The disclosed methods and systems allow individuals with speech challenges to convey personalized expressive content to others. Implementation is performed on widely available and popular wireless handheld multimedia devices, which may help foster acceptance of the individuals and minimize any perceived differences. Users may easily create and add personalized content to the devices and may quickly customize the content selection interfaces of the devices. These tasks may be accomplished using either the devices themselves via a device-based content authoring tool running locally on the device, or using a Web-based authoring tool on a network server. The Web-based authoring tool allows users to create, capture, and store personalized content and customized content selection interfaces on the network server from virtually any location in the world with network access. The personalized content and customized interfaces may then be downloaded and synchronized automatically on the devices from time to time or as needed.