I wish I could say that I had a grandfather or father who smoked a pipe (dad smoked/smokes cigs, but that hardly counts) or some other adult figure who led me to the hobby...to be 100% honest, I started smoking the pipe as a joke.
In college, there was a group of guys who smoked cigars outside of our dorm room in the evening. This wouldn't have been a problem (cigars can be wonderful and their smokers can be fine folks), except they were the "we're in college and awesome because we smoke cigars, so we'll stand where we get the most attention just to show off our total badassery" kind of cigar smokers. So, some of us thought it would be amusing to smoke pipes and act very "proper" right next to them. A friend had a bunch of his grandfathers old pipes, we each grabbed one and had some fun with it for a week or so (typing this for an unfamiliar audience, this seems entirely pathetic...I guess you had to be there).
At any rate, even though we were making a joke about it and no idea what we were doing, it was fantastic. Really, really fantastic. And it stuck...at least the idea of it did. We had to return the pipes, and I wasn't about to run out and spend money on something as outdated as pipes and pipe tobacco - after all, what early 20-something smokes a pipe, for cryin' out loud?!?! Still, I couldn't get it out of my head.
Two years later, still in college and having developed a bit of a taste for cigars, a fellow student and cigar smoker revealed that he also enjoyed a pipe every now and again. We'd planned to have a cigar one evening, but he brought along an extra pipe just in case I'd like to give it a try, this time "for real." I did, and was hooked. The next day I was at a local tobacco shop in the Columbus area buying a pipe and three small samples of tobacco.
The rest, as they say, is history.