When it comes to getting what you want out of a social interaction, or letting someone know what you want out of it, there are four "stages" at your level of skill to do it. As an example, let's say someone is hungry, needs to go eat, but is currently in the middle of a conversation and needs to end it before they can go eat.

Stage 1: This person knows how to naturally wind down the conversation to get it to naturally end in a satisfying way, or they can make the other person think it was their own idea to end the conversation.

Stage 2: This person knows how to identify natural breaks and lulls in conversation, and can wait for when one will happen, and once it does, can mention they're hungry, and end the conversation to go eat.

Stage 3: This person can't identify the breaks in conversation. While mid-conversation, they might just say "I'm hungry" and leave, abruptly and seemingly rudely.

Stage 4: This person does not know at all how to advocate for themself. They may not even know how to actually even describe how they're feeling with words. They will never end the conversation or even mention that they're hungry. If the conversation doesn't end on its own, they will eventually just collapse from starvation.

Society puts emphasis on not being rude or creepy. To an outside observer, someone going from Stage 4 to Stage 3 looks like a step backwards, like they just started getting rude, but what they don't realize is that the problem the person had still existed and was still causing trouble, they just didn't even communicate until reaching Stage 3. However, for the most part, it is impossible to skip stages, you can only go from Stage 4 to Stage 3, Stage 3 to Stage 2, and so on, not anything like Stage 4 to Stage 2, or Stage 3 to Stage 1.

To apply this to dating, most of the guys who are asking for advice or complaining about how hard it is are in Stage 4, or the very early parts of Stage 3. A lot of advice that emphasizes not being creepy is basically saying "Be at Stage 1 or 2, but don't touch Stage 3, Stage 3 is evil". But if you're in Stage 4, you can't just skip Stage 3. And a lot of the complaints about that kind of advice usually comes from the guy knowing that he can't avoid Stage 3, but has a hard time really communicating it.

What they need to hear is "You will spend some time at Stage 3 as you get better, and that's OK".