You might be on to something. There is something socially awkward about him. I only just met him and don't know much about the guy. But, he was giving me all kinds of advice about how you can take advantage of your credit card company, get the airlines to comp you a ticket to Asia, etc. All con artist type stuff. He was very proud to have figured out how to game the system for his advantage. Most of us would consider the advice he was giving me to be dishonest.
The times I have been around a couple of folks like that I cannot help but to egg them on by asking detailed questions concerning the flim flam they are trying to describe. It's usually at least 30 minutes before they realize that I am taunting them in their general direction ($1 to Holy Grail). I admit that I am usually way too easily entertained.