A system, a method, and a user interface are described for personalizing and sending stationery/cards. A reminder list on the user interface includes a list of reminder entries each identifying an upcoming event including events generated based on a specified relationship between the user and one or more contacts of the user. A recommendation region is populated one or more recommended stationery/card designs associated with one of the entries in the reminder list. A stationery/card personalization engine provides the user with a set of personalization options related to the selected stationery/card design, and generates personalized stationery based on the selected stationery/card design and the user input.