Author's notes: Ok So this is a long chapter, I'm having trouble figuring out where to leave off. The feels are strong in this chapter. Dean and Cas finally meet up again, so your waiting has not been for naught! Please let me know what you think. I am pretty happy with this one.

Read and Review it is much appreciated.

February 2013

Balthazar is easy. Balthazar is fun.

Castiel doesn't want textbook, Castiel wants wild and dangerous and Balthazar has that in truckloads. Studies almost forgotten Castiel follows him everywhere, clubs, late night boat rides, shows, concerts, fancy dinners. To be honest Castiel doesn't really know what Balthazar does for a living and frankly he doesn't care. Joshua long since forgotten, Castiel's life expands beyond school and the handful of friends he has. The life is crazy, the partying is crazy, the sex is crazy and the only hang up is that there is none. Castiel just wants to have fun, and Balthazar seems content with that.

Since College Castiel has been fiercely independent, only seeking out company when he truly desires it but able to be social when appropriate. Relationships came and went more often then he cares to remember, being a good boyfriend hasn't been a priority of his for quite some time. Sex used to mean something to him, but now it's just a pleasurable past time. With his bright blue eyes, dark brown hair and eternal 5 o'clock shadow Castiel had always been able to find a willing participant to take the edge off.

'I don't want to be an English Professor.' Castiel whines through pouted lips as he slowly begins hitting his head against the textbook he is supposed to be reading.

'Oh shut it, four eyes you love this boring crap.' The redhead across from him didn't even bother looking up from her laptop as she furiously typed away at it.

Charlie was probably Castiel's best friend. They met sophomore year at a party where they both had a little too much to drink. Still not completely over his breakup from the year before Castiel was confused and had begun to question whether or not he was gay. His solution: sleep with a girl. It wasn't until they had both gotten down to their underwear on some guy's bed at the frat house where the party was, that Castiel burst into a fit of giggles that eventually led to gross sobs. Though drunken, Charlie; bless her little nerdy soul, seemed to sober up enough, to collect him in her arms and talk him through his melt down. By the end Charlie had confessed she was a lesbian and was just confused and worried that her parents would not love her if they knew. Castiel confessed he was gay and had never doubted it until recently when his world had fallen apart. The next morning over a greasy breakfast the two realized they had more in common then they had originally thought.

Friendship was inevitable.

'I just want sleep!' He drawled on.

Charlie scoffs at him. 'Well maybe if you slept at night instead of fornicating all the night through, you wouldn't be so tired! And don't even try to deny it, I can hear you guys going at it. Indecent if you ask me-'

'You live across town, Charlie. I highly doubt either Balthazar or I are that loud when we are intimate.'

'And once again my sarcastic humor evades you, my young Padawan. Also: Wanky.' She winks at him across the table. 'Come on, hurry up! I NEED coffee and you owe me from last week, so I am cashing in my ticket on that.'

Thirty minutes later the two friends were walking arm in arm through the snow on campus to the Hallowed Grounds coffee shop nearby.

March 2013

'What was his name?'

Dean stares across the bar at the bottles of multicolored liquors, avoiding Benny's gaze. How had they even gotten on this subject?

'Who?' Smart one Winchester, play dumb.

'The guy who broke your heart, the one in Kansas.'

He licks his lips. Tapping the bar, he signals Benny for another drink.

'If I remember correctly I believe I told you to drop it.' He eyes the beer in front of him, drawing a swirly design on the glass.

'Can't blame a brotha for tryin.' He chuckles. 'You plan on being here all night? I can get you some grub.' He motions vaguely to the kitchen.

'Naw man.' He rubs the back of his neck tiredly. 'I've got to head out after this one actually. I have to go into the office tomorrow and put the finishing touches on some marketing proposals.' He takes a big drink, enjoying the bitter taste in his mouth.

Benny wanders around the bar refilling drinks and taking orders. Friday nights are busy and some of these guys can be real divas if they don't get their cosmos as quickly as possible. And Benny is just not in the mood to get snapped at tonight, not again. A good amount of time passes before Benny is able to give Dean any attention again, and by then Dean is finished with his beer. He packs up his things, and puts some money down at the bar giving Benny and sarcastic smile and a wink to follow. Benny laughs it off and turns away to put the money in the register.

'Benny.'

Benny turns and sees Dean awkwardly standing by his stool. He looks torn and tired, like he wants to stay and have a talk but keeps thinking better of it.

