How we listen to the potential space of online relations is rapidly becoming part of our daily work. Two treatments are examined where themes of sexual shame, repression, and relational difficulties were found and refound through online relating and hooking-up. Consideration is given to the ways in which online exploration opens a potential space that affords sexual practice and the reach of relationality. Moving with these patients into this potential space opened onto an intriguing and productive relational field. These cases help illuminate a shift in our modern social order, and how that shift has followed on a reconsideration of our psychoanalytic ideals about sexual well-being. We are now positioned to reflect not only on the evolution and revolution of our shifting sexual cultures, including the increasing role of technology in our modern relational world, but on how this new world finds its way into our consulting rooms.