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The Roadhouse is more or less empty when they show up- that is, until Dean feels the gun on his back. “Oh God, please let that be a rifle,” he says.
“No,” comes the voice. “I’m just real happy to see you. Don’t move.”
He tries to grab the gun, gets socked in the face, and then Sam walks in with a gun to his back. When the woman holding the gun hears him speak, her expression changes.
“Sam?” (and then she hesitates, just for a few seconds, and Dean knows what she’s thinking, and wishes she wasn’t) “...Dean? Winchester?”
“Yeah,” Dean says at the same time Sam does.
“Son of a bitch,” she says.
The girl who punched Dean says, “Mom, you know these guys?” and the woman says,
“Yeah, I think these are John Winchester’s...boys.” Dean winces at the hesitation. The woman lowers her gun with a laugh. “Hey, I’m Ellen. This is my daughter, Jo.”
Something clicks in Dean’s mind. One of the only times John had ever mentioned the Harvelles-
Jo interrupts his train of thought. “I thought John Winchester had a daughter.”
Sam looks like he’s ready to correct her, or perhaps say something angry, but Dean beats him to it. “Well, you thought wrong.” He thinks: I thought Ellen Harvelle had a son. He doesn’t say anything, though, especially considering that he’s probably wrong.
He gets along with Jo surprisingly well, all things considered. Finds out her dad died when she was a kid. There’s something to relate to, he guesses. He almost hits on her, and then feels bad about it: again, considering the circumstances, wrong place, wrong time.
Ellen offers them a place to stay, and he considers saying yes, but he turns it down. Still, he thinks. He trusts them. For whatever reason, he trusts them.
The more he talks to Jo, the more he’s glad he decided against hitting on her that first day. The best way to describe her, he decides, is a kindred spirit, specifically like in Anne of Green Gables (a book he’s read, but would never admit to enjoying). Jo understands him, and he likes to think that he understands her.
The way she talks, though: it’s strangely guarded at times, in a way that makes him wonder if-
"I don’t know,” she says. “Like, when I think about my dad, I think, what would he say if he could see me now? And, you know, my mom says he’d be proud. But I don’t wanna just take her word for it.” She hesitates. “I just- I know I’m not what he would’ve expected, you know?”
“I get it,” Dean says, thinking of Mary.
“Do you?” Jo says bitterly. “Don’t answer that, I’m sure you do. Sorry, I just. Yeah.”
“Sometimes when I think of my mom, it feels like I betrayed her.” He doesn’t say why. He’s sure Jo can guess. I thought John Winchester had a daughter. She hasn’t mentioned it since, and he isn’t quite sure whether she knows or not.
Maybe it doesn’t matter.
Ellen is- well, a bit overprotective of Jo. “I mean, I can handle it!” she says indignantly one day, sitting next to him on the steps of the Roadhouse. “I mean, she treats me like a baby. It’s ridiculous.”
“Yeah,” Dean says. “Too bad, huh.” Privately, he’s jealous, but he would never admit that. He imagines how his life might have gone if Mary was still alive. The idea of having someone to protect him has its appeal. And now that John is dead- well. It’s not like he ever did much protecting anyway. But, Dean thinks, he did his best. Out loud, he says, “Don’t tell Sam I said this. But hunting really isn’t all it’s cracked out to be. Sometimes I wish-” He cuts himself off. There’s no point.
Jo kicks around at the dirt in front of the steps. “You can say that. But at least you get the choice, you know?”
“I don’t,” he says quietly. “I really don’t.”
He feels bad about taking Jo’s case, until she shows up, and he immediately feels. Well. He isn’t sure. Maybe overprotective. Ellen calls, and he doesn’t tell her. He’s worried, sure. And kind of pissed, but not really. And still, he feels almost a sense of excitement. He likes Jo, and working a case with people really is the ultimate bonding activity. Sort of.
Jo accuses him of thinking Dean can’t do the job. “Sweetheart, this ain’t gender studies,” he says. It’s a dick thing to say, and he knows it, but. Well, the more he thinks about it, the more he wonders if he’s more protective of Jo because she’s a girl- and, yeah, okay, that might be part of it- but she’s so young and inexperienced. And still-
Her first hunt is with him. That’s something he’s more proud of than he’s like to admit. Dragging people into the life is one thing, but if she was gonna hunt anyway…
Of course something goes wrong. Something always does. Jo gets taken, and then almost immediately after Ellen’s on the line, demanding to talk to her. “She’s gonna have to call you back,” Dean says. “She’s taking care of, uh, feminine business.” It’s a lame excuse, but it’s the first thing that pops into his head.
“When you say ‘feminine issues,’” Ellen says slowly, her voice cold, “are you talking about menstruation?”
“Uh. Yes, ma’am.”
"What a surprise,” she says flatly. “Stop lying to me, boy.”
He breaks and tells her everything. She tells him she’s heading over on the first flight she can get. Any excitement Dean felt at the beginning of the case has fizzled out into guilt, fear, and self disgust. When it’s all over, they fill the sewer with cement and sit around waiting for Ellen to show up. Jo makes her way over to where Dean sits and says,
“God, she’s gonna kill me.”
“Nah,” Dean says. “She’s angry at you, but she’ll kill me.” He turns to face her. “Your mom’s a hard lady to lie to.”
“What did you even say?”
“Told her you were having ‘feminine troubles’ so you couldn’t come to the phone. She saw right through it.”
Jo snorts. “No kidding.” She takes a deep breath. “Dean, I’m trans.”
“You- what?”
“Yeah, so unless a medical miracle happened, of course my mom wasn’t gonna believe you.”
“You- oh.” He thinks back to the conversations they’d had in the past, about what their dead parents might think if they could see them now, and it puts them in an entirely new perspective. “I, uh. Yeah. Me too.”
“Yeah, I wondered about that,” she says apologetically. “Sorry about that daughter comment the day we met.”
He shrugs. “It’s okay. Sometimes I feel like that’s still what I am.”
“Yeah,” she says quietly. “Yeah, I know what you mean.”
