Any time we write or speak, we have a goal in mind: to communicate an idea from one person to another. What that idea is varies, but consistently, how we form speech is used to optimize the expression of this idea. For instance, if you took a trip to New York yesterday, but your friend asked "Did you go to Philadelphia yesterday?", you might respond "I didn't go to PHILADELPHIA yesterday," emphasizing where you went, but not denying that you went somewhere yesterday. This is because the critical information here is the location, and not anything else in the sentence– that information is then in the background. So your friend may then ask "Then where did you go yesterday?" To collect more data on this phenomenon, I conducted an online experiment where participants were shown statements like the one above– some with emphasis and some without– and rated the naturalness of questions like "Then where did you go yesterday?" On average, the questions were rated as more natural when what was being asked about was emphasized in the previous sentence. This suggests a strong relationship between the status of information in a conversation (as either new vs old, critical vs backgrounded) and how natural sentences are formed in conversation, thus revealing just a little bit more about how language transforms from our thoughts to real-life speech.