Abstract: A system for predictive electronic mail addressing is provided. The system comprises a computer system and an application, that when executed on the computer system, observes the instantiation of a draft electronic mail message on a client device. The system also analyzes at least one of an entry of a first addressee, an entry of text in the subject line, and an entry of text in the body of the draft electronic mail message. The system also identifies at least one list comprising a plurality of proposed addressees based on the analyzed entries. The system also displays the at least one list in a selection pane on the client device and enters the list into the addressee entry space of the draft electronic mail message when selected.