The subject invention provides a unique system and method that facilitates providing content-targeted advertising to a user based at least in part on the content of a user action. The user action can be performed in connection with an outbound messaging system, a real-time messaging system such as a chat or instant messaging, a game environment, and/or calendaring system. The system and method analyze at the least the content of an outbound message and then present a content-targeted advertisement based on the content of the message. The same can be done with respect to calendar entries. However, outbound and inbound calendar entries, invitations, and responses to invitations can be analyzed for content and have content-targeted advertisements presented to the sender or receiver of such items. User privacy can be maintained and/or increased by allowing a user to opt out of content-targeting advertisements. Reasons for being targeted can also be provided to the user.