This is a society-wide problem. Flirting, dating, attraction, these are all skills, and like all skills, require making mistakes and learning from them in order to improve on them. However, there is practically zero tolerance in men making mistakes in this area.

One example:

A man misreads signs, thinks that his friend is into him, so he tries to make this friendship into something more. The result? She is now uncomfortable with him, she doesn't want him around, she tells their mutual friends about him, the entire circle, at best, feels they cannot have him around women, at worst, doesn't want him around anymore and ostracizes him. Yet it was necessary for him to make that mistake to learn from it, learn what is and is not a sign.

Could you imagine this reaction for any other skill? Like, what if, when someone wanted to learn how to dance, they would get belittled and ostracized for making the normal kind of mistakes you would make just because you're still learning? Would ANYONE want to learn how to dance then?

This hostile environment is a major obstacle.