A system and method of managing user engagement with a musical playlist provides feedback for a host and allows attendees to directly engage with the host to adjust a playlist for an event or social gathering. The system includes at least one remote server, a corresponding user personal computing (PC) device, and a corresponding host PC device. The method begins by prompting the at least one host account to initiate an event session for a plurality of attendee accounts and then to designate a plurality of playlist songs with the corresponding host PC device. The event session is managed in between the host account and the plurality of attendee accounts through the remote server. A current song is played during the event session and feedback is relayed for the current song with the corresponding user PC device. The feedback is then outputted with the corresponding host PC device.