It takes a bit of persuading, but Dean's publicist reluctantly decides to get him in contact with Meg Masters. They'd met once before at the Met Gala a few years back, shortly after Angels and Demons came out. They only spoke briefly -- Meg was with Castiel at the time, and Dean was a little too focused on finding a one night stand to talk for long. They'd attended the same events a few times since then, but they hadn't seen each other at any of them.
If it hadn't been for Castiel, they probably wouldn't have spoken ever again. With Meg into the acting side of LA and Dean on the musical side, they don't tend to run into each other much, after all. But she dated Castiel, and now Castiel's stolen Dean's girlfriend. What better PR stunt than to spread the rumor that Dean turned around and took his ex?
Of course, this was all riding on Meg's thoughts on the feud. Castiel has already admitted that their relationship was fake, and that he and Meg are actually friends again. Dean almost expects her to turn him down out of loyalty to her friend, but, as luck would have it, she seems overjoyed to be a part of this.
Dean meets her at a very expensive, very fancy restaurant in LA. They barely know each other, and Meg turned down the idea of getting a ride from America's biggest fuckboy -- or, at least, not on the first date, though Dean assumes that this last part was a joke. He makes it to the restaurant before her, but she sits down across from him after just a minute or so. Dean had thought he was looking rather dapper in his dress shirt and snazzy black pants -- a rare departure from his flannel and blue jeans -- but Meg looks even more stunning in her long, tight dress with a remarkably low cut top. Maybe she really is gunning for a second date, and honestly, he might be on board with it if he gets to look at this.
"A bit petty, don't you think?" Meg asks as she sits down across from him, a small smirk on her face.
"And what would that be?" Dean inquires, forcing himself to look her in the eye and not... down low.
"Cas stole your girlfriend, so you gotta steal his?" Meg shakes her head. "Tsk tsk, Dean. I thought you were above that."
"All's fair in love and war," Dean says with a small shrug.
"And which, pray tell, does this fall under?"
"I think it's a little bit of both."
Meg shakes her head, amused. "Oh, Dean. What are we going to do with you?"
"What would you like to do with me?" Dean asks with a wink.
"Ooh, I like you," she says with a sly smile. "But I have to ask. Did you really ask me here to flirt? Because that's an awful lot of trouble to go through for someone you've barely met."
"No, I didn't," Dean admits. "Though I am enjoying it immensely."
"Well, we can always cycle back to it at the end of the night, how about that?" she suggests. "Now, why did you really want to talk to me? I take it it wasn't just for the cameras."
"No, actually, I had a couple of questions that I probably shouldn't be asking," Dean tells her.
Meg raises an eyebrow. "Did you, now? Well, those are my favorite types of questions to be asked. What's on your mind, Dean?"
"It's about Cas," Dean begins. He pauses, giving her a moment to cut him off if she's sworn to secrecy. He doesn't want to ask anything if it'll make her uncomfortable, and he certainly doesn't want to ask if it will make its way back to him.
"Oh, don't tell me he really broke your heart." Meg shakes her head at him. "If I know Clarence -- and I do know him -- he doesn't care about Jo any more than he cares about you, me, or that waiter over there."
Dean raises an eyebrow. He'd assumed, of course, that Castiel didn't think of Jo as any more than a friend, but he had still thought that he looked at her as a friend. Meg seems to think otherwise. He debates questioning her, but decides against it. It's probably just some weird joke, like the fact that she called him Clarence. She's done it before in old interviews with the two of them that Dean may or may not have been watching, too, and no one seemed to question it. This is just who she is, apparently.
"Actually, Cas and I are pretty good friends," Dean tells her. She seems to have picked up on the fact that Jo and Castiel's relationship is fake, so she might as well find out that Dean doesn't care about it.
"If you managed to be 'pretty good friends' with him, I'm gonna want some proof," Meg says. "He's a great guy, but friendships are not his forte."
"What? Aren't you guys friends, though?"
"Yeah, in theory," she says with a noncommittal shrug. "I'm probably the closest to a friend of his you'll find, if that's where you're going with this, but I can only initiate so many conversations. He's a pretty lonely guy."
Dean frowns. He'd definitely gotten the impression that Castiel didn't talk much, but he'd still assumed the guy had friends. He makes a mental note to text the guy more often. He likes talking to him as it is, but knowing he doesn't have many friends is a lot more incentive to try to become one. The life of a celebrity is pretty lonely as it is, despite what the parties may show. He can't imagine not having his friends by his side throughout all of it.
It's an easy segway into his question, though, so points for that.
"What about family?" Dean asks. "Has he ever mentioned them?"
"Well, yeah, he --" Meg cuts herself off mid sentence, thinking.
That's about all Dean needed to hear. He'd been wondering about Castiel's family for a while, but seeing him get all flustered when Jo mentioned them finally convinced him that he had to know. He'd tried googling it not too long ago, and he couldn't turn up anything. Even wikipedia's "Early Life" section was practically empty. It didn't even list where he was born, never mind his parents or siblings. Meg was his last ditch effort, and that clearly didn't pan out. His family really is a mystery, apparently.
"I don't know," Meg says finally. "Off the top of my head, I don't remember him mentioning them."
All Dean can think to say is a simple, "Huh."
"Well, what were you gonna ask about him before I so rudely interrupted?" Meg asks.
So she doesn't realize she just answered his question. It must have looked like he was just asking what she meant instead. He could -- and probably should -- admit that she just told him exactly what he was wondering, but he's still slightly paranoid that she'll tell him, and he can safely assume that Castiel would not be happy to hear that Dean was asking about his family. Instead, he goes with a safer option.
"I was just wondering if he was always so reserved," Dean lies. "I wanted to make sure it wasn't something I did wrong."
"Oh, don't worry about that," Meg assures him. "I'm half convinced he loves everyone and doesn't know how to tell them, and I'm half convinced he hates the human race for reasons unknown."
"Awesome, thank you," Dean says. "That makes me feel a lot better." That part isn't entirely a lie -- he was definitely hoping Castiel was always like this, because he didn't want to think he'd done something to rub him the wrong way.
"Is that it?" Meg asks.
"That would be it," Dean replies.
"Then I guess we can get back to the flirting, huh?"
Dean chuckles. "If that's okay with you, it is more than okay with me."