Just over a year ago I decided I wanted to try cigars. I knew nothing about it and unfortunately I didn't do any forum research ahead of time (stupid I know, when there is a wealth of information out there). I did a few internet searches for retailers and went with what seemed to be a prominent one: Thompson (scream of anguish). I browsed through the site and ended up grabbing a 7 stick sampler and a Wolf v-cutter.

Let me stop for a moment and give some reflection. This was the only time I have ever ordered from Thompson and I hit the trifecta of annoyances everyone complains about from them. They called and harassed me trying to get me to join their stupid club. The sticks they sent were WAY dried out. They substituted a couple of house brands for two of the name brands in the sampler. There is a reason these guys have a bad rap on forums, unfortunately I didn't do research ahead of time.

Back to the story. I got the cigars and laid them out on the table and just admired them for a while. I decided which one would be my first smoke. After much deliberation I settled on a Gurkha Legend (mistake #2). I grabbed the cigar, the cutter, a glass of water, and a glass of Glenlivet 15 (my only good decision that day) and went out back onto the patio. I cut the cigar and then went back inside and did an internet search on how to light a cigar. Hmm, I neglected to buy a torch lighter when I made my purchase. So I grabbed the only thing I had, a BBQ lighter (mistake #3). So I went back outside and discovered that it's really hard to light a cigar with a soft flame lighter in a moderate breeze. I had to stand against the side of the house and huddle next to the wall while I tried to do it. I also discovered that lighting a cigar without inhaling is a skill that takes a little practice to achieve. After a coughing fit that lasted what seemed like 6 days I was ready to try to taste the cigar.

It was awful. Really, really awful. I did not enjoy that experience one single bit. The only flavor I got out of the cigar was ash. Looking back, there were a few reasons for this: Thompson managed to dry the thing out more than any cigar I've seen since, I scorched the hell out of the tobacco while lighting, and Gurkha failed to make a good cigar with the Legend (in my opinion). I tried another Legend (from another retailer) 6 months after the first one and still found it to be a seriously sub-par cigar.

Luckily for me a week after that first experience I had my second cigar (RYJ Bully, not from that Thompson sampler) in an experience I look back extremely fondly on and that is what shaped my future of cigar smoking. Had I not had that second experience I probably would not be smoking cigars today. On reflection, my first cigar makes for a good story and it's funny in hindsight, but it didn't do much to help me along.
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Wow that sounds like a horrible experience. Good thing you rebounded though. Just like my father used to tell me, "Try everything twice. The first time you might not be doing it right."
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Mine was an Oliva V Double Toro that I chose because the V series was on a list of highly rated cigars from Cigar Aficionado that I had brought into the humidor with me. I probably looked like an idiot. The next morning I managed to not mangle the cap with my cheap cutter and lit the thing in a breeze with a half a box of matches. Having never smoked anything before it was a touch strong, but I enjoyed the 3/4ths of it that I smoked.
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Don Diego, can't remember if it was a play boy, or a players club, but if memory serves me it was a good smoke. Felt light headed afterwards. That was the very first tobacco product I ever tried.
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Something machine made....1967 Vietnam. Also chewed on quite a number while walking point, gave me something to think about aside from the obivious.
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I have one in my humidor. It's been sitting in there for almost a year now. I still need to smoke it.
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First cigar? LOL, probably a black and mild. Then backwoods sweet aromatic. Then I discovered real cigars. :P
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Backwoods are my go to camping cigar. :-)
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I'll admit it, when it's nice out, Backwoods are my at work smoke. :-)
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Was in Iraq 2008-2009. Towards the end of our deployment my buddy and I had a "room" (more of a container) together and we'd sit outside playing cards at night. He mentioned another guy in our platoon had a humidor so we bought a couple cigars off him. The only name I can recall was Macanudo. They were super dry though, and started cracking. Spent a lot of time spitting out wrapper. Then again, we did also cut them with pocket knives lol

My first actual cigar upon getting into the hobby recently was an LHC, and I didn't care for it. Too strong for my newbie tastes I guess.
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