This has been the story of my life. I think there is a certain type of person - physical attractiveness is part of it, but charisma is even bigger – who can "get away with" flirting in unsanctioned spaces. It's a combination of being confident enough to break taboo, perceptive enough to read subtle interest cues, and being attractive enough for those interest cues to be non-zero.
I've tried to be that person from time to time, but it almost always breaks down on one of those axes, thus consigning most of my dating efforts to the soul-crushing grind of dating sites/apps.
I think the real unwritten rule is, don't flirt with someone unless you're reasonably confident that they'd like to be flirted with. Some people might be able to figure that out in a matter of minutes, and others might need to get to know someone over the course of weeks or months in a casual group setting to figure it out.
I am sorry to say, but I think people who believe flirting is not allowed probably have not put in the effort to be able to read social cues, don't have an aptitude for it, or never learned to flirt in a non-offputting way.
I think people have been dealing with rejection forever. Everyone has to start out awkward, and most people get over it.
Maybe that is one place where technology hurts us. Maybe 30 years ago, a young person would have tried and struck out, and then they would have gotten over it and tried again. Whereas maybe today people try and fail, and then they can retreat into video games and online communities, which offer a superficial sense of success or belonging without the same risk of direct rejection.
I agree that if you're charming and fun, flirting with strangers is pretty straightforward, and I especially agree with the point about getting to know people over a longer period of time before trying to gauge potential interest. Worst case, you get a cute friend!
That's totally true! But that's one thing about flirting, it can be very light and non-committal.
If she is being extra friendly, smiling a lot, and giving you a little extra eye contact, you can do the same and see how she responds. If she gives you a positive feedback, take it one step farther. If she gives you negative feedback, just forget about it no harm done.
Maybe she was smiling at you in the first place because she also doesn't know if she wants to flirt with you and she's testing the waters.
I think where people get into trouble is they see someone go from 0 to 1, and they jump straight to step 7 which comes off as aggressive and off-putting.