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They met Anna during the apocalypse, or rather the would-be apocalypse. Sam was getting over the guilt of letting Lucifer go free by going on a date with some girl, Emma, leaving Dean, Cas, and Jo to do all the dirty work, at least for today. They were asking around, about how to kill Lucifer, or put him back in the cage, or really any way to stop him when they found Anna, quite on accident. Their questions led them to a very-unhelpful doctor. They were going to leave when Anna, in all her pale glory, walked right by them, talking to the slender nurse by her side.
"But you have to believe me! Lucifer is out of the cage!"
"Sure, honey. I'll take you to your psychiatrist tomorrow. Did you take your meds today?"
Dean immediately latches on to what the girl has said.
"Excuse me, " Dean butts in. "FBI." They hold up their fake badges. Cas holds his upside down and Dean corrects it with a sigh. "He's new," he mouths. "We'd like to talk to her."
"No idea why. But she's all yours. Visiting hours end at 8, but she's allowed to leave the grounds today, as long as she takes her meds and wears an ankle bracelet so we can make sure she's okay."
"Thank you, Ms. Evelyn," Cas states, reading off of her nametag.
She whispers to the three of them. "Anna's schizophrenic. I don't know what you want to talk to her about, but she hears the voices of 'angels' in her head, so note that any information is unreliable."
"All information is unreliable." Cas sasses without even realizing it.
"Cas, be nice," Jo retorts.
They walk to Anna's room to interrogate her. Dean pats Cas' arm in his awkward,"manly" manner. Though if Cas had his way, they'd be holding hands right now, or making out like teenagers, even though they were in the company of Jo, and a stranger. They look into each other's eyes for a few moments too long.
"Please. More eye-sex." Jo says sarcastically while Dean blushes. Then her train of thought is derailed when she sees Anna. Her whole life, she's considered herself to be straight. But one definitely does not think those kind of things without a sexual connotation. Long flowing red hair, deep brown eyes and a gorgeous figure that Jo wants to wrap around. Yup, definitely not straight. Anna gives Jo a shy smile, but looks at Dean and Cas waringly.
"It's Jo you need to be scared of," Dean jokes. Anna giggles and Jo lightly punches Dean's arm. "Idjit," she mutters, reusing her surrogate father's favorite word.
"Why are you here?" Anna asks nervously.
"We need to know about those voices in your head."
Anna's jaw tightens. "I don't want to be mocked again, not any more. I don't want to be told what I feel, what I know, isn't real. Just let me be."
"We won't mock you," Dean says softly.
"If you don't want to talk to them, pretend they're not here and just talk to me." Jo tells her. "If there's anyone who understands being mocked, it's me. I was the freak with a knife collection. Only place I belonged was with my parents." She laughs a little, to hide the bitterness and pain behind her words.
Anna has tears in her eyes. "Sorry."
"Don't be." Jo protests. "Not your fault."
Jo places her hands on Anna's wrists as she sits down in a conveniently located chair. "Begin when you want to." She attempts to make the gorgeous woman feel at ease with them.
"I hear these voices, in my head. No, they don't command me to kill or steal, they're not evil. They're angels. It's almost like I"m overhearing a conversation or listening to a radio. Lucifer was freed from the cage. The angels, they want Michael and Lucifer to duke it out. If Michael defeats him, then we all get paradise." She concludes. Dean nods to himself.
"Thank you for your invaluable help," Jo says softly.
Cas turns to Dean and Jo. "Based on the information provided, Anna is a fallen angel who is still able to listen to angel radio." Cas states. "She reminds me a bit of Anael, a rebellious angel I once knew."
"That's me." Anna says. "It sounds right."
Jo snorts. "Figures."
"What figures?" Cas cocks his head and Dean gazes at him adoringly.
"That I would have a crush on a fallen angel who's way out of my league." Anna's forehead crinkles. "Out of your league?" "Unrealistic, way too attractive." Anna blushes. "What's your name?"
"Jo. Joanna Beth Harvelle."
"Pretty name for a pretty girl."
Dean coughs. "Uh, could you stop flirting? It's awkward. I mean, unless you want to make out. Lesbian action is hot."
"Dean, what is it about lesbians that you find so attractive? is it the same sex relationship? do you desire one yourself?" Cas asks Dean.
"It's awkward when you two flirt. Unless you want to make out. Totally okay with that." Jo snarkily comments.
Dean glares at his friend/almost sister.
Anna gestures to Cas and Dean. "You two make a lovely couple."
Cas smiles his adorable half-smile and replies," Thank you," while Dean protests, "WE'RE NOT DATING!" "We will be," Cas smirks and leans in to kiss Dean. Let's just say the kiss was not entirely unwelcome. They pull apart and Dean leans in for another kiss. Then he pauses.
"Here are the keys, Jo. Take care of Baby. If you hurt her, I'll hunt you down. Sam's out. Me and Cas are going to," he doesn't complete the sentence, as Cas has already whisked them away.
Knowing Sam, he's probably having sex with Emma in a random hotel right now, and Dean and Cas have probably made similar plans.
"I'm alone and available, in every sense of the word." Jo winks. "Staying in or going out?"
"Doesn't matter," Anna giggles.
**
Team Free Will (Which includes Dean, Sam, Cas and Jo, of course, she wouldn't let Dean exclude her again) and Anna stop the apocalypse. Anna dies in the process, so they spare ten minutes to give her a hunter's funeral. After Cas and Balthazar and a few of their allies team up to save Sam from the cage, Jo and Sam brood over their dead girlfriends. Sam adopts a dog t. Jo and Charlie are in a committed relationship after Jo mostly gets over Anna and Charlie gets over Gilda. Dean and Cas get married, in a small church in Iowa, as it's the closest state to Dean's hometown that allows gay marriage. And then they adopt a little blonde girl they name Iris Mary. Bobby and Ellen get their happy ending in a way, getting married in a courthouse while wearing plaid and motorcycle boots. They're a perfect balance of gentle and rough, and they balance each other out. Plus, it's nice to have Ellen around- she's a good cook. Ellen dies on a hunt two days before their fifth anniversary and Bobby follows her a year later. Kevin's mom dies peacefully in her sleep. Dean never takes on the mark of Cain, but Abaddon still dies. Team Free Will and Co. go back to hunting wendigoes and shapeshifters, going after demons only occasionally, when duty calls. Dean even gets a normal part-time job fixing cars. Balthazar visits from time to time. Charlie reads Iris "The Hobbit" as a bedtime story, and both her dads take care to tuck her in every night.
One night, they're eating dinner together when Sam randomly starts crying tears of joy. "I guess hunters can be happy after all," he says. "No chick-flick moments," Dean mutters. "We all know you're sentimental at heart, Winchester," Jo snarks.
They end up having a massive group hug, then watching Game of Thrones (after Iris is asleep of course) and complaining about Joffrey.
They're an unconventional happy little family; Cas, Dean, Iris Mary, Charlie, Jo, Sam, Kevin, and Dog. Sure, they tease and bitch and lie and cheat, but they've finally found a sort of peace.They endured pain, sacrifice, death, and sadness but they made it. They earned their own happy ending.