I've flirted with female coworkers before. Other than this one female coworker at a past job who showed off (what I thought were) some pretty severe dtf clues, I try to only do mild flirts (so that way I can pass off the flirts as mere friendliness if need be).The only place this could be an issue is at work which is on the guy anyway since they shouldn't be looking to bang women at their job.
And this is only an issue if done repeatedly where the woman already turns them down and they continue asking.
It's not harassment to ask once. It's harassment when they continue to ask after they already were declined.
So again, this means they did what they shouldn't do not once but multiple times, and usually more than 2 because most women don't want to go to HR until it becomes absolutely necessary and they feel like they have no other choice to get it to stop.
But the bigger issue is why does it happen in the first place? Because most guys these days have no social skills, no tact, no conversational skills and are very awkward when talking to other people, especially women.
It's at the point I just shake my head at some of the stuff I see the younger generations doing.
Social media first became big as I was entering high school. I think that's why my generation (and the generation behind me) are more awkward with women compared to previous generations. We were hiding behind a screen during our teen years (the years when it's crucial to develop your skills with girls)