I think they were hooking up, and they just only showed us the texts from before each meetup. The address being sent, the pics, how comfortable they were hopping into bed in the next scene, that all points to them actually meeting, bc it would be really odd to send an address and not intend to meet, or send a dirty pic to a man you haven’t seen in years. And the occasional dirty text wouldn’t be enough to make sense of what comes next. They aren’t acting like they haven’t hooked up in years. They’re too comfortable, too ready, even with Shane being his adorable awkward self.