I guess I represent one of the younger demographics around here, raised entirely after pipes had their 1960-70 heyday. Raised by ex-smokers I rarely had any contact with smoking of any sort growing up. The only pipe smoker I knew was the father of a friend. I didn't really think anything about it one way or the other, except for the distinctive way their house smelled when you walked in the door. Not bad, just distinctive. Pipes are a part of the books that I read both growing up and as a YA: Tolkien, Sherlock Holmes, Wheel of Time. I'm sure there are others I've missed. But I was still pretty anti-smoking.
Then one day when I was golfing with my wife and another couple, the other fella offered me a cigarillo to smoke on the course. I refused (politely), but afterwards my wife asked me why. She said she liked the smell and I should have tried it.
It's a little thing like that that lodges in the back of your brain. Years later, after watching a Lord of the Rings movie, a little curiosity led to some Googling, which found me pipes.org and ton of other sites and I found myself learning a lot. I found a good B&M here who answered some questions, and I found myself kitted out with a briar, tamper, matches, filters, pipe cleaners and 25 g of a house burley blend for about $80.
It's still just an occasional thing for me. I have TAD urges, but everything's so expensive in Canada it's easy to fight off some days. My wife loves the smell on me so I tend to canvas her opinion on the tobaccos. Turns out her grandfather smoked a pipe, so that's probably something lodged in the back of her brain...
Simon