Not sure what my first real CC was but I smoked a fauxhiba in Mexico once, right out of college in my early 20's, long before I ever really got into cigars. Yes I enjoyed it at the time, no I wouldn't do it again lol
A co-worker and I had dinner with the president of DeWalt during a trade show in Germany and he bought cigars for us afterwards. Prior to that I had only smoked backwoods, swishers and “it’s a boy / it’s a girl” cigars so it was the first time I realized how awesome a cigar could be.
Someone gifted me a Hoyo San Juan in a NHIE package. (I know who he is, he’s not on here anymore.) I was thrilled to no end, and built up my expectations beyond what was reasonable. I smoked it with a good friend and my uncle after a bbq at my house. As I recall, my judgment was “meh”.
I stuck with habanos, and I’m glad I did. Still haven’t really had a Hoyo that hits me right, and to this day, I’ve never owned more than a 5er of any HdM.