Ehh for some it's natural to understand, for some it's learned, for some it's off the radar completely.
Asking for compliments is fine but people are insecure so they do it indirectly.
"How do you like this dress/these pants/this whatever" would be someone giving an opportunity to compliment them. But they would be uncomfortable with asking, "can you compliment this ..."
You're right that it's not <good> communication. It's super taxing for me as i'm in the learned group edging on off the radar(i naturally interpret teasing as bullying). So i just try to compliment people regularly at least once every time i spend time with them to make up for it. More on dates and in relationships.
It can depend on the person so it's a general concept. I think if someone is asking for a critique they would ask more directly. Culture also plays a big role. I'm speaking from a USA cultural viewpoint.
Bah, screw that! People like making others feel good. It makes you feel good to know another person is pleased. So what if you fish for that sort of engagement unless you're being an incessant little dictator?
How do you like this dress/these pants/this whatever” would be someone giving an opportunity to compliment them.
I am 42 years old, married for 15 years, together with my wife for >23 years. And this is the first time I realize that she doesn't really mean the clothing but is fishing for a compliment. It never occurred to me, and it seriously is blowing my mind.
Edit: rotfl, all the occasions she asked me this kind of question suddenly make sense. Damn, I think I have to apologize.
Lol took me until my 30's. This is the problem with modern masculinity, we are not taught about social norms. So those of us who have trouble with them struggle. In any case, I hope you and your wife are better for the realization!