"Backwoods Hick" as a second language

Maybe I'm just getting old, and maybe I'm just not wording my questions clearly, but more and more it seems like when I ask a question, I get an answer that is not related to my inquiry.

Here's an honest to goodness conversation.  Please be frank with me and tell me if I was not communicating clearly.

Me:  Excuse me, we're not from around here.  Is this The White Bar?
He:  The White Bar?  You mean McGinney's?
Me:  Is that what this bar is called?  We were told to go to The White Bar.  Do you know where that is?
He:  Are you looking for the 25th anniversary?
Me:  The.  White.  Bar.
He:  This is where the McGinney's party is.

The guy was sincerely nice and completely sober.
It's like, "You're here.  Certainly you must be looking for this party."
I think I could have been asking where the gas station was, and he'd have given me the same answers.

***

Here's another one I had while instant messaging computer support at work:

Me:  I know you guys have a big update coming later this week, but it appears I'm using a version that is two updates behind.  When you guys have updates, do we get them automatically, or do we need to do something on our end?
He:  Updates to the cloud are.  Each are to www.ourwebsite.com/update .
Me:   What does that mean?
He:  Updates to the cloud are automatic.  Each to www.ourwebsite.com/update.
Me:  So I have to go to that website to get updates?
He:  Yes.
Me:  So, that's why I'm two updates behind?
He:  I don't understand.
Me:  I've never been to that website.  I'm two updates behind.  So, to get updates, I have to go get them, right?
He:  I'm going to have a tech contact you to explain how it works.
Me:  The only question I have is... When the update comes this week, do we have to do something to get it, or do we open up the program one day and, boom, it's there?
He:  I don't think I'm communicating clearly on chat.  I'm going to have someone call you.

Dude, the original question had an A) or B) answer.  You gave me answer 3).
This? or That? 
The answer is tree!
What do you mean by "tree"?
The big tree.
You're killing me, Smalls.