[ghusto]

It’s inappropriate if it’s inappropriate. Not that hitting on a woman is inappropriate in itself.

Think of it the other way around: You send an email trying to quickly schedule an appointment with someone, and they reply with a time, and flirt with you. It’s weird because there’s no context for that.

[huytersd]

It seems arbitrary. Plenty of people hit on each other in professional settings or the workplace all the time.

[yowzadave]

There's a TV show starring Stephen Merchant from a few years ago called "Hello Ladies", in which he plays a character who is constantly hitting on (and being rejected by) models and actresses. He has a frequent complaint when he gets shut down for behaving inappropriately: "What are the rules?!?"

It's frustrating for people who are less socially adept to learn that, in some cases, there are no hard and fast rules.

[huytersd]

I think it’s less about “not getting the rules” and more of who made those rules because society doesn’t agree on them in a unified way by any means.