A system and method allowing a session initiator to select from among multiple privacy levels to be applied to an instant messaging session. When a user initiates an instant messaging session, multiple selectable privacy settings are presented, from which the user can select. The disclosed system may provide a session initiator with a user interface that enables selection from among privacy settings that prevent the session contents from being copied and pasted while the session is in progress, prevent any saving of the session contents by any user, prevent the session contents from being forwarded via electronic mail, prevent display of previously viewed session contents while the session is in progress, and/or prevent screen shots from being made of the session contents while the session is in progress. Flags representing one or more of the multiple privacy settings may be stored in association with an ongoing session, and/or in association with the stored contents of a previous session. In one embodiment, only the session initiator can select from among the multiple privacy settings, and may be provided with indication in the user interface of the privacy settings that are supported by individuals listed in their buddy list.