I've found that too - some men I can converse with easily, while others it's more of a slog.

Maybe for the women who say, "what is this, an interview?" they feel like you're asking too many questions in a row. Maybe ask a question and then wait until they ask one.

And as far as "you're the man, you're supposed to know."

Maybe you're just asking them for their preferences too much. At some point, both people just have to be themselves and see if they mesh, naturally, instead of just trying to do the thing that pleases the other person.