Social engineering is quickly becoming more prevalent in the InfoSec industry. Users are becoming more educated about social engineering attempts, but they still fall victim to attacks. Why? Well, like all in all industries, with great improvement to technology comes great improvement to exploitation, and maybe not so great improvement to security. This presentation explores the subtleties involved in wordcrafting, tone of voice, and adaptability during – shudder – human interaction. We’ll also discuss gender roles and stereotyping and the effect it has on the victim. This presentation stemmed from an academic paper and virtual presentation done during Cyni’s coursework for CyberSecurity.