Natural language processing is a difficult problem and is currently a technical barrier in building personal assistant agents that aim to interact with humans in natural language. One possible solution is to rely on humans to restrict or adapt their language into more computer friendly ways. We study the feasibility of this approach in the context of a personal assistant agent that parses emails relevant to meeting scheduling in order to assist the user in calendar management tasks. We design an experiment in which humans are given email writing tasks and then given feedback on how well those emails were understood by an agent. We wish to see if the humans learn to adapt their email writing to what is understandable by their agent.