Eh, I think restraint beyond "don't ask someone out five times, like a creep" is called for. I don't know of you've ever had anything ... distinctive about your appearance -- really thick glasses, unusually tall or short, uncommon facial hair style, hypnotic voice -- but attention, even non-creepy compliments ("your beard is awesome, can I touch it?") get really draining after awhile. Each individual's interest isn't a problem, it's the never-ending trickle that just wears away at you.

It's not just that someone might have to deal with an overwhelming amount of unwanted interest from a single person, but that the aggregated polite inquiries from dozens or hundreds of interested coworkers and colleagues could add up to something overwhelming. It's like littering.

So while being in a relationship with a co-worker may be fine, starting a relationship with a co-worker is tricky. It's like why you shouldn't hit on wait staff or flight attendants: they are there because it is there job. Your co-workers come into work every day for the same reason.

> 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.

Thank you for not linking to TV Tropes. I've lost a great many hours to that site. :)

Yes, it was a deliberate non-link ;)

(Oblig. http://xkcd.com/609 )

As I recall it, Odysseus was just one of many suitors of Helen and in fact had to be strong-armed into joining the Greek invasion. Might you perhaps be thinking of Penelope?

(Also "The Taming of the Shrew" is firmly in the "oh fuck no" category of 21st century society)

It goes both ways. Numerous female pop stars, and in entertainment in general, angling and fishing to steal away the guy from his relationship because she KNOWS they are meant to be together... She doesn't hear "No thanks" and go away.