though preparing himself.

"The only real friends I have are a skinny guy named Garth and a burly Cajun named Benny who coordinate my security. I've got a brother I don't talk to and a sister in law I've met once. People assume because of my looks that I have no depth and they're probably right which means that one day, the only talent I have will be gone and I'll just be another forgotten celebrity on some pathetic reality show trying to pay the bills and recapture a time when I was famous."

The table fell silent following his speech, each and every one of them locking eyes.

"Nope! Not buying it!" Charlie proclaimed as she handed the slice of cake over to Cas who ate it with a smug smile plastered to his face.

Dean conceded gallantly.

...

The party wound down eventually, conversations falling off as the bottles of wine emptied and yawns sprang up from around the table. Then the business of bidding everyone goodnight began, Charlie coming round for a second long hug from Dean and passing it off as 'the birthday girl's prerogative'. Anna took advantage of the fact that Dean was busy being seen off by Inias and Gabriel to pull Castiel aside.

"What?" He asked as she tugged him by the elbow into the hall that lead to the kitchen.

She stopped and didn't speak at first, just stood surveying him.

"Are you sure you know what you're doing Castiel?" She asked with a typical concerned older sister tone.

Cas frowned.

"What are you talking about Anna?"

She sighed and looked down the hall to where Dean was chuckling.

"Dean seems lovely. And it's nice to see you finally branching out and meeting new people but I...I just don't want you to get your hopes up too much. I know how much you like him and I know enough not to believe everything you read in those gossip magazines, but Dean Winchester's exploits with women are notorious and I just don't want to see you get hurt."

Cas sighed and looked over at Dean. He was standing near the west facing window and the setting sun was illuminating his face, lighting up his dark blonde hair and casting his head in a halo, his eyes sparkling in the light. He smiled wistfully before turning back to Anna.

"I know Anna. I have no illusions about Dean. I don't expect anything to come of this. I just…" He trailed off and looked back as Dean smiled at something Gabriel had said, "I'm just enjoying it while it lasts."

Anna smiled at him and pulled him in for a bone crunching hug.

"I love you Cassie." She murmured into his hair, "I know life has been hard lately but I'm so proud of you." She pulled back, her hazel eyes distinctly moist and she laughed in the face of her emotional upheaval.

Cas smiled.

"I love you too."

"So…" Dean began once they were back in the Impala and the engine had roared to life. "You have an ex wife and a kid."

Cas chucked nervously.

"Yeah. I uh, I probably should have briefed you on a few things before subjecting you to my family. They can be a little intense sometimes."

Dean shrugged, and he grinned easily, tension flowing out of his body now that he was away from the hungry mob. Or perhaps it was an effect of the car. The way Dean spoke about her and steered her made him think she was more than just a machine to him.

"Family ought to be like that." He murmured enigmatically. "So, you gonna tell me about them?"

He glanced over expectantly and Castiel nodded obligingly.

"I met Amelia when I was very young. We went to the same church and were involved in the same youth outreach program. When we were old enough to be invited to the church socials, it was pretty much expected of me to ask her. And when I graduated from University, I went shopping for a ring and that was that. There was no question, there was no alternative. I kept waiting for things to get…better. And they did, when Claire was born and I held her for the first time, it all seemed…worth it.

"A few years after my Dad handed the reigns of the shop over to me, he had a stroke. It was very sudden and it made me reexamine a lot of things. I started to think about my life and what I would have to show for it when the end came. Sure there was the shop and Claire…but I felt like something was missing. Like something didn't fit. It took me an embarrassingly long time to figure it out and when I finally sat Amelia down and explained that I was…gay, she couldn't accept it. She tried to convince me that I was 'sick' that just needed 'help' and when I refused, she threatened to take Claire away from me. And she did. I haven't seen my daughter in nine months. To make things worse, the whole situation has divided my family down the middle. You met the ones who sided with me tonight."

He trailed off and tried to ignore the burning behind his eyes. He would not cry in the presence of Dean Winchester. The man probably thought he was a wuss anyway.

"That sucks." Dean murmured and Cas glanced over and smiled softly.

"I'm not completely innocent in all of it, but thanks."

