From long experience, I am tempted to sum it all up with one word: Don't. I got a friend into a huge amount of trouble (sorry, Jen) which wasn't worth the story itself. If you think that you can do the story and not make a nuisance of yourself, make sure you explain everything to your friend: NowPublic is available around the world; there's a good chance that the worst possible person will read the story; it'll hang around forever, and may cause perpetual embarrassment; etc. etc.

Finally, don’t argue: if your friend says fuggedaboudit , drop it.