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This is because women under "normal circumstances" are the objects of desire which are fought over (I'm sorry if that sounds harsh, but that's biology for ya). Be it glaring, trying to make eye contact, or cringe worthy songs, those are just people trying to court those objects.
-The most common reason why women find it cringe worthy is because, women don't find these men as objects of desire (too poor/ not good looking/ dress bad etc.) .
The moment a woman finds a man who is an object of desire for HER, doing THE EXACT SAME THING, that "EWWWWW" turns into "AWWWW" faster than a heart beat.
-Ironically enough, there are situations in which the guy is the object of desire (fame/ fortune/ good looks)...
suddenly the girls and women who were finding guys cringe worthy convert into the same cringe worthy animals they complain to their girlfriends about;
-Oh and
just in case you think it's just the celebs that get the attention, ask tall guys who hit the gym regularly or play some sport in their colleges and unis, they'll tell ya. At this point I think, its human craving to get attention, just that we call it cringe worthy, when it's not from someone we deem is "in our league" ...
Well
that depends on the social acceptability of that particular setting, I've seen girls with T's and skinny jeans on (frowned upon in our culture), who attend parties with that clothing and as soon as the party is over, they go back to the "shareef shalwar kameez" before going home.
You'll see girls coming from conservative backgrounds, dress all up in their abayas taking them off once they get in to universities wearing dresses that are not so conservative. That's because on the road and in the home the social acceptability is different, in university, it's a different social acceptability altogether.