I've only smoked with someone twice come to think of it.
First was in Iraq in 2008 (knew nothing about cigars then). On our days off mission, my buddy and I would sit on the front porch of our CHU and smoke a cigar while listening to music and playing poker. Good times. Actually kind of miss it. Our team leader had a humidor, although I don't think he knew anything about maintaining cigars because they were super dry. He would let my buddy and I just grab a cigar of our choice. I remember cutting them with our knives and spitting out tobacco the entire time
I also recall inhaling a little bit because I was a complete rookie and feeling sick to my stomach the rest of the night.
Second time recently with my little brother who doesn't smoke but begs to try a cigar every time I see him so I gave him a Punch and he enjoyed it. He's 17 so he won't be a smoke buddy any time soon haha Unfortunate because he lives with my mom and she has a nice porch for smoking!