Having (or, well, not having) awkward conversations is a matter of skill. If you've never had an awkward conversation, or haven't reflected on the ones you have

Having (or, well, not having) awkward conversations is a matter of skill. If you've never had an awkward conversation, or haven't reflected on the ones you have had, you won't realize what makes a conversation awkward and won't know not to do that. In this case the author could have answered the assumed questions rather than the asked questions, and I imagine the conversation would have gone rather differently. Unless of course he finds having awkward conversations to be amusing.