I generally have an idea of what I'm going to smoke although I may not know the brand yet. If I've had a good meal I always go for something a little more full but if it's just sitting out at a bar or golfing it's something lighter.

I normally stick to buying cigars in the robusto size. These are generally a 45 minute smoke or so and that's normally perfect for me. I do have a few larger smokes in my humidor now but they will be sitting there for a while until a special occasion when I feel like being a chimney for more than an hour.