> Asking them five times is almost certainly harassment.
Yet this behavior is romanticised is popular culture, and has been from the dawn of time up to and including the present: Oddyseus and Helen of Troy, Shakespeare's "The taming of the shrew", tons of Fred Astaire movies, as well as modern movies like "Ghost", "Life is beautiful", "Chasing Amy", TV shows like "Sex and the city"... I could go on. Lucikly I don't need to, since TVtropes has a site dedicated to this character (the "dogged nice guy"). And note that many of these are targeted at, and very popular with, women (who are usually at the receiving end of the initially-unwarranted attention). Apparently this behaviour can walk a thin line between illegal and very very romantic.