General Discussion

only if it is repetitive after the woman has indicated that she is not interested. But this can depend on the context, too. For example, if he locks his office door after she enters and makes a pass at her, that is more than just flirting.

Or, he might threaten retaliation by making false complaints about her work to her boss if she does not accept his attention. That's coercion, not flirting.

When it is an imbalanced power situation, it is inappropriate because of reasons already given, that she might fear retaliation if she says no. But, if she says no and he accepts it without rancor or retaliation, it's a little more gray. If she says she is uncomfortable around him because he paid attention to her, and he sincerely apologizes for that because he misread her and thought she was interested but now knows he was wrong, it's also a bit gray.

Men can avoid the problem altogether by being strictly professional at work with women. And vice versa, because it does happen the other way around, too.

The occasion when he asked a woman if he could kiss her was a social setting, not work.