A random question has no Explainable relevance to the moment. A question that elicits gross mental images, slanders people or embarrasses your date is a Chinese finger trap of conversational Homicide. 

A vanilla question can feel like a Cover-Up as if you can't think of anything good to talk about so you ask where she bought her shirt. If you ask a predictable, non-creative question about something you don't really care about, people make a mental note in their minds that you are a simple-minded person with little imagination.

The key to a scintillating and kinetic conversation on a date is one’s ability to ask really good questions. But before we talk about how to ask really good questions, it’s crucial to know what really bad questions look like.