I originally took MineralMan's OP to be talking about legal standards, but he clarified that he wasn't addressing laws, just morality.

Each of you condemns the behavior of a man who presses on after getting an initial No. My question is whether, aside from whether he's acting morally or fairly or sensibly, do you think he's acting illegally (under the laws we have now or as they should be)? If, after the further conversation, either of the women who initially said No then says Yes and they have sex, but she subsequently reports the incident to the police, should the district attorney prosecute him (for rape or sexual assault or whatever)? If you were on the jury, would you vote to convict him?

My own view is that the man in Example 1 is selfish and insensitive, and both he and the women in his life would be better off if he took a more mature view of relationships; the man in Example 3 is acting responsibly and appropriately; but the law does not and should not criminalize what either of them has done.