Abstract: A privacy agent programmatically monitors and maintains transactional anonymity between users on an Internet web site. Each user on the web site is required to provide identifying information to establish an account on the web site. The identifying information is validated before the account is generated. Then, users are permitted to post messages on the web site to initiate and to negotiate transactions. Initial messages may be viewed on a public message board, while responses and subsequent message interactions are posted to a private area. All messages are monitored programmatically to prevent unauthorized disclosure of a an actual identity of a user. Each user is permitted to gradually reveal an actual identity to other users through private message postings.