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Dean often told Sam to get a backbone and stand up for himself. Then he’d turn around and call Sam selfish when he did. Given those two choices, Sam preferred being spineless to being selfish, when other people’s happiness was on the line.
Sam and Meg had been best friends since they were in first grade. Cas had joined them at the start of junior high. Now the three of them were in their senior year. They’d all applied to the same colleges, and they’d make their decision based on who got in where. Not that they were necessarily all going to the same school, but if there was a good way…
That was all good and well, but Sam discovered something accidentally. Cas dropped his backpack to go pull bullies off Kevin, again, and once Sam and Cas had gotten him safe, Sam helped Cas pick up everything. He hadn’t meant to keep a paper, but he hadn’t spotted it by the trash can until after Cas was gone. He hadn’t meant to read it, but he had this annoying thing where if he glanced at writing he couldn’t help reading a few words, and when he saw the phrase “in love with you”, he couldn’t stop himself from reading the whole thing. It was a love letter to his dearest friend. As bad as Sam wanted it to be to him, he was convinced it was for Meg.
Then he overheard Meg talking to her friend Ruby about how beautiful her best friend was. It was both heartbreaking and a relief when she mentioned the beautiful blue eyes. Heartbreaking, because she was talking about Castiel and not him, and he loved her. A relief, because Cas was in love with her, too, and at least two out of three of them could be happy.
He tried, subtly, to get the two of them together. Talking about what an awesome boyfriend Cas would be when he and Meg were alone. Talking about what an awesome girlfriend Meg would be when he and Cas were alone. Although they both agreed enthusiastically, neither of them seemed to be willing to do anything about it.
Then, one day, Sam had a brilliant idea. They were over at his house brainstorming ideas for an English project. “You know what would be really fun?”
Cas looked skeptically at Sam. “What?”
“Our project is about the trope of fake dating, right?”
Cas and Meg looked at each other. “Yeah…” Meg prompted.
“So for 24 hours, two of us pretend to date! Then we have a real-world example of the trope to compare to the various literary examples we find.” Most of the time, fake dating led to real dating in literature. He just had to hope it would work in the real world as well.
“Sounds good, but… which two?” Cas asked, looking between Meg and Sam hesitantly.
Sam smirked. “You two. You’re the actors.” Not that it would require acting, but still.
“But…” Meg started to protest.
This was the other part of Sam's plan. Meg and Cas were going to need convincing. “Unless you’re scared. We can make it a dare. Dean?”
Dean didn’t bother to leave the couch where he had his head in his girlfriend Cassie’s lap. “Meg and Cas, fake dating for an English project, dare from Sam. Witnessed.”
“Second witness,” Cassie added, not even looking up from gently scritching Dean's hair.
Cas and Meg looked at each other. Sam smirked. They’d never refuse a dare, not when there were witnesses.
A week later, the three of them once again met at Sam’s house for dinner and English project work. “Well? How’s it going, you two?” Sam asked, pulling out a notebook where he’d diligently written his ‘observations from the outside’. His own observations, talking to various friends, he’d even asked their English teacher for her input.
“Sam, can… can we talk to you?” Cas said. “It’s not about the project, but it’s kind of… related.”
“Sure.” Here it came. The plan coming to fruition. Part of him was overjoyed. Part of him was about to be in the worst pain of his life. “What’s up?”
“We did your dare, but there was a good reason I’d never asked Meg out,” Cas started. He stared at the table. “I suspect you’ve guessed somehow that I care for her a great deal. The thing is, there’s someone else I care for just as much, and I thought he liked Meg, too. It didn’t seem fair to Meg to ask her out when I wasn’t sure what I wanted, and it certainly wasn’t fair to ask her out when I didn’t know what I wanted but someone else did.”
Meg kicked up her feet, resting them on the table. “It’s pretty much the same for me. Ruby thinks I’m an idiot, that I should just flip a coin or whatever. I care too much to do that. Cas and I talked this through last night, and you know what it turns out? Turns out that we’re both looking at the same other person, and both of us would swear he’s into the other one.”
Cas leaned forward, bracing his arms on the table. “So it seems like the best thing to do is go straight to the source.”
Sam tried to make sense of it. He failed. “What? Who’s the source?”
Meg reached out and punched his shoulder. “You are, you goober. Cas and I like each other. We also both like you. If we’re both right about you, then I think we’ve got a nice obvious solution. If we’re not… well, we’ll figure it out.”
“I… what?” Sam stared at his notebook, trying to sort through this. “You both like me?”
“Yes,” Meg and Cas said in unison.
“And each other.”
“Yes,” they chorused.
Well then. Sam raised his eyebrows. Only one more thing. “You don’t think jealousy will be a problem?”
“It hasn’t before,” Cas said.
Meg smirked at him. “Don’t even try to tell me this ‘project’ wasn’t your crazy scheme to get me and Cas together.”
Sam blushed and ducked his head, but he was smiling. “It was. In my defense, it worked, didn’t it? Just not like I’d expected.”