I think my first serious cigar was at a golf tournament in the summer of ‘95. The vendor provided cigars for all the participants. The other 3 people in my foursome did not want their cigars, so I smoked all four during the round (18 holes).
That happened a few more times and it was downhill from there
In 2000 my wife and I along with our youngest son went on a golfing vacation to Vero Beach. We flew in to Orlando and went to Disney World for a day. While we were at Downtown Disney she saw the cigar store (Sosa) and knowing that I liked cigars while golfing, she suggested that I pick up a few cigars. She probably regrets that now, but that was the beginning of my serious slide down the slope.
After that vacation I got home and bought a humidor and started hanging out at the local cigar lounge. A few years later I met markem and several others from CS/CA. And the rest is history