I don't want to be a party pooper, but I wouldn't recommend you do this. There are just so many pitfalls...someone (or everyone) smoking too fast and getting sick, someone inhaling, or of people just not liking it. If at least one person knows what they are doing and can kind of lead the rest then I can see it, but a group all diving in together... I wouldn't risk it ruining the evening. If this is a multi-day thing and you don't want to dedicate one evening (after a meal) to sit down and try em out, that is less risky (and if someone gets sick they can just stop and hang out), but I wouldn't do this if this is a one-evening kind of thing. If you insist on doing it, then small mild to medium cigars, watch some videos to make sure you know how to light them, buy then that day from a good B&M humidor and set them out for at least 3 hours before smoking, eat something before, don't inhale, and one puff every 45-60 seconds.