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I smoke a pipe about 10 times a year and it never interfered with my dating life, probably because I usually only smoke it when I am deep in the wilderness camping with my dogs. I am also a professor at a private college who wears tweed jackets with leather patches on the elbows from time to time, so I don't think any woman I dated would be that surprised to find out I occasionally light up.
For me it is all about the ritual. First I make a fire, and when the fire gets nice and hot and I have a nice bed of coals I make a pot of super strong black coffee. When my thermos of coffee is about half empty, I light the pipe and I smoke it very slowly over the course of an hour or two. I like English tobacco with a high percentage of latakia, although I like cavendish as well. I have the most amazing clarity of thought over that hour, and I find it a good way to make important decisions.
I would not want to smoke every day, but I have a very thorough understanding of statistics and biochemistry and I find the risk associated with my usage pattern well within the acceptable range.
All depends on what you put in that pipe. Crack cocaine - no. Everything else, fair game. Pipe tobacco smells good and other stuff... well, you know. But then again, I am not a woman.
The one downside, is it makes you *look* like a g̶i̶a̶n̶t̶ ̶d̶o̶u̶c̶h̶e̶ pretentious snob, who's attempting to appear better than everybody, but is failing. But then again, I smoke cigars, so opinions vary.