I think the key point is having a zero harassment policy. It should not matter if the victim/subject of the harassment appears to be tolerating it (or even enjoying the attention). Chances are he/she is just being a good sport and is socially intimidated.

The worst thing about harassment culture (even when it's largely good-natured) is that it creates and reinforces a power dynamic and subtle "law of the jungle" status hierarchy where the most inappropriate, brazen harasser becomes the dominant figure.

In my opinion, this is particularly dangerous in the way that it obstructs critical thought and group problem solving. Not necessarily relevant to high school but highly important if a team of coworkers evolve toward such a culture.