Anna Milton is sweet, and fragile, just a nice girl from a small town going to school for journalism. She also happens to hear the voices of angels, and if that-a perfectly nice, ordinary girl who never hurt anyone being driven over the edge by a constant line into Angel Radio-doesn't prove that God had a sick sense of humor, Dean wonders what the hell else would do it.
Of course, a day and change later Anna turns out to be a fallen angel, and through the shock of having her worldview rocked yet again, Dean thinks she may like her more for that small detail.
What she doesn't understand is why on God's green Earth, no pun intended, Anna would want to have anything to do with humanity. For all that Dean's always waxing truculently defensive about her own species' right to survive, her first-hand experience with life has been less than stellar: blood, death, darkness, and pain. Why would an angel want to subject themselves to all of that?
She should probably have expected, after her limited interaction with Cas and his dicks-with-wings-on-parade band of brothers, that Anna's approach would be obnoxiously zen and glass-half-full.
"There's loyalty," Anna tells her. "Forgiveness."
"Pain," Dean counters.
"Chocolate cake," Anna shoots back.
"Guilt." Dean thinks she has it nailed on that one.
"Sex," says Anna. Dean tries and fails to suppress a grin.
"Yeah, you got me there," she says, but her heart's not quite in it. Anna must sense that, because she steps closer, looking up at her, face earnest.
"I mean it. Every emotion, Dean. Even the bad ones. It's why I fell." She looks away, wistful. "It's why I'd give anything not to have to go back. Anything."
"Feelings are overrated, if you ask me," Dean says.
"Beats being an angel." The bitterness in Anna's voice is surprising, sharper than anything Dean's seen from her so far. She still looks so small, so pale and breakable. It's hard to believe there's an ageless being of pure energy and power living behind her eyes.
"How's that possible?" Dean questions her, really wanting to understand. "You guys are powerful, and perfect. You don't doubt yourselves, or God, or anything."
"Perfect," Anna scoffs. "Like a marble statue. Cold...no choice, only obedience." Anna turns her head to pin Dean with her eyes, an unspoken challenge in her tone. "Dean, do you know how many angels have actually seen God? Seen his face?"
Dean shrugs. "All of you?"
"Four angels. Four. And I'm not one of them."
That brings Dean up short. "That's it? Well then how do you even know that there is a God?"
"We have to take it on faith," Anna says. "Which we're killed if we don't have."
Dean doesn't know what to say to that. She feels like an ignorant child, talking about how bad she's got it to someone who's lived an existence longer than several generations of her family, under threat of death for not believing hard enough. Anna continues, seemingly oblivious to Dean's apologetic discomfort, pouring her frustration into the silence between them.
"I was stationed on earth for two thousand years, just...watching...silent, invisible. Out on the road, sick for home...waiting on orders from an unknowable father I can't begin to understand."
And suddenly, they're on common ground. Dean suppresses a mirthless laugh; it isn't funny, not really. It's ironic, though, that she of all people could look at an angel and say to her "I know how you feel."
She hates it when people say that to her, even when it's true. So she stays quiet, just listening.
Dean wants to scream, or punch something, or both. She forces herself not to clench her fists too tightly around the book she's holding; it's old, and would probably crumble or tear under that kind of pressure. But her hands itch with the kind of restless anger best exorcised by breaking things. They've tried; they've done everything they can do...but they can't save this one, this angel that wanted to be a normal girl, who saw something beautiful in the mess that was humanity...
"Dean." Anna's voice pulls Dean out of the angry swirl inside her brain. She breathes deeply through her nose once and tries to school her expression into something supportive and reassuring before looking up to see Anna's slight frame moving toward her in the blue darkness.
"Hey," she says, "holding up okay?"
"Trying." Anna's voice sounds strained, but there's a calm set to her face that Dean doesn't like. She wonders if Anna's going cold already even without her Grace, the memory of what she once was turning her slowly back into an emotionless statue.
"A little scared, I guess," she admits then, and Dean tries not to take a breath of relief. "So, um...Dean. I just wanted to thank you."
"For what?" Dean asks, incredulous. She hadn't been able to actually do anything.
"Everything," Anna shrugs, looking out and down at nothing in particular. "You guys...you didn't have to help me-"
"Hey," Dean interrupts, unable to listen to any more. "Let's can the 'thanks for trying' speech, alright? Don't thank me for helping you when I...we couldn't..." she trails off into silence, unable to finish the thought. She's not even sure who the good guys are anymore, but this feels like a battle fought on two fronts, and lost. She's not going to be able to bury this one, not like the others she's failed to save. She's going to dream of Anna's face, she knows it. She's never going to forgive herself for losing this particular fight, and she doesn't even know why it matters so much more than the others. She doesn't think it should, and that just makes it all even worse.
"I don't know," Anna says, sounding very small. "Maybe I don't deserve to be saved."
"Don't talk like that," Dean tells her, frowning. Anna looks up at her, the calm mask from before chased away by uncertainty and sadness, and fear.
"I disobeyed. Lucifer disobeyed. It's our murder one, and I knew it. Maybe I gotta pay."
"Yeah, well, we've all done things we gotta pay for," Dean mutters, not quite looking her in the eye. What is she doing, breathing the same air as an angel? In particular this angel, who is everything Dean could have ever imagined angels to be, back when she believed they were just nice stories people told each other for comfort.
"I have to tell you something, Dean," Anna says after a moment, mood abruptly shifting back to that discomfiting calm, but with a hint of something else...concern, maybe? "But I don't think you're going to like it."
"Okay," she says warily. "What?"
"About a week ago, I heard the angels talking. About you...what you did in Hell." Dean stiffens, mouth open to cut Anna off right there, but she plows on ahead without giving her a chance.
"Dean, I know. It wasn't your fault. You should forgive yourself." She's stepping close, right up into Dean's personal space, looking up at her with cool blue eyes that promise forgiveness Dean doesn't think she deserves. Not for this.
"Anna," she husks out around the sudden lump in her throat. "I don't...I don't want...I can't talk about that."
"I know," Anna says softly. "But when you can, you have people that want to help. You're not alone, Dean. That's all I'm trying to say."
And then Anna's leaning up, and in, pressing a soft, sweet kiss to Dean's lips that Dean is almost too surprised to return. It only lasts a second, but when they pull apart Dean can feel the warmth rising in her cheeks.
"What was that for?" She has to ask.
"You know," Anna says, almost coy. "Our last night on Earth and all that."
Dean can't suppress the small grin at that. "Oh, c'mon," she says indignantly. "You're stealing my best line."
Anna returns the smile and leads Dean by the hand, around to the back door of the Impala. Dean goes willingly, and without thinking too hard. Sure, Sam or Ruby might wander out and see them. Let 'em, Dean thinks a little savagely. She's not going to let it stop her, not now...not when it really could be Anna's last night on Earth. Hers, too, for that matter, if the angels make good on their threat.
Dean shuts off her brain and just lets herself feel, and what she feels is that maybe Anna's right...maybe this, these parts of being human, the moments of closeness and warmth and peace...maybe they're worth it after all.