Enabling a user of a video chat application to a virtual video message answering machine to contextually provide a video message to at least one other user of the video chat application for play back if the user is unavailable. The video message can be arranged to be played when another user attempts to initiate a video communication session with the unavailable user or during an existing video chat session after the user becomes unavailable. Also, the user can choose one or more contexts for playing back a video message to one or more other users that are likely to be participants in a future video communication session. The other user is provided with a user interface that enables the other user to record a video message reply for subsequent playback by the unavailable user.