FWIW, I happen to have worked with and even hired a fairly large number (maybe 5) of folks that once worked for Playboy. As far as I could tell (and certainly a

FWIW, I happen to have worked with and even hired a fairly large number (maybe 5) of folks that once worked for Playboy. As far as I could tell (and certainly as far as I was concerned) there was no stigma associated with this, even at moderately conservative publishing companies. And I think most people would rate a soft-core porn site like Playboy as more controversial than dating sites. It's hard to tell from your post how scuzzy the site you're talking about really is (based on your concerns, maybe it is worse than we think?), but unless it is a fairly transparent front for something illegal (prostitution or whatnot) I don't think you have a lot to be concerned about. If the only thing that makes this more controversial than OKCupid or LavaLife or the personals section of Craigslist is that it is targeted at a gay audience, I definitely wouldn't worry about this. You probably wouldn't want to work for someone who is bothered by that difference anyway.