First abortive attempt at around 24 years old (almost 20 years ago now) with my dad's old Grabow Duke and Borkum Riff. His pipe smoking was a very brief phase around the time he gave up cigarettes. That pipe had sat around in a drawer for years when I picked it up. I put it back down for all the reasons newbie pipe smokers quit, tongue bite, sour pipe, gurgle, etc.
Fast-forward to 2012 and I became interested again with a rustic basket billiard and a tin of Dunhill Standard Mixture Mellow. After a few bowls, I snapped the tenon knocking the pipe on the rim of the wastebasket and tossed it, but kept the tin.
This spring, I picked up another basket pipe and have sampled nearly a dozen blends. I've got a handful of pipes in daily rotation now, cobs and briars. So far, I favor American burley-based aromatics as well as a couple Virginias and an English or two. I smoke a couple bowls a day. I have more Canadians than any other shape and generally prefer straight pipes.
Thanks to the virtual mentoring of this web forum, I've learned a lot quickly and enjoy every bowl. Having a blast!