The dating landscape used to be generally regulated by a traditional-normative symbolic structure which organized society towards a more-or-less clear value-form: marriage/pair-bonding.  The modern dating landscape has largely lost this symbolic structure, and consequently, it has become extremely complex and confusing: a disorienting digital marketplace of wild drives and images disconnected from long-term value-forms.  Javier Rivera and I attempt to philosophize about this complexity and confusion with a psychoanalytic perspective.  We discuss the possibility that an internal-intersubjective symbolic structure can be re-organized if we consciously accommodate the real as an impossibility.