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“I bet it takes no more than three years,” Charlie said, grinning at Sam over her beer. Sam snorted at that.
“No way. It’ll take at least eight. They’re both too dense. Especially Dean.”
“Why’s that?”
“Because our dad messed him up a lot with the internalized homophobia. Dean has always been an ally, but he has no fucking clue that he’s at least bi. I’m pretty sure he’s still trying to make dad proud even though he’s dead and was an asshole.”
Charlie hummed a little at that. It made sense from what she knew about their dad. She was glad the fucker was dead because she wasn’t sure she could keep herself from going after him for how he treated her two best friends/pseudo brothers. “How about we actually make it a bet? I win if Cas and Dean get together by the three year mark. You win if they get together after that. Sound good?”
“Yeah ok, I’ll take that bet. What does the winner get?”
Charlie just grinned at Sam.
~~~~
Charlie was winning this bet, that much she was certain of. She had the same certainty that Dean was bi, at least in regards to Cas. She’d seen those two just stare at each other and it was so very obviously pining and sexual tension. She was sick of it, and she knew Sam had to be even more sick of it considering how much time he was with them.
They just needed a little… push. A slight shove.
Dean specifically.
So, a number of months after she and Sam made that bet, she got to work.
And just hacked one of Dean’s phones.
It wasn’t hard, at least not for her, and she looked through a few things. Just to confirm that Dean did have feelings for Cas.
Bingo.
He’d searched up information on how someone knew they weren’t straight. Or at least not fully straight, because Dean did love women too. And he had good taste in women from what Charlie’d seen.
Back to her main objective.
After snooping a bit more, she decided that the best way to go about this would be to send a text to Cas through Dean’s phone and just… see what happened. Something that was flirty but not too out of the ordinary for a text from Dean.
Which meant reading a bit through their prior texts.
…
They already bickered like a married couple for sure.
There were also a few unsent texts that Dean probably hadn’t had enough service for them to be sent and were probably from times when he got drunk enough for any and all inhibitions to disappear, letting him fully accept that he loved Cas. Multiple mentioned how hot he thought Cas was.
So she’d take and edit together a few so she could use some of Dean’s own words.
Her fingers clacked over her keyboard as she created a message to send to Cas to let him know that Dean was interested. She knew Cas already accepted that he liked Dean and was likely just waiting to see if Dean ever felt the same.
Once she was satisfied with the message, she sent it through and leaned back in her chair. She’d do some research into supernatural cases and plan her next con or LARPing trip while she waited for everything to unfold.
~~~~
Cas got a message on his phone while he was in his room in the bunker. He didn’t really sleep much, but he appreciated having his own space. He pulled his phone out, curious who texted him since he didn’t really text much. He’d only more recently gotten the hang of it.
It partially involved Sam and Dean explaining texting slang.
Gabriel texted him a lot using slang that the two brothers didn’t understand either.
He saw it was a message from Dean, which was a bit odd since he was at the bunker too, but not overly uncommon.
Then he opened the message and felt his cheeks heat up.
Dean had sent him
You’re so hot Cas and I can’t stop thinking about you. I really like you.
Dean… liked him back?
He’d realized he liked Dean a while ago, but he didn’t say anything because he didn’t want to make things awkward or have Dean feel pressured to reciprocate. Especially since he wasn’t sure whether Dean only liked women or not.
Apparently, he did not only like women and had developed feelings for him.
Smiling, Cas typed out a response and sent it to Dean, hoping this went the way it seemed to be going in his head.
~~~~
He’d been cleaning his weapons after their most recent hunt, making sure they were all clean of gunk and whatever the monster of the week had gotten on them and also making sure everything was in working order.
Would royally suck if one of his guns jammed during a hunt when he’d need it.
He heard his phone ping with a text, but waited until he was finished with the weapon he was currently working on to see who’d messaged him.
After putting down what he’d been holding and wiping his hands off on a nearby towel, Dean picked up his phone and unlocked it after seeing that Cas had messaged him.
His eyes widened.
Glad to know you share my feelings. Now you know why I can’t keep my eyes off you. I’d like to know what your thoughts are about Dean ;)
Trying to find out what happened, Dean scrolled up to see that he’d apparently sent a text to Cas and it looked like one he’d written while drunk before that failed to send. He wasn’t sure why it all of a sudden sent now but he had more important things to worry about.
