Aspects of the present disclosure relate generally to reminder systems and, more particularly, to a contextual item discovery and pattern inculcated reminder mechanism and methods of use. A computer-implemented method includes: determining, by a computing device, an event in which a user will participate; associating, by the computing device, one or more items with the event; determining a location of the one or more items associated with the event including that the user does not possess any combination of the one or more items; and providing an alert to the user that the any of the one or more items associated with the event is not in the possession of the user.