I had a grandfather who smoked cigars and a great-grandfather who, judging from the one photo I have of him, smoked a pipe. But the former died when I was five, and the latter was gone before I was even born. I knew no family members who smoked a pipe.
For me, it was a revelation to discover that C.S. Lewis and his brother, Warnie, were avid pipe smokers, as was their friend J.R.R. Tolkien. Their example made a huge impact on me.
As for people I actually knew, though, it wasn't until I got a part-time job at a mall Tinder Box that I really came to know and admire fellow pipe smokers. There was Matt, a part-time close-up magician at local restaurants. Fred, who worked in a factory that allowed smoking (this was in the early 80s) and smoked about 12 bowls a day in a ragged Dunhill. Phil, the retired cop who was constantly puffing at the store because anything from the open jars was free while you were working. And CJ, who eschewed pipes in favor of Churchill-size cigars. I spent four years working with those guys, and there's hardly a day that passes that I don't think of them all with great fondness. Haven't encountered a group like that since. Matt and I were pretty much the "pipe guys," and the owner allowed us to order and stock any tinned blends we wanted, so long as they ended up selling eventually. Thanks to that, I was able to try a ton of blends I'd have never encountered otherwise -- many of which are now gone forever.
Bob