You think he would feel bad after mistreating the Tomboy in question after finding out she’s female?
I can totally imagine that!
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I feel like Sanji would somehow just know it’s a woman. Sanji doesn’t just consciously choose to not hurt women, it’s also a subconscious thing. He unknowingly weakens himself enough to not hurt women when he confronts them.
So knowing Sanji, just like how he is able to read and find the intentions of women, he’d somehow just know whoever he was fighting was or was not a woman.
If this is possible, why not the other way around?
If the said tomboy a truly man at heart, and behaves accordingly, shouldn't Sanji perceive such character as a male?
However, if the said character still thinks of herself as a female, then Sanji would feel that how he felt Tashigi's tear falling.