Disclosed are systems and methods for initiating communication between users of a user group based on machine learning techniques. The disclosed systems and methods provide a novel framework for automating communication scheduling and communication initiation based on user communication objectives and machine learning techniques. The disclosed framework operates by leveraging available user provided communication parameters, user provided objectives, and various real-time data associated with the users, and using the aforementioned data as inputs for machine learning models, in order to schedule communication between the users, automatically initiate communication between the users, or transmit communication notifications to the users.