A computer implemented system and method for encouraging frequent and purposeful electronic communications from caregivers to individuals with impaired memory to, inter alia, alleviate feelings of isolation and improve memory. The system includes a Web-based application through which caregivers send text, image, voice and other forms of data for receipt by the sufferer on a PDA having a simple user interface. The Web application records the dates and nature (i.e., text, audio, photograph, video) of communications sent by each caregiver, processes the data in order to display it in a variety of meaningful ways to all caregivers, thus creating a peer-pressure environment to encourage more frequent communication. The Web application can also be programmed to send electronic reminders to all caregivers who opt-in to the service requesting that they send a communication to the sufferer, and more particularly to individual caregivers whose frequency of communication has been inadequate relative to a group of caregivers or to predefined expectations.