What are you thoughts on courting strangers?

I’ve noticed a semi-significant amount of questions in the last couple weeks directed towards coming on to/asking out strangers in the workplace, school, etc. I’ve also noticed a fairly varied amount of responses to these questions, ranging from advice (which I’m assuming means the answerer supports this action) to cautionary tales about how the other person might be involved with someone to Flutherites flat-out saying that it’s probably a bad idea.

So what are YOUR thoughts? Bad idea? Good idea? Under what specific circumstances do you think it’s O.K and under what circumstances do you think it’s best to just let the crush run its course and be done with it?