Though this would be a great post to be my 100th...
1) What is your dream (it'll never happen, but it is nice to dream) situation for enjoying a cigar? (place, people, drink, whatever it may be that makes it your favorite)
After defeating hordes and hordes of impure daemons in the name of the Emperor Of Mankind, I sit atop their purified (i.e. dead) bodies and light up the greatest cigar I can find, harvested on Holy Terra itself from the paradise Island of Kooba. Now, being a Grey Knight Justicar, merely using a match is not enough, so, I call my battle-brother Timerius over to light me up with his Heavy Flamer. Ah, the glory of Humanity and the Emperor.
...
Hey, you said dream situation You never said it had a geek limit.
2) What is your dream situation (it happens occasionally, just waiting for the next time) for enjoying a cigar? (place, people, drink, whatever it may be that makes it your favorite)
Cool day, around 4 pm, I have an enthralling book with me, a LARGE glass of ice tea, and a cigar I've been looking forward to for a while, most likely Oliva, lol. And now, the entire evening all to myself, a good smoke and the turning of pages.
3) What is your favorite place to enjoy a smoke?
Usually on my porch.
4) What is your favorite thing to be doing while enjoying a good cigar?
Read. I'm boring, I know.
5) What is your usual pastime while enjoying a cigar?
Ummm.... read?
6) What is your usual place to enjoy a smoke?
Uhhh... PORCH?!?!
7) Name 3 people (living) w/whom you'd like to enjoy a cigar?
a) Ron Perlman (actor)
b) My friend Tim (he's asthmatic, so he can't

)
c) Leonardo DiCaprio. I like him. So sue me.
8) Name 5 people from CA w/whom you'd like to herf.
A, B, C, D, and E) I have no idea. at all.
9) Name 3 people (no longer living) w/whom you'd like to enjoy a smoke.
a) David Carradine (I know he probably never smoked cigars, but this is my fantasy dammit!)
b) Mark Twain
c) my grandfather Rupert whom I never met.
10) If we could get all of CA together for a herf, what would be your idea of a great herf (site, activities, drinks, cigars, etc... be as descriptive as you can)?
Glasgow, Scotland in a forest, making our own temporary stogie-smoking territory! Food, drinks, campfires, hikes, music, the works! All in one of the loveliest places on earth.
Man... I sound like a hippie. I'm not, I promise! I just look like one and occasionally have hippie-esque thoughts!