Abstract: Improved techniques for targeting advertisements are provided, which take into account the content of electronic communications delivered via text messaging and/or other forms of communications. The system may automatically select advertisements based on message content, and the selected advertisements may then be displayed alongside messages, and/or embedded in or included in messages, for presentation to the sender and/or recipient of the message. Overall conversational context, including content of past messages between the parties, can be taken into account in selecting advertisements. In at least one embodiment, the content of a displayed advertisement can change dynamically in response to changes in the subject of a text conversation. Senders of messages can be rewarded for allowing advertisements to be embedded and/or displayed in connection with their messages.