They drove in silence for a while, the windows rolled down and the cool evening air invigorating Cas as they sped along Lake Shore Drive. It was a comfortable silence which surprised Castiel since he wasn't generally comfortable being in the company of anyone. But with Dean, it just seemed right somehow. He felt calm in his presence, for once not feeling pressure to be anyone or anything. He was free to just be Cas.

They hadn't been driving long when they turned off the main road and Dean navigated the exits until they were parked in the north end of Burnham Park and Dean was exiting the car.

He ducked down and peered in at Cas who hadn't moved.

"You coming?"

"Coming where?" Cas muttered to himself as Dean straightened and slammed the door.

Cas unbuckled his seat belt and stood, shutting the door and joining Dean as he locked the car and began moving toward the lake.

"Where are we going?" He asked as they walked along the grass, the lake stretching out in front of them as the sun set behind.

"You've never taken an after dinner stroll?" Dean asked with a smile.

Cas shrugged.

"Sure I have. It's just you don't seem like the stroll type."

Dean laughed, and Cas was pleased to see that he did indeed laugh with his whole body, head thrown back in mirth. The sight and sound warmed Cas' heart.

They walked to the water's edge, looking north to the city skyline that was bathed in an orange glow and then turned south for a bit until Dean slowed to a stop and plunked himself down on the steps that followed the manmade shore line. Cas took a seat beside him.

"My mom died when I was four."

His voice was soft, quiet. Lacking in the self-assuredness that normally coloured it.

Cas didn't comment, just glanced over, giving him his full attention.

"A fuse shorted and…" He trailed of and snapped his fingers, "The fire started in my brother's nursery. Mom woke up, Dad was asleep downstairs. It was the shouting that woke me. I ran into the hallway and Dad came out of the smoke with Sam - he was only six-months - and he pushed him into my arms and told me to run. So I ran. And I stood out on the lawn, waiting…but she never made it out."

He was staring off into the distance, out across the vast expanse of lake as the light dimmed.

"After that Dad sort of…faded away. Like he was there, but he wasn't. Didn't help that he was seeing the world through a steady stream of bottles. I think he felt like he wasn't cut out to be a parent without mom so he just fell back on what he knew, which was being a soldier. He was a marine, served in Vietnam, and that's how we were raised, like we were recruits, not his children. So it fell to me to look after Sam, feed him, clothe him. Dad would go off looking for work and leave us for days on end. I tried my best but it must not have been enough cause the minute he was old enough, Sammy was off like a shot. Full ride to Stanford and he didn't speak to me for three years. Dad got even more distant after that, like it had been my fault that Sam left. And then I was on my own and broke.

"I was sitting in a diner just outside LA when I was approached by a scout for a modelling agency. It was pretty stupid, but it paid the bills and I kept getting calls so I kept doing it. Got an apartment, settled in. When I landed my first major spread I sent it to Dad. He called me up to congratulate me on becoming a painted whore." He smiled bitterly and Castiel frowned, "A few months later he was gone. Liver failure. I saw Sammy at the funeral for the first time since he'd left but he had someone already and he was happy, away from me. So he went back to Law school and I went back to the City of Angels and transitioned smoothly from modelling to acting. I guess I got enough practice pretending to be someone else growing up, trying to pretend I was my dad's good little soldier boy."

He fell silent, staring out at the water for another long moment before the spell was broken and he laughed.

"I've never told anyone the whole story before." He turned to look at Cas, "You're a good listener you know that?"

Cas smiled.

"Thank you for telling me Dean."

"No problem Cas." He shifted forward and let his clasped hands hang between his knees. "It's refreshing, talking to you."

"Why?" He asked with a frown.

"'Cause you're real. You get famous and people start wanting things from you, so they lie. It gets to the point where you can't even tell what's true anymore. Tonight was great 'cause it was real. Those people, your family, they were real. The love was real."

"That's very depressing Dean."

He chuckled, eyes crinkling at the corner. Cas liked it, would like to see more of it.

"Sorry to be such a downer."

"No, it's alright, fits right into my life."

Dean looked over.

"Yeah, aren't we a couple of sad sacks. A movie star and a guy with a loving family."

Cas frowned thoughtfully.

"Well, when you put it that way…"

They sat until the sun went down. Cas found Dean's hand in the dark and squeezed it, just to let him know he was still there.