Speech is messy. Sexualized speech is especially messy. Freedom of expression in abstraction is easily professed, yet often controversial and unsatisfying. As states attempt to balance the interest of liberty, speech is often at the intersection. In its practical application, it is easy to lose sight of the interest of expression, as the damage of the expression is much more concrete than that of the abstraction of speech ideals. This work is a unique, comprehensive study of sexualized speech regulation, reviewing the paradigms of enforcement and looking forward to determine how governments will react to challenges in an interconnected world. A challenge will be to find a balance between freedom of expression and protection of societal interests. Challenges of the freedom of expression are many and often. Often restrictions seem reasonable and justified. The ideal of free expression is often more noble than the speech that is suppressed. It is particularly because of the unpopularity of some of this sexualized speech and some speakers that eternal vigilance may be required.