“One thing that is bothering me about this conversation: If it’s untznius for people to go out more than a handful of times, or to have more casual dates (even though it’s for toeles), why is it okay for men to be talking to women online (and telling them that the way they date is untznius).”
Lilmod,
I don’t mean to pick on you but one of my pet peeves about words like “tznius” and the overly broad way they are used in our circles is that it obfuscates what is “grey area” as you put it, and what is black on white halacha pesuka. Schok and Kalus rosh with arayos is a gezeira d’rabbanan for which the punishment is lashes (makos mardos).
Talking to women online in a manner that is not schok or kalus rosh is not forbidden by a gezeira. It might be in some circumstances and among some communities “untzniusdik” according to their standards. But that sort of “tznius” is an organic concept of Daas Yehudis, something that fluctuates and changes with the time and place. The two cannot be compared.
Just because you feel it is necessary for singles to engage in schok and kalus rosh is insufficient to be mevatel a gezeiras chazal. It would take very broad shoulders to declare a horaas shoh.