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"Dean, I need to talk to you about something," Sam said. The look on his face told Dean that his brother had worked himself up to having a Talk and no amount of avoidance on Dean's part would convince him to let it go.
Dean sighed and poured himself a small measure of scotch before he sat down next to his brother. "Okay, shoot."
Sam raised his eyebrows. "That easy?"
"Limited time only, dude. Spit it out. And don't sugar-coat it."
"Alright, well – I think Cas loves you."
"Oh." Of all the conversation topics Sam could have come up with, Dean hadn't been expecting that one. Or, at least, he had been expecting it a few years ago and when Sam never said anything – not even after Purgatory – Dean assumed he never would. "Well, yeah."
Sam frowned. "I'm not sure you're getting me. I think Cas is in love with you."
"No shit, Sherlock. How did you work that one out?"
"I'm serious, Dean – wait, what? You know?"
"Kinda hard to miss, isn't it?"
San looked stunned. "Wow. Uh, I thought you would take more convincing. I had a whole stack of evidence to take you through, I prepared arguments and counter-arguments…"
"I do have eyes you know."
"Uh, right. Well, don't freak out or over-react or anything, but uh – I think that you might have feelings for him too."
Dean shrugged. "I guess. What's your point?"
Sam goggled at him. "You can admit it just like that? Aren't you going to have… I don't know, a big gay freak out or something?"
The time for that had been and gone. "I figured out that I was bi when I was a teenager," Dean admitted. There had been a boy at school, a few stolen kisses behind the bleachers, a few ignorant bullies, a dance they almost went to together wearing matching tuxedos, and then Dad had come home and moved them to a new town. Dean never saw the boy again. In the long run, it was probably for the best. "I knew Dad wouldn't like it so I never brought it up."
Sam looked hurt. "You could have told me."
"I thought you would probably be okay with it but you were already butting heads with Dad and I didn't wanna risk giving you another reason to leave."
"Dean…"
"Seems you worked it out on your own in the end anyway. And if you're trying to play matchmaker between me and Cas it can't bug you too much."
"It doesn't bother me at all. You're my brother, Dean – I don't care who you're attracted to or who you fall in love with. I just want you to be happy."
Dean gave a wry smile. "Good to know. And thanks, but I don't think that's ever gonna happen."
"What?"
"My 'happily ever after'."
"Why not? I thought we just established that Cas likes you and you like him, and that I would have no issue with you two getting together. So what's the problem?"
"It is never going to work, Sam."
"How do you know until you try?"
"Because I'm not an idiot! I know our family's track record when it comes to relationships and it is not good, Sam. It always ends in someone dying or leaving or turning traitor or winding up so friggin' damaged that they would be better off dead."
"It won't be like that with Cas."
"You can't know that. Cas has already died four times since he met me – what do you think dating me would do to his life expectancy? And I don't even know how many times I've carked it, but I do know for a fact that I'm far more likely to die bloody than of old age. So what's the point of starting anything?"
"Dean-"
"Even if, by some miracle, we don't die in the immediate future, do either of us really strike you as relationship material? He's an emotionally stunted angel who can barely take care of himself, and I'm an alcoholic with more issues than brain cells. Besides, we fight enough as friends – if we threw relationship troubles into the mix we'd probably kill each other."
"Isn't the fact that you're still friends after everything you've been through proof that you're strong enough to make it through anything?"
"I don't know why Cas has stuck around this long, but there's nothing keeping him here. He's going to leave eventually. Everyone else has."
"I'm still here."
"You're family."
"So is Cas. And if you asked him to stay, he would."
Dean dropped his gaze. "I know," he said quietly. "That's why I can't. He's given enough for me. He deserves better."
"He deserves to be happy. You both do. And if you would just let yourselves act on those feelings you've been trying so hard to ignore, you could be happy."
"Cas would be better off finding some nice, normal chick to settle down with."
"There isn't a girl out there who could understand him the way you do. Besides, what makes you think he wants to find a girl?"
"He has hooked up with chicks before."
"You mean that hooker you set him up with?"
"I mean Meg and Daphne, and that reaper he slept with. He even gave it a shot with that woman from the gas n sip. He's trying. I'm sure with a little help he'll be able to find a match. Someone sweet and gentle with a soft spot for lost puppies."
"I think he would rather be with you."
"That's not an option."
"So what? You're content to let the guy you have feelings for go off and marry someone else?"
"If you love them, let them go, right?"
Sam stared at him. "You love him?"
Dean hastily tried to back pedal. "I didn't say that."
"Oh my god."
"Sam-"
Sam punched him.
Dean reeled back, a hand flying up to comfort his jaw. "Ow! What the hell-"
"You're an idiot!" Sam seethed. "You're in love with your best friend but you won't give it a shot because you're scared it won't work out?"
"I'm being smart, Sam. I'm not going to put my heart out there to be stomped on and run over and shattered into a million pieces when some monster comes along and rips Cas's head off."
"And you think that distancing yourself would make losing him hurt any less? Dean, the hooks are in, you're lost already. You'd be a wreck if Cas died, period. But what do you think you would regret more? Making the most of every day that you have with each other or never telling him how you feel?"
Dean fell silent.
"I loved Jessica," Sam said. It caught Dean's attention; Sam had not mentioned her name in years. "I still miss her. It still hurts. But even if I had known how it would end, I wouldn't trade a single second I had with her for anything. It's true what they say, you know. Better to have loved and lost."
Dean looked away, unable to bear the grief in his brother's eyes.
"Jess is gone now. I'll never have another chance to tell her that I love her. But it's not too late for you. Don't wait until it is."
Dean didn't know how to respond.
Sam reached out and squeezed his shoulder. "Just… promise me you'll think about it."
Wordlessly, Dean nodded.
Sam smiled sadly and left him alone.
Dean sat there for hours before he slowly, hesitantly, pulled out his phone. He scrolled down the contacts list, took a deep breath, and pressed call.
"Dean?"
"Hey Cas…"