Lateral Thinking Game

This is a puzzle solving game of sorts. One person posts a puzzle and the others are supposed to solve it. To do that, they are required to ask simple (or not so simple) yes/no questions. Based on the answers to these questions, they have to figure out what the first person wants to hear. A classic example, spoilered for the sake of convenience:

Spoiler

A man walks into a bar, and asks the bartender for a drink of water. The bartender pulls out a gun, points it at the man, and cocks it. The man says "Thank you" and leaves. What happened?

The question and answer segment might go something like this.
Question: Could the bartender hear him? Answer: Yes
Question: Was the bartender angry for some reason? A: No
Question: Was the gun a water pistol? A: No
Question: Did they know each other from before? A: No (or: "irrelevant" since either way it does not affect the outcome)
Question: Was the man's "Thank you" sarcastic? A: No (or with a small hint: "No, he was genuinely grateful for some reason")
Question: Did the man ask for water in an offensive way? A: No
Question: Did the man ask for water in some strange way? A: Yes

Eventually the questions lead up to the conclusion that the man had the hiccups, and that his reason for requesting a drink of water was not to quench his thirst but to cure his hiccups. The bartender realized this and chose instead to cure the hiccups by frightening the man with the gun. Once the man realized that his hiccups were gone, he no longer needed a drink of water, gratefully thanked the bartender, and left.

And feel free to ask more than one question in one post. Alright, let's start with an easy one:

Who is that man in the orange suit?

 

Is it a spandex suit?

 

Is it a spandex suit? No

 

Does the man have a briefcase?

 

Does the man have a briefcase? No

 

Side-ways Thinking Game

Is he in jail, a prisoner, or anything of the sort?

 

Is the suit important?

Also.

Are you and I the only ones who will ever post?

 

Is he in jail, a prisoner, or anything of the sort? No
Is the suit important? Depending on your definition of "important", but more yes than no
Are you and I the only ones who will ever post? As you see, no

 

Does the suit define the man?

(As in, is he required to wear it to be identifyable.)

Also, are you aware the question was directed at Lowell, 'cause its your thread so you don't count.

 

Does the man in the suit have special abilities?

 

Does the suit define the man? Yope
Also, are you aware the question was directed at Lowell, 'cause its your thread so you don't count. Well, I am now
Does the man in the suit have special abilities? No

("Yope" is a portmanteau of "yep" and "nope" and it means an answer that would be "Yes, but..." and "No, but..." simultaneously.)

 

Is this man addicted to any form of a drug?

 

Is this man addicted to any form of a drug? Irrelevant/Unknown

 

Does the man in the suit have impaired vision?

 

Does the man in the suit have impaired vision? Yes

 

Does the man have a tie?

 

Does the man have a tie? No

 

Does the man ever wear a tie?

 

Does the man ever wear a tie? Unknown, probably yes

 

Does this man have a job?