System and methods are disclosed that replace shorthand items such acronyms, abbreviations, jargon, slang, codes, shortcut expressions, emojis, stickers, ideograms and emoticons in an electronic message with expansions, which are definitions or meanings of the shorthand items. Based on a number of times previous messages to the recipient included an expansion of the shorthand item, the system determines whether to stop or to continue expanding the shorthand item in electronic messages to that recipient. This may be based on a threshold or other preferences selected by a user. The system also indicates which text in the message presented to the recipient is an expansion of a shorthand item and suggests shorthand items to insert into outgoing messages based on the text of the message.