maintaining a list of likely recipients based on the frequency the likely recipients have been messaged by a user, wherein:

(1) the list comprises the number of times each listed likely recipient has been messaged,

(2) the list contains a maximum number of recipients, and

(3) new recipients and older recipients are added to and deleted from the list, respectively, on a first in first out (FIBO) basis;

receiving an indication that a messaging system requires a recipient designation;

automatically displaying the list of likely recipients for the e-mail message, wherein the likely recipients are included in an address book associated with the messaging system;

prompting a user to add contact information of a non-address book recipient to the address book when the user previously addresses and sends e-mail messages to the non-address recipient two or more times, wherein the non-address book recipient is a second recipient designation that has not been included in the address book;

providing the ability to select one or more recipients from said list of likely recipients;

accepting a selected one or more recipient as targets for the e-mail message

determining that six or more recipients were targeted for the message; and

because six or more recipients were targeted for the message, refusing to adjust the indications in the list of frequently messaged recipients.