Methods and apparatus for allowing parties, e.g., individuals, at different locations to participate in an on-demand content delivery session are described. Dynamically updateable playlists are used to control content delivery to the session participants in a synchronized manner. Content may be delivered to different session participants from different servers with a different playlist corresponding to each session participant being used to control content delivery to the session participant's host platform, e.g., set top box. Either party may update the playlist with, optionally, each of the content delivery servers being controlled by a different or local copy of the jointly updateable play list. Thus, an inviting party and one or more joining parties are able to participate together in an on-demand session. While the participants may be served by the same or different content delivery servers, the parties are able to share images, audio, and/or video in a synchronized manner.