From the description of your convo, it really sounds like you should subtly ask him to repeat back what he thinks you are trying to say. Nicely and humbly say "um, can you do me a huge favor and tell me what you think I'm saying...I want to make sure that I'm communicating my thoughts to you correctly". This has helped us a bunch. Just my 2 cents of the day.
Anywhere is walking distance if you have the time
-Steven Wright