'His name was Cas.' He bites his lip and looks down almost surprised at himself, like he hasn't said that name in years. 'His name was Castiel.' He taps the bar twice and walks away and out of Benny's line of vision.

Progress.

May 2013

'So I met this guy…'

Benny attempts to control his face as looks at Dean from across the bar. Picking up a glass, he starts polishing it while he waits for Dean to continue.

'His name is Adam, he's 25 like me. He's a Junior Accounts Manager like me, My marketing department is consulting with their marketing department on a product for the company he works for, and I had to meet with him the other day to discuss strategy.' Dean smiles, like truly smiles and it reaches his eyes in a way Benny has never seen before. 'He's awesome, man. He's like a guy, ya know? He drinks whiskey, loves old school cars and football. I just-' He cuts himself off and takes a drink of his beer. 'I'm happy, Benny. I haven't felt like this in years.' His smile widens as he traces the rim of his glass.

Benny smiles back at him. 'I'm happy for ya, Dean. Drinks or Pie to celebrate?'

'Please Benny, you know me.'

He laughs 'Alright then,' he pours two shots of whiskey 'Both it is.

The conversation Dean promised to have with Benny a year ago, forgotten.

September 2013

Falling in love with Adam was as easy as breathing for Dean Winchester. Four months in and Dean still could not get that shit eating grin off his face.

'I might be transferring to Chicago.' Dean miserably grumbled around his bottle of beer.

'Dean you are moving to Chicago, you got the promotion a week ago.' Benny grabbed the bottle from Dean's hand and raised it up over his head 'Jo! How many of these has he had?' Dean had arrived at the Roadhouse before Benny for their usual Tuesday Burgers, Pies and pool night.

'He's had four! Not to mention the shots before that.' Jo called out from behind the counter.

Shit. 'Dean, man you can't drink this much on a weeknight. You can't have a hangover at work tomorrow, unless you want to lose that promotion and be stuck with me the rest of your damn life.'

'I love Adam.' Dean slurs from across the table, he's leaning heavily against his back with his shoulders slouched in front with a defeated look on his face. 'I love him Benny.'

'I figured as much, brotha. You get all moon eyed when you look at him.' He sips Dean's beer.

'Ask me about him.'

'Dean I think I know everything I need to know about Adam-'

'No.' Dean cuts him off, waving his hand drunkenly as if trying to swat a fly. 'No. Ask me about him.'

Benny swallows. He knows what Dean is referring too, and not that he isn't interested it's just that Dean is drunk and would probably tell him anything right now and Benny isn't sure how he feels about that.

'Did you love him?'

'Yes.' The answer is immediate and filled with conviction, the look on Dean's face serious.

'Why did it end?'

'I fucked it up.'

Benny hums, even drunk Dean doesn't change the story.

'Would you still be with him if you could?'

Dean leans forwards onto his elbows and he makes eye contact with Benny. 'I would have stayed with him forever.' He slumps back against the wall of the booth.

'But not anymore?'

'I'm here.' He gestured to himself. 'I love Adam.'

'He broke your heart.' It is a statement more than a question.

'No.' He shakes his head. 'No, I did that all on my own.'

'Dean. Why now?' He questions his friend. 'I've asked you about this Cas guy ever since I met ya. Why are ya telling me bout him now?'

Silence.

Dean lets out a heavy breath. 'Cas lives in Chicago, or at least that's the last place I knew he lived. I don't want to go to Chicago. I love Adam but I can't run into Cas and see him happy with a boyfriend or a husband, I just-' He trails off, his emotions getting the best of him in his intoxicated state as he takes shaky breaths. 'I can't risk something amazing like Adam. I can't do that to him or to me. I won't survive it, Benny.'

Benny reaches across the table and pats Dean's arm. 'Chicago is a big city Dean, just like Berkeley. Don't psych yourself out.'

The next day Dean acts as if nothing had ever happened. Dean asks Adam if he'll move to Chicago with him, Adam accepts saying he'd follow Dean anywhere. The two plan a trip for the second week of October to check out some apartments and briefly familiarize themselves with the city.

October 2013

It's a cold day In Chicago.

'C'mon Cassie, come back to bed.' Balthazar pleaded in a tired voice.

'Balth I can't. I have an appointment with my professor to go over my thesis.' He pauses for emphasis 'This is important. This is my future.' Castiel attempts to put his shirt on, but only succeeds in putting it on backwards. Huffing out an aggravated breath he quickly tears it off his body and rights it.

