How did you start smoking pipes?

My father smoked a pipe. Gave me a basket pipe when I was 19, purchased at the original Tinder Box in Santa Monica. That was an amazing store. Next three pipes were gifts from my wife, the first as a wedding present; mid 70's. That first one was a beatiful Sven Lars freehand. Will always be my favorite, even though I don't smoke it often anymore.
As a note, I recently ran into one of the apprentice pipe smiths from that particular Tinder Box. He own a pipe and cigar shop in Palm Desert, California now. Spent hours one evening in that shop smoking and chatting about Tinder Box. An evening I won't forget for some time. 

Interesting side note, Kennedy loved Cuban cigars too, so before he put the ban on them, he stocked up so that he wouldn't be without them.

My father was an all day, every day pipe smoker and occasional cigar smoker. He usually bought inexpensive pipes at the BX as he had a tendency to drop and/or lose them. I started working when I was thirteen and with money in my pocket, I started buying him nice pipes for his birthday and Christmas. I enjoyed going to the smoke shops and picking them out as much as he enjoyed smoking them. So I was a connoisseur (or at least an admirer) of pipes long before I smoked them.

Many years later, my best friend from high school was working in Europe and surprised me with a box of very good cigars from the magic isle. They were very strong and sent my head spinning, but I smoked them on special occasions with my father. I made a point of doing this each time one of my children were born.

Several years after my father died, I stopped into the smoke shop and picked up a few Macanudo Maduros, a pipe (Butz-Choquin Castel Ultra), and a tin of Dunhill Early Morning Pipe. In addition to being my father, he was also my best friend and losing him was very difficult for me. I actually didn't enjoy growing up in a cloud of smoke, but after he was gone, pipe smoking was a way to remember him.

I enjoyed the maduros and scorched my mouth royally attempting to smoke the pipe.  Otherwise, I enjoyed pipe tobacco, eventually learned how to smoke a pipe correctly, and here I am.  I don't consider myself a smoker like my father was, I'm more of a hobbyist and limit my smoking to my shop, as I don't want my family to have to "live in a cloud" like I did.  I never have smoked my father's favored Sir Walter Raleigh tobacco, and don't intend to, but I did pick my SWR avatar in remembrance of him.

Almost 30 years ago, when I first started dating the young lady who would eventually become my wife, I smoked Marlborough Lights, only about a pack a week. My new girlfriend told me she wouldn't lick an ashtray and she wouldn't kiss a man who smoked cigarettes. She hated the smell. So I tried a pipe, and she loved it. The rest, as they say, is history. I think that first pipe was a Dr Grabow from the drug store, and that first tobacco was either Borkum Riff or Captain Black.