A system, method and graphical user interface (GUI) are described for managing a contacts and calendar database within an online stationery/card service. For example, a system implemented by an online stationery/card service allowing a user to personalize and send non-electronic stationery/cards is described, the system comprising: a graphical user interface for personalizing and sending non-electronic stationery/cards comprising: a reminder list comprised a plurality of reminder entries, each of the reminder entries identifying an upcoming event including events generated based on a specified relationship between the user and one or more contacts stored in a contacts database of the user; a recommendation region comprising a plurality of stationery/card design recommendations, the recommendation region populated with stationery/card designs associated with a specified one or the one or more entries in the reminder list, including the events generated based on the specified relationship between the user and each of the contacts; and a stationery/card personalization engine executed in response to the user selecting one of the stationery/card design recommendations from the recommendation region, the stationery personalization engine providing the end user with a set of personalization options related to the selected stationery/card design, and generating personalized stationery with the selected stationery/card design based on user input.