An embodiment for creating a dialog based on anticipated questions for database driven conversations is provided. The embodiment may include receiving content from a database. The embodiment may also include identifying one or more schemas, one or more entities, and relational data in the content. The embodiment may further include identifying a semantic type and a number of distinct entries for each entity. The embodiment may also include presenting choices for one or more query targets and one or more filtering conditions to a user. The embodiment may further include prompting the user for one or more annotations and one or more clarifying questions for each chosen query target and filtering condition. The embodiment may also include generating a plurality of modular phrases and combining the plurality of modular phrases into one or more sentences and paraphrases of the one or more sentences.