It will be 20 years in June 2011. My grandpa (Who smoked cigars for 60+ years) gave me my first cigar for my high school graduation....1991. My first box was Spring 1992. Until 2005 I smoked occasionally. I became a super freak in 2005.
My uncle smoked custom rolled cigars and gave me a couple when I was in high school. My friends and I dug them and afterwards would pick up cheap cigars at the convenient store on occasion (we used to call all cigars regardless of brand "Macanudos" because that's what they had at the convenient store). During college and law school I started to get more into cigars and smoked just Fuente Hemingways and a few Ashtons and Padrons. Then after law school I discovered Cubans and never looked back. So all in all around 22 yrs.
My uncle gave me my first good cigar about 5 years ago, after my grandmother's memorial service. Until then, I occasionally smoked cigarettes socially. My girlfriend (now wife) forbade the cigarettes, but said she didn't mind cigars. I bought some decent cigars to smoke with a couple of friends the night before my wedding (Oct. 2007), and I've been smoking cigars ever since.