In the current era (where misreading a false dtf clue can lead to harrassment accusations), this is serious business.
What a woman would have brushed off as mere cringeworthiness in 2003, she'll call harassment in 2023. And it can ruin the guy's life.
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.