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I used to do a lot of international business. In my travels, many of the Asians, Europeans and Central and South Americans enjoyed a cigar after dinner. Although, I am not a cigar smoker, I would join in. I liked the small Cubans. The large ones were just to strong for me.
I was in Honduras and a General (military) threw a party at his house. They had some great cigars. It was very bad form not to have a cigar with him.
And yes, they go very well with red wine.
Smoking cigars struck me as a male bonding ritual and frequently used to celebrate the making of successful business.