Like what to do in response to this text.
He wasn’t going to talk to Sam about it because he’d never stop teasing Dean over it no matter what the outcome was. Dean was not going to him about his possible bisexuality now or ever.
As he thought about it, he realized the perfect person to talk to about this.
Charlie.
She wouldn’t make fun of him for this little crisis. She’d never made fun of him when he helped her flirt her way past a male security guard after all.
He pulled up her contact and called her, waiting a few moments for her to pick up.
“Dean, what’s up?”
“I have a problem.”
“What sort of problem?” she asked, sounding a little concerned.
“It looks like a text I wrote a while back while drunk somehow got sent to Cas and he sent back a flirty text and I have no idea what to do.”
There was silence over the line for a moment or two.
“Do you like him back?” she asked, causing Dean to think for a moment in return.
“I-I think I might. I haven’t entertained the thought too much before now.”
“Why haven’t you? I’ve seen the way you two look at each other when I’ve been by. I may not be into men, but I could easily tell that there was something between you two.”
That made Dean pause. Had he really been looking at Cas like that? Had Cas really been looking at him like that?
Oh God, did that mean Sam knew?!
“I mean, we’re not in the best line of work for relationships anyways, but I just never assumed that I’d be…”
“Bisexual?”
“Yeah… I mean I’ve had some fleeting thoughts but nothing I ever thought about too much.”
“From what you and Sam have told me about your upbringing, I’m guessing it had something to do with your dad?”
He tended to forget how even other hunters seemed appalled at how he and his brother were raised. And how they’d always get this knowing look in their eyes like they’d just figured something out. This tracked.
“Yeah, he wasn’t really the most… open about people who weren’t fully straight. I mean, I never really talked with him about it so I don’t know his exact feelings, but I also don’t think he’d be too thrilled that I might have feelings for an angel, too. Especially since most angels are dicks.”
“Hm, there’s that too. So, do you like Cas? It’s not like your line of work would get in the way considering he’s become a hunter or hunter-adjacent with you.”
She definitely had a point there.
“I never really considered that…”
“Plus, dude’s an angel so I think he can take care of himself pretty damn well.”
Another point for Charlie.
“...Think I should respond?”
“I think you should go for it. If you’ve nearly sent him texts before about liking him or whatever it is you sent, then those feelings are definitely there. Who knows, this might be really good for the two of you.”
“Thanks Charlie.”
“Anytime. Let me know how it turns out. Later bitch!”
Dean chuckled and ended the call, staring at the text Cas had sent for a moment before writing out a response of his own.
Why don’t you come to my room and we can talk about it?
Dean felt like he couldn’t breathe for the few moments it took Cas to read the message and then show up at his door, forgoing responding through text and just responding in person instead.
“I’d like that, Dean.”
He smiled in response and invited Cas in, closing the door behind him so his nosy little brother wouldn’t hear or see this conversation.
Sam wasn’t going to know a thing until he was ready.
~~~~
It took a few hours for her to hear back from Dean.
We’re going to try dating. Thanks for your help, Charlie. I’m not telling Sam yet though.
She smiled, knowing that Sam already knew they had feelings for each other and would likely be able to tell they were in a relationship within a few days. She was going to wait to see if he called or messaged her before reaching out herself. It would be better if Sam reached out to tell her she won the bet rather than her telling him.
And she didn’t have to wait long, just like she thought.
It took nearly a week, but Sam must’ve noticed something because she got a call from him.
“You win the bet, Charlie,” Sam told her, sounding a combo of annoyed and happy. Likely annoyed she won but happy that Dean was happy. And happy for himself for not having to watch them pine anymore.
“They’re really together?” Charlie asked, feigning ignorance of their current relationship status.
“Yeah, they are. I don’t think Dean knows I know, but I saw them kissing the other night when they must’ve both thought I was out of the room. I don’t know how new this is but I’m not letting Dean know I know. I’ll let him tell me on his own.”
“I fucking knew it wouldn’t take them longer than three years! Not when they’ve been pining for too long already! Don’t worry, I won’t let Dean know you know.”
“Thanks Charlie.”
“Now about my prize…”