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My theory as to why anons like tomboys is because we all met this one girl in our lifetime that was not only super friendly to us, but had similar interests and was all around a cool person to hang out with.
But because we're all socially awkward autistic fucks otherwise we wouldn't be on 4chan much less /co/, we never had a chance with her. So we try to recapture that feeling with tomboy waifus, but that feeling will never truly be fulfilled, and so we plunge ourselves into degeneracy to try and fill that hole.
That hole is a bottomless pit.