I should clarify that I very much enjoy the occasional cigar: sometimes at a lounge with a friend, sometimes on the back patio with the ball game on the radio (or even just the birds in the trees), or very occasionally up in the listening room with a most excellent LP, and always accompanied by an appropriate beverage.
I don't think living a healthy lifestyle necessarily precludes an occasional indulgence, and a fine cigar is pretty high on my list of enjoyable pleasures and for which I think there is little, if any, dire consequence - it's all about moderation. I may go months without giving my humidor a second thought, and other times I may visit it two or three times a week. (I have similar relationships with the liquor cabinet and wine cellar.)
It's considered appropriate to not directly inhale cigar smoke as you commonly would cigarette smoke, so a proper cigar experience should never leave you coughing up a lung. I have a couple of friends who are pretty serious cigar consumers during the summer months, as they choose to smoke only outside. Once the weather turns cold, they don't light up again until spring and they suffer no undue withdrawals. Again, it's all about moderation. And I'm certainly not trying to paint the picture that cigars are the pinnacle of nutrition, but I don't think they're quite as bad as they're stereotypically made out to be, "dog-rockets" notwithstanding.
I should also add that I'm in my mid-late 30s and have never smoked cigarettes, though my parents were moderate smokers when I was a kid. And I only came to enjoy cigars several years ago, mostly after developing tastes for brandy and Scotch (not so much on Port) and reading much rhetoric about those classic cigar pairings - I actually read three books about cigars before I ever even tried one!