(For a bit of a backstory, this question is related to this one here)
I have a friend called Bob. He's part of a group of friends I meet with regularly. Bob has a very direct, yet cryptic communication style. I find this is rare because usually people who are poor at communicating are not direct. He uses a lot of idioms, expressions and sort of has a spiritual sense about him (which surprises me because he also has some very conservative opinions and has told me he is not religious).
For example, he asked to have a meeting with me. One of the first things he said is that he's frustrated with me because he doesn't know what I'm trying to give the world. I can only guess he was referring to what I'm doing with my career, but I rather not have to guess when it's a main part of a meeting that lasted several hours long. He often uses expressions like "I'm holding your feet to the fire" which I'm not fully clear what he means. He speaks in a poetic way, which I don't really like in the sense in poetry it's nice to infer a hidden meaning but when I'm talking to someone I prefer to make certain I know what they're saying.
This is stressing me out. He's an intelligent person I have a lot of respect for. How can I address the issue so I can sincerely understand him better? Another thing that messes me up is he goes on sort of monologue and I find I don't get the chance to ask questions to clarify what he means, unless I interrupt.
I have had trouble addressing this issue because 1) he speaks so long I don't have a chance to ask for clarification 2) it's almost as if since I half understand it I don't realize I should have asked for clarification until much later 3) it's my experience that people just repeat themselves in the same unclear way when asked to explain