Context-specific instant messaging is presented. A user views a page of data that is segmented into regions. The user performs a user action (e.g., a mouse click) and, in turn, a message generator displays context-specific phrases for the user to select based upon the region that the user action was performed and a corresponding object type. When a region corresponds to a meeting time, a context-specific phrase may also be time-sensitive. When a region corresponds to meeting participants, a context-specific phrase may include recipient identifiers. The user selects one of the context-specific phrases, and the message generator invokes a message session between the user and a recipient based upon the selected context-specific phrase. The message generator includes a link to the corresponding object such that the message recipient may easily identify the context of the message.