The present disclosure relates to a computer implemented system and method for automatically generating messages. A repository (102) stores information related to chat sessions corresponding to a set of recipients, the information including contents of chats, historical timestamp information, personal information corresponding to each of the recipients, and relationship details of each recipient with a user;. A parser (104) parses information to generate parsed data including verbs, nouns and common phrases. An analyzer (106) analyzes the stored information to extract behavioral data of the user. A searching module (108) searches and extracts relevant data from the web based on the parsed data. A message generator (110) generates messages corresponding to each recipient.