FlexpertHamilton
Master Don Juan
It depends entirely on the cirumstances. In text/social media/dating apps, i'd say no. If it's nightgame, I'd also generally say no for the same reasons: most guys hitting on them are probably saying the same **** as you. If it's daygame, however, I'd say yes, because it takes balls to do that **** in the middle of the day and they're not expecting it.
There is no rule of thumb, though. I'd strongly avoid using top shelf compliments such as beautiful, gorgeous, etc (unless they truly are, a 9/10 dressed super feminine and elegant in a grocery store for instance, would warrant such strong adjectives).
Generally though, I think it's best to make specific compliments over something generic. Maybe say their winged eyeliner looks good, or say the color of their dress looks good on them, or whatever. Or maybe spin it into a half compliment and say that dress looks good on them but the color seems off. If you are ballsy you could take the late Patrice O'Neal approach and open with something like "look at you in those shorts!" with an objectifying tone, but that probably takes a very precise mix of tenderness and aggressiveness.
There is no rule of thumb, though. I'd strongly avoid using top shelf compliments such as beautiful, gorgeous, etc (unless they truly are, a 9/10 dressed super feminine and elegant in a grocery store for instance, would warrant such strong adjectives).
Generally though, I think it's best to make specific compliments over something generic. Maybe say their winged eyeliner looks good, or say the color of their dress looks good on them, or whatever. Or maybe spin it into a half compliment and say that dress looks good on them but the color seems off. If you are ballsy you could take the late Patrice O'Neal approach and open with something like "look at you in those shorts!" with an objectifying tone, but that probably takes a very precise mix of tenderness and aggressiveness.
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