I think we can safely assume that Josie's had been Matt and Foggy's drinking place for a long while (I like Foggy's line "this place is a shithole but it's our shithole" and how familiar he is with the other people frequenting the place).
I'd really like to see their relationship through the years seen through Josie's point of view : D it's one of my favorite tropes and this kinkmeme is full of amazing talented people, so I guess I'm gonna leave this here and hope someone likes the idea enough!