probably should have lurked a little while longer before I grew a pair and began to comment, is it just hit or miss, how does one start an actual conversation

Started commenting about a week or two ago. It's cool. I have no complaints. I guess I'm just not positive how this works. Do i continue posting comments till people get to know my handle, do the comments just sit out there and if it's funny or insightful enough it might catch fire with the upvotes... what am I missing. Am I doing this wrong? thanks in advance.