As if I could pass this one up...
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Pam had been furious after Castiel had shown up to 'say goodbye'. And Dean could kind of understand that. And then she had been crying and upset, and that got him angry in turn.
And he let the angel know, of course. Even though he couldn't speak for Pamela and he didn't presume to - he had his own gripe with what had happened and he said so. Since, more or less, his own life kind of depended on things out of his control and into Castiel's and all.
But that wasn't important really, not after he went back to Pam's. Considering his own bright shining record of relationships (missing, more or less), he really didn't know what to say most of the time. He kind-of smiled and nodded at the right places. A couple of times he managed to twist things, especially ones that were directed by Pam at herself, in a way that made her laugh and relax a tiny little bit.
Even he could see she was frustrated, hurt, angry. So eventually he ended up pulling her in his arms, just to steady her a little. If she felt like hitting, she could slam her fists against him too, that'd be alright really. But the way her thoughts rambled that he could hear occasionally - it just didn't sound like the brightest idea ever to just let her slide down that way.
So he hugged her. When she eased a bit, sat with her on the couch, one arm still around her, letting her just... something. He wasn't what she wanted, wasn't who she needed, but at least she wasn't quite on her own. And it seemed wrong that somebody as strong and confident and amazing as Pamela Barnes felt so helpless, so self-depreciating, but he also got it, got that a part of that all had been a mask, and show she put on to make sure the world knew that it couldn't hurt her. Except, now it all deserted her, and that didn't make it any easier.
After a bit she kind of settled, just sitting quietly, thinking, and he didn't quite like the sound of silence like that. On the other hand, he coulnd't make up anything useful to tell her to distract her from it either.
So he opted for another thing, tipping her chin slightly from the downcast position it had taken and kissing her.
It wasn't a passionate, want-you-right-here-and-now-so-help-me-god kind of kiss. But it was honest, and appreciative. She was an amazing woman, and he did like her a whole lot, and that's all that mattered to that kiss. It was gentle but not light enough to be mistaken for fake; and it might not be insistent, but it was warm, and he didn't break it before she did.
Eventually, he just smiled slightly. "Keep your chin up, okay? See, life can still surprise you and everything."
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