Hi jfpbookworm, long time no see. I agree with skepticism when making decisions over whether one's self-interest outweighs harm to someone else, which is why in this post I advocated weighing in the potential benefit to the other party also (emphasis added):

I think what we should really be asking is: is the technique harmful, can the user of the technique reasonably be expected to know that, and can any potential harm be justified by potential benefits to the recipient of the technique?

I think I came by this way of thinking from reading Mane Hajdin's The Law of Sexual Harassment. He wrote an article in this book that has some relevant comments (read page 297-299, though we don't get 298 in the preview):

We base our decisions on comparing the expected social utility of a practice (the magnitude of the benefits multiplied by the probability of their occurrence) with the expected social disutility or the expected social cost (the magnitude of the harms multiplied by the probability of their occurrence). [...] For at least some crude or aggressive advances we will have to conclude that the magnitude of the harm, multiplied by its probability, is so great that the advances in question are worthwhile, and that it may be desirable to have rules that prohibit them. [...] Moreover, in determining whether sexual advances of a particular kind would be worthwhile we need to compare the making of such advances not only with not making any advances, but also with making other kinds of advances that can be made under the circumstances.

He then sets up three hypothetical advances:

1. 10% chance of success, 88% chance of mild annoyance, 2% chance of offense

2. 10% success, 89% mild annoyance, 1% offense

3. 11% success, 69% mild annoyance, 20% offense

He says that advances #2 is obvious preferable to advance #1. As for advance #3, the relevant question to ask is:

whether the additional 1 percent probability of success justifies the additional 19 percent probability of offense. If the answer to that question is "no," as it may well be (that depends on the precise intensity of the offense), then we may want to discourage people from making advances of this third type and encourage them to make the advances that are less risky instead. This is exactly analogous to the reasoning that leads us to impose speed limits on motor traffic.

When pickup artists think about ethics, I suspect this is the kind of implicit moral framework they are using. Of course, all of these calculations have subjective factors, but they are better than nothing.

Exactly, thank you.