I smoke once a month with about 10-15 guys, been doing it for years now. I'd consider three of them close personal friends, one of whom I smoke with at least 2-3 times a month depending on our schedules. My brothers-in-law come over about once a week and smoke with me, but they're more pipe smokers when on their own.
I probably have 9-10 regularly-smoking friends right now. That number has waxed and waned as friends have moved here or moved away.
I'm fortunate to have cigar smoking friends in most of my circles; my own friends, my wife's family, my church, and a few guys at work too.
Ironically, as a strong introvert, I prefer smoking alone 99% of the time.