I think the reason Hollywood needs to represent love as something to be conquered through stalking and not respecting women's boundaries is because that was and is reality, and the men financing, producing, directing, and acting in those movies all performed such acts.

By accepting the reality that women's boundaries are very much set out of a dislike and disinterest of the man pursuing them and not because they are playing “hard to get” or simply don't know what's best for them, most men would have to accept that some of their “romantic” actions weren't romantic at all.