They were in Chicago for Ben's baseball tournament. Lisa had told Dean the night they'd gotten there to go live a little. That was how he ended up in the Sunnyside Bar. There was nothing sunny about the place of course, except maybe the bartender who seemed to always be smiling and friendly.
"Pick a poison," she grinned as Dean came to sit in front of her.
"I'll just have a beer," he said quietly, not really feeling up to flirting or hell doing anything that he'd done at bars before. It was too painful; he didn't even know why he chose a bar to come to. Hell, he could've gone to a freaking gym or something. But no, something told him he had to go to the bar. So to the bar he went.
"Here ya go!" she announced setting the beer down in front of him with a smile before going off to the corner of the bar where two men sat, neither facing the door, and started talking to them. She seemed to know them pretty well which Dean thought was curious. When she returned curiosity won out and Dean decided he needed to ask her. For the sake of his sanity.
"Miss?" he said, getting her attention. Living with Lisa sure had taught him his manners that was for sure.
"It's Alli, what can I do for you?"
"Who-who are those two men over there?" Dean asked, and watched as Alli's face closed off.
"Why ya askin'? They aint done nothing bad. I can't honestly see either of them as hell raisers. Well, maybe the tall one, but the poor guy…I'm just glad he has a friend to look after him. He seems to need it." Alli said.
"I'm asking because a few months ago my-my brother went missing. I know-I know if he was back he'd let me know, I hope. But at the same time I think he'd probably stay away thinking that was best." Dean explained quietly.
"Well I can tell you their alleged names if that helps…" Alli trailed off.
"Alright. The shorter man's name is Cas? It's an unusual and unique name if you ask me…" Alli commented, nodding towards the man in question while cleaning a glass.
"And the taller man's name?"
"That's an easy one, he's really sweet. His name is Sam." Alli said with a grin.
"S-Sam?" Dean stuttered.
Alli nodded. "You gonna be ok?"
"I-I think that's-that's my brother and best friend." Dean rushed out.
"Really? Then go talk to them!" Alli encouraged.
"Ya think? But what if he's ignoring me cuz he's pissed or something?" Dean worried, pausing in the process of walking over there.
"Who cares? He's alive! You need to go give him a hug and chick flick the moment up!" Alli said exuberantly.
"You're right." Dean whispered swallowing.
Dean walked towards the two men, his hands shaking, heart pounding, looking back he saw Alli watching eagerly ignoring the customers across the bar. She nodded to Dean and made a 'go on' motion with her hand. Squaring his shoulders and sighing Dean strides with determination up to the table and looks the men right in the eye.
"Dean?" the face Dean'd never forget as long as he lived whispered, shock in his brown eyes, with his hair just as floppy and long as ever.
"Sam?" Dean choked out.
"Dean what are you doing here?" Sam asked getting up to give his big brother a hug. Dean returns the hug with so much force Sam actually can't breathe for a moment, but that's ok, because Dean's there.
Cas looked over at Alli and smiled. Winking she smiled back, stretched her wings and vanished. Still smiling Cas returned his attention to the reuniting brothers.
"I thought you were ya know!"
"How long ago? Why didn't you tell me? Sammy are you ok?" Dean fired off.
"A few months. I wanted you to enjoy your white-picket-fence life. I didn't want to interrupt your new life. And yes I'm fine!" Sam smiled, same old Dean worrying constantly.
"Good that's, good. You're an idiot; Ben'd love to meet a supposed dead man. Lisa's been asking about you too. Bobby's been looking for signs." Dean explained, still letting go of his brother.
"Cas found me in this…place out in Vegas a couple months ago. Some angel or something found me and reported it to Cas."
"Cas! Why didn't you tell me?" Dean demanded.
Cas' eyes widened in fear, "Dean, it was not the right time. I could not judge when the right time would be, but right after he came back was not it. I am sorry for prolonging your pain though." was Cas' well thought out answer.
Dean looked back to see what Alli thought of the entire thing, only to see an old man working the bar, Alli long gone.
"Did you guys see the bartender from earlier; she was in her twenties blond…?" Dean asked.
"Uh. Are you ok Dean? That's the same bartender that's been here all night." Sam said.
"Oh." and with that team Freewill left the building never to return.