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Here's the deal: that Winchester boy got grabbed out of hell and just because he and his brother aren't talking to many other hunters, doesn't mean the other hunters aren't talking about them. There's a lot getting said, about the boys' increasingly strange situations, about Lilith, about the breaking of the seals.
Jo was waiting tables in Barstow when the word started going around, Dean Winchester had gotten himself saved. She hadn't hunted anything in months. Truth be told, she was hiding herself and her hurt out there in the California desert. But then Ellen called for a briefing on the war at hand, the one they'd all been talking about since back when the Roadhouse was still standing. So what could she do? The only thing a hunter's kid knows how to do: get back into it.
Ellen's got her traveling the country, searching for possible seals that Lilith hasn't hit yet. The mission, her mama tells her once a day, is simple recon. you do not engage, joanna beth, you hear me? Jo doesn't argue. She checks in once a day, twice if she's closing in on something promising. She calls in any other hunter in the area if she spots demons. She doesn't engage.
She found out Dean's PO box almost by accident. She won't tell you how. She isn't sure how often he clears it out; she isn't even sure if he remembers he has it. She travels halfway across the country and she doesn't write him. Until she does.