'You'll do fine. Your thesis is fabulous. Just like your ass.' He laughs at his own cheeky comment and stretches his arms behind his head, catching fabric he brings it into his line of vision. Chuckling he throws the garment at Castiel who is frantically searching and muttering something about pants. 'So tonight, I was thinking dinner at Goosefoot again? It was so remarkable last time and William and Theodore have been asking for us to double with them again.'

'Have you seen my glasses?' Ignoring Balthazar's end of the conversation entirely, Castiel searches beside the bed in vain.

'Are you just going to ignore me?'

Sighing Castiel looks at the clock on the far wall; he did not have time for this.

'Balthazar. You know I'm not looking for a relationship. It's fun, the sex is great, I just don't need the full nine yards anymore...does that make sense?' He searches the British man's face. 'I'm looking for something fun in my life, not a partner. You knew that. I'm not feeling like we are on the same page with that anymore.'

Balthazar stands, boxer brief slung low on his hips. His eyes never leaving Castiel's face as he walks the few feet towards him. 'What happened to you? Why are you so broken?'

Castiel puffs his chest out 'I. Am. Not. Broken.' He grits through his teeth. 'I am driven. I have plans for myself. Why do I feel like we've had this talk before?'

'That's because we have and every time you put up your bloody walls and ignore everything I have to say. This may be hard for you to believe Castiel, but between all the strange boundaries and times of complete indifference you've thrown at me…I've fallen in love with you.' The admission hangs in the air.

Balthazar reaches down for the tan coat he gave Castiel all those months ago, picks it up and shakes it. He offers it to Castiel the same way he did that first night. Eyes wide Castiel steps into the jacket in much the same manner, turning to face Balthazar who flattens the lapels of the jacket.

'Your glasses are on the entry table. I know you always misplace them when you get frisky, so I moved them last night.' Balthazar's hands slide off Castiel's chest as he turns his back to Castiel. 'You'll be late. We'll talk later.'

'Balth-'

'Go Castiel.'

Staring determinedly at Balthazar's back, Castiel backs out of the room in a strange daze. Reaching the entryway he picks up his glasses and takes hold of the door handle, flinging it open and fleeing from the apartment he rushes down the hall to the elevator.

What is this feeling? Whatever it is he doesn't like it.

October 2013

Dean loves Adam in a way he never thought he could love someone. There is no way around it, Dean is happy. Years of self-loathing, working and drinking have led him to a whole new world of love.

They arrive in Chicago on a Sunday and immediately go out for burgers and beers. Flights make Dean nervous and bless Adam for picking up on that, even though Dean has never had a reason to inform him of that irrational fear.

Monday morning brings lazy kisses exchanged over breakfast in bed and an Old Clint Eastwood movie that Dean talks Adam into watching with him. As the day continues the two do some sightseeing and look through the paper at some apartment listings to look into the next day.

Tuesday has the two men smack dab in the middle of the city with a map in Adam's hands and the newspaper in Dean's hands as they attempt to find one of the apartment's on their list. Dean's eyes search the streets for some street name when his eyes stop.

Across the street, talking adamantly to a short redheaded woman is without a doubt the one and only Castiel Novak. Dean's heart clenches, it's been six years and his heart still clenches. He's purposefully avoided talking about him, thinking about him, saying his name, friends they once had in common. Honestly anything that reminded him of Cas he cut out of his life.

'Dean?' Adam grabs his arm, his brow furrowing 'You ok?' He looks in the direction Dean's eyes remain locked on but doesn't see what Dean sees.

His mouth is dry, why is his mouth dry? Castiel freaking Novak is across the street from him, wearing a tan coat that flaps in the wind. His hair is darker than Dean remembers, he's taller, he's bulked up and he dons a 5'oclock shadow. He's with a woman and he's laughing.

Dean wants to hear that laugh, hasn't heard that laugh in six years.

Unable to stop his body, Dean grabs Adam's hand and drags him across the street (safely) until he is but a few feet away from Castiel.

Castiel's back is to Dean at this point but the redhead seems to notice the two men approaching them and clears her throat.

'Hello boys, what can we do you for?' Charlie questions in a bubbly voice.

Castiel turns around and is met with a face he was never expecting to see again. He knows he looks wild, his hair's natural state is 'bed head' and he can only imagine he is mirroring the bewildered look that is plastered on Dean's face.

