Reading the room, knowing when and how it's appropriate to show interest, etc are skills, and like all skills, require making mistakes in order to get better.

Oftentimes, there are discussions in which a guy says "I don't know how to approach or show interest in a woman without being creepy."

Usually, someone will reply "It's not that hard. Read the room."

The first guy will probably not be satisfied with that reply. There's a reason for that. Presumably, he does not know how to, or is not good at reading the room. This is because that is a skill which he needs to improve at. However, the way he improves at the skill is practicing. Practicing will involve making a lot of mistakes, but learning from them. One problem there, society has basically made it unacceptable to make mistakes in that regard. If he makes mistakes there, it's creepy, he's in the wrong, he might be hurting her.

Furthermore, the more times he shows interest in women who are in or near his social circle, the more likely he is to gain a bad reputation. A reputation of being the guy who hits on any woman just because she's a woman. The fact that this will happen also contradicts a central aspect of how practice works, in that it's supposed to be repetitive. You need to keep doing it over and over again on order to improve. However, doing it over and over again will get a guy a bad reputation, and yes, seen as creepy.

There are no other skills like this. Many people like ice skating. However, if there was a large contingent of people who would shame and shun people for being bad at ice skating, because "well, I don't want any bad ice skater to run into me and hurt me", and the general consensus of these people is not that they're just bullies or assholes, but they're righteously angry at people who hurt others while ice skating, because some bad ice skaters try doing a quad axel in a crowded skating rink when they don't know how, and they have no way of knowing which bad ice skaters would do that, nobody would probably ever want to take up ice skating, right?

When a guy says "I don't know how to show interest in a woman", there's way more to the question. What he's really saying is "I know that something is wrong, and I need to improve, but any avenue there is for improvement is almost completely closed off due to all the hostility there is towards trying to improve here. I don't know how I can improve at this without hurting myself and others."