I started pipe and cigar smoking when I was around 19-20. I preferred the taste and length of smoke to cigarettes.
I never smoked regularly. I started smoking cigars about 7-8 years ago at different settings: fishing, camping, gambling, golfing.
Lately,in the last five years, since I was 36 or so, I started liking cigars regularly. Thats when I started building a collection and improving my taste in better cigars.
I think it has been an older guy thing since the 40's or 50's. Smoking a cigar takes time and planning. Not a lot of younger people have the time or patience to sit back and have a smoke that takes a better part of an hour. (Or, in the case of a Hemingway, a day).
If you are a younger person with the luxury of time to relax, then you are truly lucky. I rarely did, I don't really now but I make time and places to have a cigar.
Honestly, smoking cigars is something that you have to give and take. Many places are closed to smoking, many scenarios aren't conducive to lighting up a cigar: (like work places, some social events, while playing many sports, visiting other people's homes, kids events etc.).
Having a good long cigar takes time and planning if you don't want to put it out. I guess time used to be the older person's domain.