A system and method are disclosed for providing interactive computer managed media bartering. Information representing criteria permitting use of personal information and/or media within advertising is received from a first user. Targeted advertising placement requests including criteria for targeting users and criteria related to requests to barter for advertising. A value representing respective advertising that may be paid with products, goods and/or services is determined based on a demonstrated interest of a plurality of users in the advertiser. Information from the first user and criteria from advertisers are processed to determine contextual elements to incorporate within advertisements. A numerical value representing an incentive for a targeted user to receive and/or be included within the contextual information is determined. The numerical value is applicable toward a redemption option. Advertisements with the contextual elements are generated and transmitted to an advertisement receiving user. The redemption option is provided to the targeted user.