I got an email the other day that said the title "Prick Van Winkle" was just awful. Actually, I believe he said "It sucks."
Titling a story is, for me, the hardest part of writing. That's because, for me, the title should be part of the story. Sometimes I have the whole story completely written before a title comes to me. "Cattleman's Lament" was one of those that I just couldn't come up with a title for. I think that title was actually recommended by another author who I respect a lot.
When it came to this story, though, the title was the first thing that popped into my head. I liked it for a couple of reasons. First of all, it's recognizable as being, in some way, about Rip Van Winkle. But secondly, and maybe most importantly, it describes, in an ironic sort of way, what Bob Winkle was for fifty years. To the women who interacted with him, he was basically two things: He was a sounding board - someone to talk to about private and secret things and... he was a stiff prick. The women interacted with him normally - talking to him - but a most important facet was that part of him that would have been denied them, had he been awake.
So, you see, the title isn't meant to shock, as much as it's meant to identify the major things about him that made him special. He was a descendant of Rip, and to the women, he was a prick that continued to create more of Rip's descendants, even though he didn't know it at the time.
Just thought you might want to know.