Abstract: A system and method is provided for adding an advertisement to a digital message and providing additional communication data to a recipient that interacts with the advertisement regardless of the network device the recipient is utilizing. An advertisement generator residing on a network host accepts digital messages from contributors and allows the contributors to select an advertisement to be displayed with their contributed messages. These digital messages may be sent to specified recipients or published on a Web site. Using stored personal data associated with the contributor and with the recipient of a digital message, in addition to the content of the message itself, the advertisement generator suggests advertisements to be included with the digital messages based on their contextual relevance. In exchange for including an advertisement with a digital message, a contributor is compensated.