Systems and methods for reminding a user or a group of users about one or more items related to an upcoming event. The upcoming event is identified based on user data and a context for determining a list of items useful for the upcoming event is obtained. The list of items for the identified upcoming event is determined, using the context, and item reminder enhancement factors are determined in response to the upcoming event and the determined list of items. Content selection models are determined based on the context, the user data, and the item reminder enhancement factors. Conversational content for engaging the user or group of users is generated by applying the content selection models to a plurality of potential content. A conversation trigger signal is determined, and the conversational content is presented to the user via a computing device in response to receiving the conversation trigger signal.