Moments pass.

Clearing her throat and clicking her tongue. 'I'm Charlie and this is my demented friend Ca-'

'Dean Winchester.' Castiel's voice is deep as he cuts Charlie off 'Finally made it out of Kansas I see.'

'Castiel Novak.' Dean laughs his name out. 'Right where I left you.'

A flicker of recognition passes over everyone's face.

Something happens neither was expecting to ever happen, they smile. Dean smiles at Cas and Cas smiles at Dean and for a moment it feels like it used to. Six years haven't passed and it's just the two of them.

Adam snakes his hand around Dean's bicep and extends a hand 'You're the famous Cas?! I'm Adam.'

And all at once the moment is broken, Dean and Cas aren't 18, they aren't madly in love, Dean is with Adam and Castiel is alone. Both men break eye contact and Castiel shakes Adam's hand.

'Anytime Dean mentions High School it's always Cas this or Cas that. It's nice to finally have a face to go with all the stories.'

Castiel forces a smile 'It's pleasant to know I'm spoken of so fondly, especially given the circumstances surrounding the ending of our relationship.'

'Relationship?' Adam rears his head back with a quizzical look on his face and turns to Dean.

Oh shit. Oh shit.

Dean's face pales 'I mentioned Cas and I dated, haven't I?' He rubs Adam's back awkwardly his eyes not leaving Cas' face, as if trying to soak up as much of him as he possibly can. Six years is a long time to go without seeing those blue eyes or those dimples he gets when he smiles.

'So what brings you two to Chicago? Vacation?' Charlie asks quickly, hoping to fill the awkward silence. Castiel mentally praises Charlie for picking up the conversation.

'Looking at apartments actually.' Adam declares, patting Dean's chest affectionately 'This big guy got a promotion that is moving him away from Sunny California to windy Chicago. So we are trying to find some good neighborhoods.'

'California?' Cas can't help but feel left out of some imaginary loop 'Since when?'

Dean shifts his weight a bit away from his boyfriend as Adam and Charlie launch into a long-winded conversation of neighborhoods and apartments they should look into.

'A map and newspaper dude, really? What year are you from?' Charlie scoffs as they break away from the other two.

'I did two years at KU then transferred to the University of California to finish out my marketing degree, which worked out in the end cause Sammy got into Stanford and moved there two years later. The plan was to move in together his sophomore year but he met this girl named Jess and long story short they are sickeningly cute and I expect to see an engagement ring as soon as they graduate.' Dean babbles and smiles thinking about Sam and Jess 'I got a job straight out of college and just stayed in California. It didn't even cross my mind to move anywhere else, why would I?'

The conversation flows from there, Dean learns Cas is still in school but doesn't have much longer until he graduates with his Masters and plans to apply to become a Professor's assistant or a Professor at a community college while he works towards a doctorate degree. Cas learns Dean is now a Marketing Accounts manager and yes it is as boring as it sounds most of the time. Dean expresses his concern on the weather of Chicago and Castiel teases him about being on the other side of the country for too long.

Dean can't stop staring at Cas, waiting for it to hit him in the stomach and leave him a sobbing mess. He almost wants it to. It's been six years but Dean still remembers being 18 and having his heart broken, he remembers crying himself to sleep for months at the loss. He expects this sinking feeling but instead he feels content, like he's finally able to breath for the first time in years.

Adam makes his presence known again by carefully tapping Dean's shoulder, Dean turns to face him and the look on Adam's face makes Dean believe this isn't the first time Adam has attempted to grab his attention. 'We should get going, it's almost 3 and we still have to find this apartment.'

'Of course, yeah sorry.' He quickly grabs Adam's hand and flashes one of his award winning Dean Winchester smiles at Castiel and Charlie who has also gotten Cas' attention as well. Now it feels awkward. Without Adam in his space he felt comfortable speaking with Cas, now he could feel Adam's eyes on him.

'It was awesome seeing you Cas.' His body twitches as if fighting the familiar urge to hug Castiel. 'I guess I'll be seeing you around.'

Castiel smiles. It's a sad smile Dean can tell because it looks just like the smile he gave Dean the last time they saw one another.

'We'll see, Chicago is a big city after all.'

Castiel and Charlie turn to leave at the same time Dean and Adam turn to leave. Neither Dean nor Cas turns around though they are both fighting the urge too.