A system and a method are disclosed for dynamically generating a contextually desirable message ready for a user to send out to other participants of a scheduled event. A user context is determined for a scheduled calendar event and then logic rules applicable to the user context are identified and used to identify contextually desirable messages. Options for dynamically generating the contextually desirable messages are provided to the user along with information about the scheduled event. Upon a user selection of one of the options, the corresponding contextually desirable message is generated and its content is pre-populated according to the applicable logic rule.