During my childhood and into my late teens, my paternal grandfather smoked pipes and occasionally cigars, as did various relatives and close family friends. I especially loved the aroma of pipe smoke, and as I connected it with my wonderful grandpa, I envisioned myself becoming a pipe smoker at the first opportunity. ;-) My dad dabbled in pipes and cigars now and then, and so did some of his work pals, all his age and younger. I guess that might be another reason that I wanted to get an early start - pipes and cigars just seemed like a thing that cool guys enjoyed while hanging out, watching sports, etc.
I sampled machine-made cigars like Tiparillos, White Owls, and Muriel Air Tips in my mid-teens, figuring they'd be easier for me to get and easier to get the hang of. A couple of my friends liked them, but they didn't really deliver what I thought they would. I thought maybe a pipe would be more enjoyable, so I nabbed one of my dad's pipes and gave it a try. I liked it more than I liked the Tiparillos and the Muriels, but the pipe still tasted different from what I expected. I just thought the smoke would taste the way my grandpa's pipe smelled to me.
It took a little while, but I got better at packing the pipe and keeping it lit, so I got used to the flavor and started liking it. Decided I'd better stop borrowing my dad's pipe and got a brand-new Dr. G for myself, which made a huge difference. I hadn't realized my dad's gunky old pipe was affecting the smoke, so my new Dr. G smoked about 100% better. Loved my private pipe smoking sessions through high school. Borkum Riff and Amphora became my fave mass-market blends. Meanwhile, my grandpa had started smoking Sir Walter Raleigh Aromatic and Amphora - MUCH nicer blends, I thought!
Right before I started college (and right after turning 18), I worked up the nerve to buy myself another pipe at a real tobacco shop. I was pretty shy about it, thinking I might get flak or a raised eyebrow because of my age. I was way too excited about buying a new pipe to let my shyness stop me, and I relaxed after noticing that the guy behind the counter was in his early 20s and was smoking an amazingly nice-smelling blend. When he asked me if I smoked a pipe or cigars, I said a pipe, and he started showing me pipes in my price range. I bought a no-name straight billiard with a light, smooth finish, which I still own and smoke now and then. Then I got to choose a pouch of any house blend for free to go along with my pipe purchase, so naturally I wanted what the shop guy was smoking. No surprise that it turned out to be Lane 1Q. Next thing I knew, I was getting a refresher lesson on packing and breaking in my new pipe. After firing up that first bowl, I remember thinking, "Wow, THIS is why I want to smoke a pipe!"