Infuriating conversation, bluntness, role reversal and regret

Oh sonya your man problems truly abound. If you're not interested, don't act interested. If you are, don't act sarcastic. It sounds like you want to be chased but don't know to what end.
ITA. I am not even sure what the point of your post is. You start out by saying he's basically a dullard...so why are you wasting your time---AND his---by stringing him along? I don't get it.
 
So do you plan on spending time with this guy solely as friends? Or is there a possibility of just having a casual romance? I think you made it clear to him that a "relationship" is not a possibility so I'm not sure why you might hang out with him in the future. That might just confuse him even further. I think with women even the most intelligent guy can be confused by small things so I always found it best to be clear with my words and for my actions to follow accordingly.
 
So I met a guy who is the most awkward conversationalist I've ever met. It takes 40 minutes for him to get the point. He skirts the issue by talking about repetitive things that aren't very interesting. Worse of all, he stops in between every word. It's quite frustrating talking to him on the phone!

To talk just about the quote - -

I have a dear friend who also is Conversationally Challenged.

He doesn't going into detail. He goes into MINUTIAE!

My mother is the same way. Both drive me up the wall pretty quickly, especially my mother. She works in the medical field and loves to tell me details of people's health problems. :sick:

I have learned some coping tricks.
Mainly I don't give them my full attention. I have something else I am doing.
While we sit talking, I open mail, sew, fold laundry, whatever.
When I talk with my mother on the phone, I have the TV turned on with the sound turned off.
I always offer to drive if we are going anywhere.

Both friend and mother think I just can't sit still. ;)