>>Learning Java first will be even more difficult and may cause long-term damage depending on the amount of OOP koolaid he ingests.
What kind of long-term damage are you talking about? Are you saying there's anything wrong with OOP as a paradigm, or something wrong with Java w/r/t OOP? Or am I missing your point entirely?
The danger is that a person may think that the way things must be done in Java is actually a worthwhile way of doing things in general. Such a person would be in a state of permanent confusion in which the meaning of the question "How will I solve the problem?" has become "How will I partition the behaviors and data involved in a solution to the problem?" This second question is a good thing to think about, but not before the first one, and certainly not instead of the first one.
I don't think it was a dumb question. I didn't actually encounter any people like this for a long time.