Methods and systems for providing rich semantic feedback to programmers by executing programs, or parts of programs, in data contexts relevant to the programmer are provided. According to one embodiment, a method is provided for communicating semantic information to a programmer. A conversational programming agent of a programming environment receives (i) information regarding multiple programming building blocks and (ii) information indicative of a current situation relating to the programming building blocks. The conversational programming agent evaluates the programming building blocks based on the current situation. Then, the conversational programming agent provides semantic feedback regarding the programming building blocks to the programmer based on results of the evaluation.